Sc(Ⅲ)催化硫醇对邻亚甲基苯醌的亲核加成反应合成邻羟基苄硫醚衍生物

doi:10.7503/cjcu20180599

高等学校化学学报 ›› 2019, Vol. 40 ›› Issue (4): 725.doi: 10.7503/cjcu20180599

Sc(Ⅲ)催化硫醇对邻亚甲基苯醌的亲核加成反应合成邻羟基苄硫醚衍生物

张硕(), 于一涛, 李庆刚, 赵宁, 侯梓桐, 刘一帆, 李冰, 牟秋红, 李金辉, 王峰, 彭丹()

齐鲁工业大学(山东省科学院)新材料研究所, 山东省特种含硅新材料重点实验室, 济南 250014

收稿日期:2018-08-27 出版日期:2019-04-03 发布日期:2019-01-15
作者简介:
联系人简介: 张硕, 男, 博士, 助理研究员, 主要从事有机催化反应方面的研究. E-mail: e50687e@163.com;彭丹, 女, 博士, 副研究员, 主要从事有机催化反应和有机硅化学方面的研究. E-mail: lonarpeng@aliyun.com
基金资助:
山东省自然科学基金(批准号: ZR2017BB033)、山东省科学院青年科学基金(批准号: 2018QN0030)和国家自然科学基金(批准号: 51503118)资助.

Sc(Ⅲ) Catalyzed Nucleophilic Addition of in situ Generated ortho-Quinone Methides with Thiols: an Efficient Access to ortho-Hydroxybenzyl Thioethers^†

ZHANG Shuo^*(), YU Yitao, LI Qinggang, ZHAO Ning, HOU Zitong, LIU Yifan, LI Bing, MU Qiuhong, LI Jinhui, WANG Feng, PENG Dan^*()

Shandong Provincial Key Laboratory for Special Silicone-Containing Materials, Advanced Materials Institute, Qilu University of Technology(Shandong Academy of Sciences), Ji’nan 250014, China

Received:2018-08-27 Online:2019-04-03 Published:2019-01-15
Contact: ZHANG Shuo,PENG Dan E-mail:e50687e@163.com;lonarpeng@aliyun.com
Supported by:
† Supported by the Natural Science Foundation of Shandong Province, China(No.ZR2017BB033), the Youth Science Funds of Shandong Academy of Sciences, China(No.2018QN0030) and the National Natural Science Foundation of China(No.51503118).

摘要/Abstract

摘要：

以2-[羟基(苯基)甲基]苯酚类化合物和简单的硫醇为原料, 1,2-二氯乙烷为溶剂, 在Sc(Ⅲ)促进下原位生成邻亚甲基苯醌, 并发生亲核加成反应构建邻羟基苄硫醚. 该反应在50 ℃下搅拌2 h即可完成, 目标产物产率82%95%. 反应可放大至克级规模.

关键词: 邻亚甲基苯醌, 钪(Ⅲ);, 硫醇, 亲核加成反应, 邻羟基苄硫醚

Abstract:

Ortho-hydroxybenzyl thioethers play a vital role in chemical biology as they have anti-oxidant and anti-inflammatory properties. o-Quinone derivatives is not only a variety of active and important intermediate, but also widely used in the synthesis of natural products and medicinal chemistry. In the present study, the Sc(Ⅲ) catalyzed nucleophilic addition to o-quinone methides by thiols for the synthesis of ortho-hydroxybenzyl thioethers was developed. The reactions could be carried out with different primary thiols, secondary thiols and benzothiols. For 2-[hydroxyl(phenyl)methyl]phenols, electron-withdrawing groups and electron-donating groups on aromatic rings could react smoothly to obtain corresponding products. The structures of the products were characterized by infrared spectra, proton nuclear magnetic resonance, carbon nuclear magnetic resonance and high resolution mass spectra. The prominent features of the present strategy are wide substrate scope, mild reaction conditions and moderate to good yields. Furthermore, the reaction could be scaled up to multigram scale. A preliminary series of control experiments has been analyzed and the study on the extension to para-hydroxybenzyl alcohols for the synthesis of para-hydroxybenzyl thioethers has been achieved.

Key words: o-Quinone, Scandium(Ⅲ);, Thiol, Nucleophilic addition, ortho-Hydroxybenzyl thioether

中图分类号:

O622.7

TrendMD:

张硕, 于一涛, 李庆刚, 赵宁, 侯梓桐, 刘一帆, 李冰, 牟秋红, 李金辉, 王峰, 彭丹. Sc(Ⅲ)催化硫醇对邻亚甲基苯醌的亲核加成反应合成邻羟基苄硫醚衍生物. 高等学校化学学报, 2019, 40(4): 725.

ZHANG Shuo,YU Yitao,LI Qinggang,ZHAO Ning,HOU Zitong,LIU Yifan,LI Bing,MU Qiuhong,LI Jinhui,WANG Feng,PENG Dan. Sc(Ⅲ) Catalyzed Nucleophilic Addition of in situ Generated ortho-Quinone Methides with Thiols: an Efficient Access to ortho-Hydroxybenzyl Thioethers^†. Chem. J. Chinese Universities, 2019, 40(4): 725.

图/表 6

Scheme 1 Sc(OTf)3 catalyzed nucleophilic addition reaction by thiols3a: R1=H, R2=Ph, R3=H, R=C2H5; 3b: R1=H, R2=Ph, R3=H, R=n-propyl; 3c: R1=H, R2=Ph, R3=H, R=n-pentyl; 3e: R1=H, R2=Ph, R3=H, R=heptyl; 3f: R1=H, R2=Ph, R3=H, R=isobutyl; 3g: R1=H, R2=Ph, R3=H, R=isopentyl; 3h: R1=H, R2=Ph, R3=H, R=isopropyl; 3i: R1=H, R2=Ph, R3=H, R=cyclopentyl; 3j: R1=H, R2=Ph, R3=H, R=benzyl; 3k: R1=H, R2=Ph, R3=H, R=4-(tert-butyl)benzyl; 3l: R1=H, R2=Ph, R3=H, R=4-chlorobenzyl; 3m: R1=H, R2=Ph, R3=H, R=4-methylbenzyl; 3n: R1=H, R2=Ph, R3=tert-butyl, R=C2H5; 3o: R1=H, R2=Ph, R3=ethoxy, R=C2H5; 3p: R1=CH3, R2=Ph, R3=H, R=C2H5; 3q: R1=emthoxy, R2=Ph, R3=H, R=C2H5; 3r: R1=H, R2=o-tolyl, R3=H, R=C2H5; 3s: R1=H, R2=4-chlorophenyl, R3=H, R=C2H5; 3t: R1=H, R2=3-fluorophenyl, R3=H, R=C2H5; 3u: R1=H, R2=4-fluorophenyl, R3=H, R=C2H5; 3v: R1=Cl, R2=Ph, R3=H, R=C2H5; 3w: R1=H, R2=cyclohexyl, R3=H, R=C2H5; 3x: R1=H, R2=H, R3=H, R=C2H5

Table 1 Optimization of reaction conditionsa

Entry	Catalyst	Solvent	Temperature/℃	t/h	Yield^b(%)
1	Ga(OTf)₃	DCE	50	4	0
2	In(OTf)₃	DCE	50	4	0
3	Sc(OTf)₃	DCE	50	4	92
4	Conc. HCl	DCE	50	8	56
5	H₂SO₄	DCE	50	8	52
6	AlCl₃	DCE	50	8	62
7	Sc(OTf)₃	Toluene	50	4	72
8	Sc(OTf)₃	THF	50	4	76
9	Sc(OTf)₃	DCE	50	2	92
10	Sc(OTf)₃	DCE	50	1	75
11	Sc(OTf)₃	DCE	40	6	82
12^c	Sc(OTf)₃	DCE	50	6	78
13^d	Sc(OTf)₃	DCE	50	2	93

Table 2 Appearance, yields, melting points, HRMS and IR data for compounds 3a—3x and 4a

Compd.	Appearance	Yield^*(%)	HRMS, m/z [M+H]⁺	IR(film), $ν ~$ /cm^-1
3a	Colorless oil	92	245.0996	3290, 3263, 3029, 1596, 1582, 1488, 1454, 1340, 1269, 1234, 754, 699
3b	Colorless oil	90	259.1150	3289, 3062, 3029, 1596, 1582, 1487, 1454, 1339, 1270, 1236, 754, 699
3c	Colorless oil	86	273.1312	3291, 3029, 1596, 1582, 1487, 1454, 1356, 1272, 1233, 754, 699
3d	Colorless oil	84	287.1465	3292, 3029, 1596, 1582, 1487, 1454, 1341, 1271, 1234, 754, 699
3e	Colorless oil	82	315.1779	3290, 3029, 1596, 1582, 1487, 1454, 1356, 1271, 1234, 753, 699
3f	Colorless oil	87	273.1305	3291, 3029, 1597, 1583, 1488, 1454, 1366, 1271, 1234, 754, 699
3g	Colorless oil	85	287.1467	3290, 3029, 1597, 1583, 1488, 1454, 1367, 1273, 1233, 754, 699
3h^[43]	Colorless oil	88	259.1150	3290, 3029, 1598, 1583, 1489, 1454, 1366, 1271, 1235, 754, 699
3i	Colorless oil	86	285.1308	3289, 3028, 1644, 1597, 1489, 1453, 1365, 1271, 1235, 754, 699
3j^[44]	Colorless oil	91	307.1152	3289, 3028, 1644, 1599, 1493, 1454, 1341, 1272, 1234, 755, 699
3k	Colorless oil	95	363.1777	3289, 3030, 1647, 1599, 1488, 1456, 1365, 1271, 1236, 756, 701
3l	Colorless oil	86	341.0762	3296, 3029, 1644, 1597, 1490, 1454, 1365, 1272, 1233, 755, 699
Compd.	Appearance	Yield^*(%)	HRMS, m/z [M+H]⁺	IR(film), $ν ~$ /cm^-1
3m	Colorless oil	92	321.1305	3288, 3027, 1645, 1596, 1486, 1454, 1353, 1271, 1235, 754, 699
3n	Colorless oil	90	301.1622	3246, 3028, 1655, 1600, 1586, 1494, 1483, 1363, 1268, 1231, 749, 701
3o	Colorless oil	82	289.1257	3525, 3028, 1662, 1614, 1598, 1471, 1452, 1372, 1271, 1220, 732, 698
3p	Colorless oil	95	259.1151	3291, 3029, 1647, 1613, 1601, 1506, 1453, 1265, 1247, 702
3q	Colorless oil	90	275.1102	3392, 3028, 1501, 1451, 1266, 1240, 701
3r	Colorless oil	88	259.1151	3287, 3020, 1644, 1601, 1485, 1269, 1240, 753
3s	Colorless oil	86	279.0604	3298, 2968, 2928, 1644, 1596, 1488, 1455, 1268, 1233, 755
3t	Colorless oil	84	263.0901	3305, 2969, 2928, 1643, 1613, 1589, 1486, 1267, 1234, 755
3u	Colorless oil	82	263.0903	3305, 2969, 2928, 1603, 1506, 1487, 1269, 1226, 755
3v	Colorless oil	90	279.0605	3294, 2969, 2928, 1642, 1599, 1482, 1416, 1268, 1234, 698
3w	Colorless oil	85	251.1464	3271, 2927, 2852, 1609, 1581, 1487, 1451, 1271, 1231, 754
3x^[45]	Colorless oil	88	169.0685	269, 2968, 2926, 1612, 1597, 1450, 1265, 1226, 699
4a^[44]	Colorless oil	85	245.0997

Table 2 Appearance, yields, melting points, HRMS and IR data for compounds 3a—3x and 4a

Compd.	Appearance	Yield^*(%)	HRMS, m/z [M+H]⁺	IR(film), $ν ~$ /cm^-1
3a	Colorless oil	92	245.0996	3290, 3263, 3029, 1596, 1582, 1488, 1454, 1340, 1269, 1234, 754, 699
3b	Colorless oil	90	259.1150	3289, 3062, 3029, 1596, 1582, 1487, 1454, 1339, 1270, 1236, 754, 699
3c	Colorless oil	86	273.1312	3291, 3029, 1596, 1582, 1487, 1454, 1356, 1272, 1233, 754, 699
3d	Colorless oil	84	287.1465	3292, 3029, 1596, 1582, 1487, 1454, 1341, 1271, 1234, 754, 699
3e	Colorless oil	82	315.1779	3290, 3029, 1596, 1582, 1487, 1454, 1356, 1271, 1234, 753, 699
3f	Colorless oil	87	273.1305	3291, 3029, 1597, 1583, 1488, 1454, 1366, 1271, 1234, 754, 699
3g	Colorless oil	85	287.1467	3290, 3029, 1597, 1583, 1488, 1454, 1367, 1273, 1233, 754, 699
3h^[43]	Colorless oil	88	259.1150	3290, 3029, 1598, 1583, 1489, 1454, 1366, 1271, 1235, 754, 699
3i	Colorless oil	86	285.1308	3289, 3028, 1644, 1597, 1489, 1453, 1365, 1271, 1235, 754, 699
3j^[44]	Colorless oil	91	307.1152	3289, 3028, 1644, 1599, 1493, 1454, 1341, 1272, 1234, 755, 699
3k	Colorless oil	95	363.1777	3289, 3030, 1647, 1599, 1488, 1456, 1365, 1271, 1236, 756, 701
3l	Colorless oil	86	341.0762	3296, 3029, 1644, 1597, 1490, 1454, 1365, 1272, 1233, 755, 699
Compd.	Appearance	Yield^*(%)	HRMS, m/z [M+H]⁺	IR(film), $ν ~$ /cm^-1
3m	Colorless oil	92	321.1305	3288, 3027, 1645, 1596, 1486, 1454, 1353, 1271, 1235, 754, 699
3n	Colorless oil	90	301.1622	3246, 3028, 1655, 1600, 1586, 1494, 1483, 1363, 1268, 1231, 749, 701
3o	Colorless oil	82	289.1257	3525, 3028, 1662, 1614, 1598, 1471, 1452, 1372, 1271, 1220, 732, 698
3p	Colorless oil	95	259.1151	3291, 3029, 1647, 1613, 1601, 1506, 1453, 1265, 1247, 702
3q	Colorless oil	90	275.1102	3392, 3028, 1501, 1451, 1266, 1240, 701
3r	Colorless oil	88	259.1151	3287, 3020, 1644, 1601, 1485, 1269, 1240, 753
3s	Colorless oil	86	279.0604	3298, 2968, 2928, 1644, 1596, 1488, 1455, 1268, 1233, 755
3t	Colorless oil	84	263.0901	3305, 2969, 2928, 1643, 1613, 1589, 1486, 1267, 1234, 755
3u	Colorless oil	82	263.0903	3305, 2969, 2928, 1603, 1506, 1487, 1269, 1226, 755
3v	Colorless oil	90	279.0605	3294, 2969, 2928, 1642, 1599, 1482, 1416, 1268, 1234, 698
3w	Colorless oil	85	251.1464	3271, 2927, 2852, 1609, 1581, 1487, 1451, 1271, 1231, 754
3x^[45]	Colorless oil	88	169.0685	269, 2968, 2926, 1612, 1597, 1450, 1265, 1226, 699
4a^[44]	Colorless oil	85	245.0997

Table 3 1H NMR and 13C NMR data for compounds 3a—3x and 4a

Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3a	7.40(d, J=7.4 Hz, 2H), 7.32—7.16(m, 5H), 7.05(dd, J=7.6, 1.2 Hz, 1H), 6.91(dd, J=8.0, 0.7 Hz, 1H), 6.88—6.82(m, 1H), 5.39(s, 1H), 2.49—2.43(m, 2H), 1.23(t, J=7.4 Hz, 3H)	155.15, 139.31, 130.17, 129.21, 128.69, 128.67, 128.53, 128.51, 127.55, 125.16, 120.76, 117.60, 50.47, 26.36, 14.20
3b	7.40(d, J=7.4 Hz, 2H), 7.34—7.29(m, 2H), 7.21(ddd, J=15.4, 10.6, 4.4 Hz, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.95—6.89(m, 1H), 6.84(td, J=7.6, 1.0 Hz, 1H), 5.35(s, 1H), 2.48—2.39(m, 2H), 1.61(dd, J=14.6, 7.3 Hz, 2H), 0.95(t, J=7.4 Hz, 3H)	155.22, 139.30, 130.18, 129.21, 128.66, 128.48, 127.53, 125.11, 120.70, 117.64, 50.97, 34.33, 22.32, 13.49
3c	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=10.0, 4.8 Hz, 3H), 7.26—7.11(m, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.97—6.90(m, 1H), 6.88—6.82(m, 1H), 5.35(s, 1H), 2.49—2.42(m, 2H), 1.63—1.51(m, 2H), 1.38—1.33(m, 2H), 0.85(t, J=7.3 Hz, 3H)	155.23, 139.29, 130.19, 129.21, 128.67, 128.51, 128.49, 128.46, 127.54, 125.11, 120.71, 117.64, 51.04, 32.02, 21.01, 21.96, 13.64
3d	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=9.7, 5.1 Hz, 3H), 7.28—7.13(m, 2H), 7.03(dd, J=7.6, 1.1 Hz, 1H), 6.96—6.88(m, 1H), 6.84(t, J=7.5 Hz, 1H), 5.35(s, 1H), 2.45(tq, J=10.7, 5.3 Hz, 2H), 1.57(dd, J=14.7, 7.3 Hz, 2H), 1.31—1.26(m, 4H), 0.85(t, J=7.1 Hz, 3H)	155.23, 139.31, 130.19, 129.21, 128.67, 128.51, 128.48, 128.46, 127.53, 125.12, 120.71, 117.63, 51.05, 32.33, 30.99, 28.61, 22.23, 13.94
3e	7.40(d, J=7.5 Hz, 2H), 7.31(dd, J=9.9, 4.9 Hz, 3H), 7.27—7.17(m, 2H), 7.03(dd, J=7.6, 1.2 Hz, 1H), 6.92(dd, J=8.0, 0.6 Hz, 1H), 6.86—6.82(m, 1H), 5.34(s, 1H), 2.45(tq, J=10.8, 5.3 Hz, 2H), 1.60—1.56(m, 2H), 1.32—1.23(m, 8H), 0.86(t, J=6.9 Hz, 3H)	155.25, 139.29, 130.18, 129.21, 128.66, 128.54, 128.49, 127.53, 125.09, 120.70, 117.65, 51.08, 32.34, 31.67, 28.92, 28.80, 28.77, 22.61, 14.09
3f	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=13.8, 6.6 Hz, 3H), 7.21(ddd, J=11.3, 8.7, 4.4 Hz, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.92(dd, J= 8.0, 0.6 Hz, 1H), 6.87—6.80(m, 1H), 5.31(s, 1H), 2.35(qd, J=12.5, 6.8 Hz, 2H), 1.83(dt, J=13.4, 6.7 Hz, 1H), 0.95(dd, J=8.0, 6.8 Hz, 6H)	155.26, 139.36, 130.24, 129.22, 128.66, 128.51, 128.48, 128.45, 127.54, 125.12, 120.69, 117.65, 51.54, 41.27, 28.24, 22.22, 21.98
3g	7.40(d, J=7.4 Hz, 2H), 7.36—7.26(m, 3H), 7.21(ddd, J=17.1, 11.2, 4.3 Hz, 2H), 7.03(dd, J=7.6, 1.1 Hz, 1H), 6.92(d, J=7.7 Hz, 1H), 6.84(t, J=7.5 Hz, 1H), 5.35(s, 1H), 2.48—2.43(m, 2H), 1.61(dt, J=13.3, 6.6 Hz, 1H), 1.50—1.45(m, 2H), 0.84—0.81(m, 6H)	155.22, 139.26, 130.19, 129.23, 128.66, 128.51, 128.49, 128.46, 127.54, 125.06, 120.71, 117.64, 51.03, 37.92, 30.36, 27.40, 22.32, 22.15
3h	7.49—7.34(m, 3H), 7.30(t, J=7.4 Hz, 2H), 7.26—7.14(m, 2H), 7.04(dd, J=7.6, 1.2 Hz, 1H), 6.92(d, J=8.0 Hz, 1H), 6.84(t, J=7.5 Hz, 1H), 5.41(s, 1H), 2.77(dt, J=13.4, 6.7 Hz, 1H), 1.29—1.24(m, 6H)	155.30, 139.28, 130.09, 129.19, 128.67, 128.48, 127.50, 125.11, 120.73, 117.73, 50.13, 35.76, 23.07, 22.85
Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3i	7.40(d, J=7.3 Hz, 3H), 7.30(t, J=7.4 Hz, 2H), 7.26—7.13(m, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.97—6.88(m, 1H), 6.85(dd, J=10.8, 4.1 Hz, 1H), 5.36(s, 1H), 2.91(p, J=7.0 Hz, 1H), 1.91(dt, J=12.3, 6.3 Hz, 2H), 1.72—1.70(m, 2H), 1.64—1.50(m, 4H)	155.33, 139.37, 130.05, 129.15, 128.64, 128.46, 128.44, 127.47, 125.36, 120.70, 117.71, 51.40, 44.23, 33.65, 33.20, 24.88, 24.74
3j	7.36(d, J=7.3 Hz, 2H), 7.30(t, J=7.3 Hz, 4H), 7.27—7.22(m, 2H), 7.18(dd, J=12.7, 4.5 Hz, 3H), 6.95(dd, J=7.7, 1.3 Hz, 1H), 6.90(d, J= 8.4 Hz, 2H), 6.86—6.79(m, 1H), 5.11(s, 1H), 3.59(d, J=3.2 Hz, 2H)	155.03, 138.75, 137.28, 130.31 , 129.30, 129.01, 128.99, 128.76, 128.73, 127.65, 127.47, 124.86, 120.80, 117.60, 49.68, 36.54
3k	7.34(dt, J=14.9, 7.8 Hz, 6H), 7.27—7.19(m, 2H), 7.15(d, J=8.2 Hz, 2H), 6.99(s, 1H), 6.96—6.90(m, 2H), 6.88—6.79(m, 1H), 5.14(s, 1H), 3.59(d, J=2.5 Hz, 2H), 1.32(s, 9H)	155.14, 150.39, 138.73, 134.04, 130.35, 129.27, 128.73, 128.67, 128.64, 127.59, 125.59, 124.78, 120.70, 117.64, 49.97, 36.13, 34.57, 31.37
3l	7.36—7.18(m, 8H), 7.11(d, J=8.4 Hz, 2H), 6.99(dd, J=7.6, 1.3 Hz, 1H), 6.93—6.81(m, 2H), 6.78(s, 1H), 5.12(s, 1H), 3.56(s, 2H)	154.87, 138.61, 135.81, 133.18, 130.32, 130.29, 129.35,128.81, 128.75, 128.64, 127.70, 124.63, 120.88, 117.52, 49.65, 35.89
3m	7.40—7.29(m, 4H), 7.26—7.17(m, 2H), 7.13—7.08(m, 4H), 6.96(s, 1H), 6.93—6.90(m, 2H), 6.83(t, J=7.4 Hz, 1H), 5.09(s, 1H), 3.56(d, J=5.1 Hz, 2H), 2.33(s, 3H)	155.08, 138.74, 137.14, 134.11, 130.31, 129.41, 129.26 , 128.90, 128.79, 128.71, 127.61, 124.87, 120.74, 117.62, 49.64, 36.21, 21.20
3n	7.61(s, 1H), 7.42(d, J=7.4 Hz, 2H), 7.34(t, J=7.4 Hz, 2H), 7.30—7.21(m, 2H), 6.74(dd, J=7.2, 5.3 Hz, 2H), 5.35(s, 1H), 2.46(q, J=7.4 Hz, 2H), 1.44(s, 9H), 1.25(t, J=7.3 Hz, 3H)	154.38, 138.88, 138.29, 128.82, 128.63, 128.04, 127.56, 126.66, 125.19, 119.80, 77.36, 77.05, 76.73, 51.54, 34.93, 29.76, 26.27, 14.24
3o	7.47(d, J=7.4 Hz, 2H), 7.28(t, J=7.5 Hz, 2H), 7.22—7.08(m, 2H), 6.81(t, J=8.0 Hz, 1H), 6.71(dd, J=8.0, 1.1 Hz, 1H), 5.98(s, 1H), 5.66(s, 1H), 4.10—4.02(m, 2H), 2.44(q, J=7.4 Hz, 2H), 1.41(t, J=7.0 Hz, 3H), 1.23(t, J=7.4 Hz, 3H)	145.71, 143.18, 141.48, 128.38, 128.35, 127.33, 126.88, 121.02, 119.63, 110.09, 64.57, 46.17, 26.31, 14.92, 14.31
3p	7.40(d, J=7.5 Hz, 2H), 7.31(t, J=7.4 Hz, 2H), 7.26—7.22(m, 1H), 7.12(s, 1H), 7.00(dd, J=8.2, 1.7 Hz, 1H), 6.83(dd, J=8.1, 4.9 Hz, 2H), 5.34(s, 1H), 2.48(dd, J=7.4, 4.0 Hz, 2H), 2.21(s, 3H), 1.25(t, J=7.4 Hz, 3H)	152.92, 139.33, 130.56, 129.85, 129.72, 128.65, 128.45, 127.48, 124.56, 117.49, 50.76, 26.36, 20.57, 14.16
3q	7.41(d, J=7.4 Hz, 2H), 7.32(dd, J=10.1, 4.7 Hz, 2H), 7.25(t, J=7.2 Hz, 1H), 6.86(d, J=8.8 Hz, 1H), 6.76(dd, J=8.8, 3.1 Hz, 2H), 6.63(d, J=3.0 Hz, 1H), 5.34(s, 1H), 3.70(s, 3H), 2.48(qd, J=7.4, 2.0 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	153.54, 148.85, 139.05, 128.66, 128.64, 128.49, 128.44, 127.56, 126.25, 118.26, 115.74, 113.95, 55.66, 50.59, 26.35, 14.18
3r	7.54—7.51(m, 1H), 7.29(s, 1H), 7.23—7.11(m, 4H), 6.94(ddd, J=11.9, 7.9, 1.0 Hz, 2H), 6.83—6.80(m, 1H), 5.52(s, 1H), 2.51(q, J=7.4 Hz, 2H), 2.39(s, 3H), 1.27(t, J=7.4 Hz, 3H)	155.18, 137.18, 136.28, 130.73, 129.94, 128.98, 128.62, 127.48, 126.47, 125.15, 120.79, 117.44, 46.90, 26.47, 19.31, 14.16
3s	7.34(d, J=8.5 Hz, 2H), 7.22(ddd, J=11.3, 8.7 Hz, 4.7 Hz, 2H), 7.08—7.03(m, 2H), 6.93—6.85(m, 2H), 5.36(s, 1H), 2.47(qd, J=7.4, 2.0 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	154.95, 137.91, 133.29, 129.97, 129.84, 129.35, 128.78, 124.75, 120.86, 117.63, 49.68, 26.37, 14.12
3t	7.30—7.26(m, 1H), 7.21(ddd, J=12.9, 9.8, 4.7 Hz, 2H), 7.14(dd, J=10.1, 2.0 Hz, 1H), 7.06(dd, J=7.6, 1.3 Hz, 1H), 7.01(s, 1H), 6.97—6.86(m, 3H), 5.38(s, 1H), 2.49(qd, J=7.4, 1.6 Hz, 2H), 1.26(t, J=7.4 Hz, 3H)	164.17, 161.72, 154.88, 142.07(d, J=6.9 Hz), 130.07(d, J=8.3 Hz), 129.99, 129.37, 124.76, 124.12(d, J=2.8 Hz), 120.89, 117.58, 115.63, 115.41, 114.56, 114.35, 49.70, 26.36, 14.12
3u	7.39—7.35(m, 2H), 7.22(td, J=8.1, 1.6 Hz, 1H), 7.17(s, 1H), 7.05—6.98(m, 3H), 6.93(dd, J =8.0, 0.8 Hz, 1H), 6.87(td, J=7.5, 1.0 Hz, 1H), 5.36(s, 1H), 2.47(qd, J=7.4, 2.7 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	162.04(d, J=245 Hz), 155.05, 134.99(d, J=3 Hz), 130.12, 130.03(d, J=2.6 Hz), 129.32, 124.87, 120.80, 117.69, 115.59, 115.38, 49.78, 26.35, 14.10
Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3v	7.40—7.25(m, 6H), 7.16(dd, J=8.6, 2.6 Hz, 1H), 7.03(d, J=2.5 Hz, 1H), 6.86(d, J=8.6 Hz, 1H), 5.31(s, 1H), 2.49(dd, J=13.7, 7.0 Hz, 2H), 1.26(t, J=7.4 Hz, 3H)	153.82, 138.45, 129.70, 129.03, 128.80, 128.76, 128.41, 128.36, 128.32, 127.82, 126.81, 125.44, 119.00, 50.32, 29.71, 26.41, 14.10
3w	7.64(s, 1H), 7.18—7.14(m, 1H), 6.96(dd, J=7.5, 1.3 Hz, 1H), 6.86(d, J=7.7, 1H), 6.80(dd, J=11.5, 4.1 Hz, 1H), 3.78(d, J=9.1 Hz, 1H), 2.29(qd, J=7.4, 1.5 Hz, 2H), 2.14(d, J=12.8 Hz, 1H), 1.87—1.85(m, 1H), 1.74(dd, J=10.4, 2.7 Hz, 1H), 1.63—1.60(m, 2H), 1.41(d, J=13.0 Hz, 1H), 1.23(ddd, J=15.7, 8.6, 5.2 Hz, 1H), 1.15—1.03(m, 6H), 0.92—0.90(m, 1H)	155.51, 131.14, 128.68, 124.72, 119.88, 117.59, 55.16, 41.45, 32.07, 32.02, 26.28, 26.16, 14.24
3x	7.20(t, J=7.5 Hz, 1H), 7.08(d, J=7.2 Hz, 1H), 6.97—6.79(m, 2H), 6.75(s, 1H), 3.82(s, 2H), 2.42(q, J=7.3 Hz, 2H), 1.26—1.21(m, 3H)	155.51, 130.45, 129.11, 122.44, 120.52, 117.20, 32.38 , 24.76, 14.23
4a	7.40(d, J=7.4 Hz, 2H), 7.25(td, J=17.2, 7.3 Hz, 5H), 6.74(d, J=8.5 Hz, 2H), 5.79(s, 1H), 5.12(s, 1H), 2.37(q, J=7.4 Hz, 2H), 1.19(t, J=7.4 Hz, 3H)	154.72, 141.81, 133.61, 129.56, 128.56, 128.26, 127.09, 115.49, 53.17, 26.27, 14.25

Table 3 1H NMR and 13C NMR data for compounds 3a—3x and 4a

Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3a	7.40(d, J=7.4 Hz, 2H), 7.32—7.16(m, 5H), 7.05(dd, J=7.6, 1.2 Hz, 1H), 6.91(dd, J=8.0, 0.7 Hz, 1H), 6.88—6.82(m, 1H), 5.39(s, 1H), 2.49—2.43(m, 2H), 1.23(t, J=7.4 Hz, 3H)	155.15, 139.31, 130.17, 129.21, 128.69, 128.67, 128.53, 128.51, 127.55, 125.16, 120.76, 117.60, 50.47, 26.36, 14.20
3b	7.40(d, J=7.4 Hz, 2H), 7.34—7.29(m, 2H), 7.21(ddd, J=15.4, 10.6, 4.4 Hz, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.95—6.89(m, 1H), 6.84(td, J=7.6, 1.0 Hz, 1H), 5.35(s, 1H), 2.48—2.39(m, 2H), 1.61(dd, J=14.6, 7.3 Hz, 2H), 0.95(t, J=7.4 Hz, 3H)	155.22, 139.30, 130.18, 129.21, 128.66, 128.48, 127.53, 125.11, 120.70, 117.64, 50.97, 34.33, 22.32, 13.49
3c	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=10.0, 4.8 Hz, 3H), 7.26—7.11(m, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.97—6.90(m, 1H), 6.88—6.82(m, 1H), 5.35(s, 1H), 2.49—2.42(m, 2H), 1.63—1.51(m, 2H), 1.38—1.33(m, 2H), 0.85(t, J=7.3 Hz, 3H)	155.23, 139.29, 130.19, 129.21, 128.67, 128.51, 128.49, 128.46, 127.54, 125.11, 120.71, 117.64, 51.04, 32.02, 21.01, 21.96, 13.64
3d	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=9.7, 5.1 Hz, 3H), 7.28—7.13(m, 2H), 7.03(dd, J=7.6, 1.1 Hz, 1H), 6.96—6.88(m, 1H), 6.84(t, J=7.5 Hz, 1H), 5.35(s, 1H), 2.45(tq, J=10.7, 5.3 Hz, 2H), 1.57(dd, J=14.7, 7.3 Hz, 2H), 1.31—1.26(m, 4H), 0.85(t, J=7.1 Hz, 3H)	155.23, 139.31, 130.19, 129.21, 128.67, 128.51, 128.48, 128.46, 127.53, 125.12, 120.71, 117.63, 51.05, 32.33, 30.99, 28.61, 22.23, 13.94
3e	7.40(d, J=7.5 Hz, 2H), 7.31(dd, J=9.9, 4.9 Hz, 3H), 7.27—7.17(m, 2H), 7.03(dd, J=7.6, 1.2 Hz, 1H), 6.92(dd, J=8.0, 0.6 Hz, 1H), 6.86—6.82(m, 1H), 5.34(s, 1H), 2.45(tq, J=10.8, 5.3 Hz, 2H), 1.60—1.56(m, 2H), 1.32—1.23(m, 8H), 0.86(t, J=6.9 Hz, 3H)	155.25, 139.29, 130.18, 129.21, 128.66, 128.54, 128.49, 127.53, 125.09, 120.70, 117.65, 51.08, 32.34, 31.67, 28.92, 28.80, 28.77, 22.61, 14.09
3f	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=13.8, 6.6 Hz, 3H), 7.21(ddd, J=11.3, 8.7, 4.4 Hz, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.92(dd, J= 8.0, 0.6 Hz, 1H), 6.87—6.80(m, 1H), 5.31(s, 1H), 2.35(qd, J=12.5, 6.8 Hz, 2H), 1.83(dt, J=13.4, 6.7 Hz, 1H), 0.95(dd, J=8.0, 6.8 Hz, 6H)	155.26, 139.36, 130.24, 129.22, 128.66, 128.51, 128.48, 128.45, 127.54, 125.12, 120.69, 117.65, 51.54, 41.27, 28.24, 22.22, 21.98
3g	7.40(d, J=7.4 Hz, 2H), 7.36—7.26(m, 3H), 7.21(ddd, J=17.1, 11.2, 4.3 Hz, 2H), 7.03(dd, J=7.6, 1.1 Hz, 1H), 6.92(d, J=7.7 Hz, 1H), 6.84(t, J=7.5 Hz, 1H), 5.35(s, 1H), 2.48—2.43(m, 2H), 1.61(dt, J=13.3, 6.6 Hz, 1H), 1.50—1.45(m, 2H), 0.84—0.81(m, 6H)	155.22, 139.26, 130.19, 129.23, 128.66, 128.51, 128.49, 128.46, 127.54, 125.06, 120.71, 117.64, 51.03, 37.92, 30.36, 27.40, 22.32, 22.15
3h	7.49—7.34(m, 3H), 7.30(t, J=7.4 Hz, 2H), 7.26—7.14(m, 2H), 7.04(dd, J=7.6, 1.2 Hz, 1H), 6.92(d, J=8.0 Hz, 1H), 6.84(t, J=7.5 Hz, 1H), 5.41(s, 1H), 2.77(dt, J=13.4, 6.7 Hz, 1H), 1.29—1.24(m, 6H)	155.30, 139.28, 130.09, 129.19, 128.67, 128.48, 127.50, 125.11, 120.73, 117.73, 50.13, 35.76, 23.07, 22.85
Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3i	7.40(d, J=7.3 Hz, 3H), 7.30(t, J=7.4 Hz, 2H), 7.26—7.13(m, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.97—6.88(m, 1H), 6.85(dd, J=10.8, 4.1 Hz, 1H), 5.36(s, 1H), 2.91(p, J=7.0 Hz, 1H), 1.91(dt, J=12.3, 6.3 Hz, 2H), 1.72—1.70(m, 2H), 1.64—1.50(m, 4H)	155.33, 139.37, 130.05, 129.15, 128.64, 128.46, 128.44, 127.47, 125.36, 120.70, 117.71, 51.40, 44.23, 33.65, 33.20, 24.88, 24.74
3j	7.36(d, J=7.3 Hz, 2H), 7.30(t, J=7.3 Hz, 4H), 7.27—7.22(m, 2H), 7.18(dd, J=12.7, 4.5 Hz, 3H), 6.95(dd, J=7.7, 1.3 Hz, 1H), 6.90(d, J= 8.4 Hz, 2H), 6.86—6.79(m, 1H), 5.11(s, 1H), 3.59(d, J=3.2 Hz, 2H)	155.03, 138.75, 137.28, 130.31 , 129.30, 129.01, 128.99, 128.76, 128.73, 127.65, 127.47, 124.86, 120.80, 117.60, 49.68, 36.54
3k	7.34(dt, J=14.9, 7.8 Hz, 6H), 7.27—7.19(m, 2H), 7.15(d, J=8.2 Hz, 2H), 6.99(s, 1H), 6.96—6.90(m, 2H), 6.88—6.79(m, 1H), 5.14(s, 1H), 3.59(d, J=2.5 Hz, 2H), 1.32(s, 9H)	155.14, 150.39, 138.73, 134.04, 130.35, 129.27, 128.73, 128.67, 128.64, 127.59, 125.59, 124.78, 120.70, 117.64, 49.97, 36.13, 34.57, 31.37
3l	7.36—7.18(m, 8H), 7.11(d, J=8.4 Hz, 2H), 6.99(dd, J=7.6, 1.3 Hz, 1H), 6.93—6.81(m, 2H), 6.78(s, 1H), 5.12(s, 1H), 3.56(s, 2H)	154.87, 138.61, 135.81, 133.18, 130.32, 130.29, 129.35,128.81, 128.75, 128.64, 127.70, 124.63, 120.88, 117.52, 49.65, 35.89
3m	7.40—7.29(m, 4H), 7.26—7.17(m, 2H), 7.13—7.08(m, 4H), 6.96(s, 1H), 6.93—6.90(m, 2H), 6.83(t, J=7.4 Hz, 1H), 5.09(s, 1H), 3.56(d, J=5.1 Hz, 2H), 2.33(s, 3H)	155.08, 138.74, 137.14, 134.11, 130.31, 129.41, 129.26 , 128.90, 128.79, 128.71, 127.61, 124.87, 120.74, 117.62, 49.64, 36.21, 21.20
3n	7.61(s, 1H), 7.42(d, J=7.4 Hz, 2H), 7.34(t, J=7.4 Hz, 2H), 7.30—7.21(m, 2H), 6.74(dd, J=7.2, 5.3 Hz, 2H), 5.35(s, 1H), 2.46(q, J=7.4 Hz, 2H), 1.44(s, 9H), 1.25(t, J=7.3 Hz, 3H)	154.38, 138.88, 138.29, 128.82, 128.63, 128.04, 127.56, 126.66, 125.19, 119.80, 77.36, 77.05, 76.73, 51.54, 34.93, 29.76, 26.27, 14.24
3o	7.47(d, J=7.4 Hz, 2H), 7.28(t, J=7.5 Hz, 2H), 7.22—7.08(m, 2H), 6.81(t, J=8.0 Hz, 1H), 6.71(dd, J=8.0, 1.1 Hz, 1H), 5.98(s, 1H), 5.66(s, 1H), 4.10—4.02(m, 2H), 2.44(q, J=7.4 Hz, 2H), 1.41(t, J=7.0 Hz, 3H), 1.23(t, J=7.4 Hz, 3H)	145.71, 143.18, 141.48, 128.38, 128.35, 127.33, 126.88, 121.02, 119.63, 110.09, 64.57, 46.17, 26.31, 14.92, 14.31
3p	7.40(d, J=7.5 Hz, 2H), 7.31(t, J=7.4 Hz, 2H), 7.26—7.22(m, 1H), 7.12(s, 1H), 7.00(dd, J=8.2, 1.7 Hz, 1H), 6.83(dd, J=8.1, 4.9 Hz, 2H), 5.34(s, 1H), 2.48(dd, J=7.4, 4.0 Hz, 2H), 2.21(s, 3H), 1.25(t, J=7.4 Hz, 3H)	152.92, 139.33, 130.56, 129.85, 129.72, 128.65, 128.45, 127.48, 124.56, 117.49, 50.76, 26.36, 20.57, 14.16
3q	7.41(d, J=7.4 Hz, 2H), 7.32(dd, J=10.1, 4.7 Hz, 2H), 7.25(t, J=7.2 Hz, 1H), 6.86(d, J=8.8 Hz, 1H), 6.76(dd, J=8.8, 3.1 Hz, 2H), 6.63(d, J=3.0 Hz, 1H), 5.34(s, 1H), 3.70(s, 3H), 2.48(qd, J=7.4, 2.0 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	153.54, 148.85, 139.05, 128.66, 128.64, 128.49, 128.44, 127.56, 126.25, 118.26, 115.74, 113.95, 55.66, 50.59, 26.35, 14.18
3r	7.54—7.51(m, 1H), 7.29(s, 1H), 7.23—7.11(m, 4H), 6.94(ddd, J=11.9, 7.9, 1.0 Hz, 2H), 6.83—6.80(m, 1H), 5.52(s, 1H), 2.51(q, J=7.4 Hz, 2H), 2.39(s, 3H), 1.27(t, J=7.4 Hz, 3H)	155.18, 137.18, 136.28, 130.73, 129.94, 128.98, 128.62, 127.48, 126.47, 125.15, 120.79, 117.44, 46.90, 26.47, 19.31, 14.16
3s	7.34(d, J=8.5 Hz, 2H), 7.22(ddd, J=11.3, 8.7 Hz, 4.7 Hz, 2H), 7.08—7.03(m, 2H), 6.93—6.85(m, 2H), 5.36(s, 1H), 2.47(qd, J=7.4, 2.0 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	154.95, 137.91, 133.29, 129.97, 129.84, 129.35, 128.78, 124.75, 120.86, 117.63, 49.68, 26.37, 14.12
3t	7.30—7.26(m, 1H), 7.21(ddd, J=12.9, 9.8, 4.7 Hz, 2H), 7.14(dd, J=10.1, 2.0 Hz, 1H), 7.06(dd, J=7.6, 1.3 Hz, 1H), 7.01(s, 1H), 6.97—6.86(m, 3H), 5.38(s, 1H), 2.49(qd, J=7.4, 1.6 Hz, 2H), 1.26(t, J=7.4 Hz, 3H)	164.17, 161.72, 154.88, 142.07(d, J=6.9 Hz), 130.07(d, J=8.3 Hz), 129.99, 129.37, 124.76, 124.12(d, J=2.8 Hz), 120.89, 117.58, 115.63, 115.41, 114.56, 114.35, 49.70, 26.36, 14.12
3u	7.39—7.35(m, 2H), 7.22(td, J=8.1, 1.6 Hz, 1H), 7.17(s, 1H), 7.05—6.98(m, 3H), 6.93(dd, J =8.0, 0.8 Hz, 1H), 6.87(td, J=7.5, 1.0 Hz, 1H), 5.36(s, 1H), 2.47(qd, J=7.4, 2.7 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	162.04(d, J=245 Hz), 155.05, 134.99(d, J=3 Hz), 130.12, 130.03(d, J=2.6 Hz), 129.32, 124.87, 120.80, 117.69, 115.59, 115.38, 49.78, 26.35, 14.10
Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3v	7.40—7.25(m, 6H), 7.16(dd, J=8.6, 2.6 Hz, 1H), 7.03(d, J=2.5 Hz, 1H), 6.86(d, J=8.6 Hz, 1H), 5.31(s, 1H), 2.49(dd, J=13.7, 7.0 Hz, 2H), 1.26(t, J=7.4 Hz, 3H)	153.82, 138.45, 129.70, 129.03, 128.80, 128.76, 128.41, 128.36, 128.32, 127.82, 126.81, 125.44, 119.00, 50.32, 29.71, 26.41, 14.10
3w	7.64(s, 1H), 7.18—7.14(m, 1H), 6.96(dd, J=7.5, 1.3 Hz, 1H), 6.86(d, J=7.7, 1H), 6.80(dd, J=11.5, 4.1 Hz, 1H), 3.78(d, J=9.1 Hz, 1H), 2.29(qd, J=7.4, 1.5 Hz, 2H), 2.14(d, J=12.8 Hz, 1H), 1.87—1.85(m, 1H), 1.74(dd, J=10.4, 2.7 Hz, 1H), 1.63—1.60(m, 2H), 1.41(d, J=13.0 Hz, 1H), 1.23(ddd, J=15.7, 8.6, 5.2 Hz, 1H), 1.15—1.03(m, 6H), 0.92—0.90(m, 1H)	155.51, 131.14, 128.68, 124.72, 119.88, 117.59, 55.16, 41.45, 32.07, 32.02, 26.28, 26.16, 14.24
3x	7.20(t, J=7.5 Hz, 1H), 7.08(d, J=7.2 Hz, 1H), 6.97—6.79(m, 2H), 6.75(s, 1H), 3.82(s, 2H), 2.42(q, J=7.3 Hz, 2H), 1.26—1.21(m, 3H)	155.51, 130.45, 129.11, 122.44, 120.52, 117.20, 32.38 , 24.76, 14.23
4a	7.40(d, J=7.4 Hz, 2H), 7.25(td, J=17.2, 7.3 Hz, 5H), 6.74(d, J=8.5 Hz, 2H), 5.79(s, 1H), 5.12(s, 1H), 2.37(q, J=7.4 Hz, 2H), 1.19(t, J=7.4 Hz, 3H)	154.72, 141.81, 133.61, 129.56, 128.56, 128.26, 127.09, 115.49, 53.17, 26.27, 14.25

Scheme 2 Proposed reaction mechanism

Scheme 3 Reaction of 4-[hydroxy(phenyl)methyl]-phenol with CH3CH2SH

参考文献 45

[1]	Kondo T., Mitsudo T. A., Chem.Rev., 2000, 100(8), 3205—3220
[2]	Feng M., Tang B., Liang S. H., Jiang X., Curr. Top. Med.Chem.,2016, 16(17), 1200—1216
[3]	Ilardi E. A., Vitaku E., Najardarson J. T., J. Med.Chem., 2014, 57(7), 2832—2842
[4]	Smith B. R., Eastman C. M., Nijardarson., J. Med.Chem., 2014, 57(23), 9764—9773
[5]	Wei Y. Z., Tan X. Z., Chem. Res. Chinese Universities,2017, 33(5), 731—735
[6]	Zhong S. M., Zheng M., Pu S. X., Xing Y. B., Li K. Z., Wang H., Chem. Res. Chinese Universities,2017, 33(6), 979—985
[7]	Cinar M. E., Ozturk T., Chem.Rev., 2015, 115(9), 3036—3140
[8]	Takimiya K., Osaka I., Mori T., Nakano M., Acc. Chem.Res., 2014, 47(5), 1493—1502
[9]	Scott K. A., Njardarson J. T., Top. Curr.Chem., 2018, 376, 5—38
[10]	Hammond M. L., Zambias R. A., Chang M. N., Jensen N. P., McDonald J., Thompson K., Boulton D. A., Kopka I. K., Hand K. M., Opas E. E., Luell S., Bach T., Davies P., MacIntyre D. E., Bonney R. J., Humes J. L., J. Med.Chem.,1990, 33(3), 908—918
[11]	Katritzky A. R., Zhang Z., Lan X., Lang H., J. Org.Chem., 1994, 59(7), 1900—1903
[12]	Modica E., Zanaletti R., Freccero M., Mella M., J. Org.Chem.,2001, 66(1), 41—52
[13]	Shaikh A. K., Cobb A. J. A., Varvounis G., Org.Lett., 2012, 14(2), 584—587
[14]	Lau C. K., Williams H. W. R., Tardiff S., Dufresne C., Scheigetz J., Belanger P., Can. J.Chem., 1989, 67, 1384—1387
[15]	Guo W., Wu B., Zhou X., Chen P., Wang X., Zhou Y. G., Liu Y., Li C., Angew. Chem. Int.Ed., 2015, 54(15), 4522—4526
[16]	Guo W., Wu B., Zhou X., Chen P., Wang X., Zhou Y. G., Liu Y., Li C.,Angew. Chem. Int.Ed., 2015, 54(15), 4605—4609
[17]	Lai Z., Sun J., Synlett.,2016, 27(4), 555—558
[18]	Pathak T. P., Sigman M. S., J. Org.Chem.,2011, 76(22), 9210—9215
[19]	Will N. J., Bray C. D., Chem. Eur.J.,2012, 18(30), 9160—9173
[20]	Caruana L., Fochi M., Bernardi L., Molecules,2015, 20(7), 11733—11764
[21]	Wang Z., Sun J., Synthesis,2015, 47(23), 3629—3644
[22]	Water R. W. V. D., Pettus T. R. R., Tetrahedron,2002, 58(27), 5367—5405
[23]	Kulikov A., Arumugam S., Popik V. V., J. Org.Chem.,2008, 73(19), 7611—7615
[24]	Mattson A. E., Scheidt K. A., J. Am. Chem.Soc.,2007, 129(15), 4508—4509
[25]	Luan Y., Schaus S. E., J. Am. Chem.Soc., 2012, 134(49), 19965—19968
[26]	Chen M. W., Gao L. L., Ye Z. S., Jiang G. F., Zhou Y. G., Chem.Commun.,2013, 49, 1660—1662
[27]	Bai W. J., David J. G., Feng Z. G., Weaver M. G., Wu K. L., Pettus T. R. R., Acc. Chem.Res., 2014, 47(12), 3655—3664
[28]	Zhao W., Wang Z., Chu B., Sun J., Angew. Chem. Int.Ed., 2015, 54(6), 1910—1913
[29]	Huang Y., Hayashi T., J. Am. Chem.Soc.,2015, 137(24), 7556—7559
[30]	Wan Z., Ai F., Wang Z., Zhao W., Zhu G., Lin Z., Sun J., J. Am. Chem.Soc., 2015, 137(1), 383—389
[31]	Wu B., Yu Z., Gao X., Lan Y., Zhou Y. G., Angew. Chem. Int.Ed.,2017, 56(14), 4006—4010
[32]	Chen P., Wang K., Guo W., Liu X., Liu Y., Li C., Angew. Chem. Int.Ed.,2017, 56(13), 3689—3693
[33]	Nising C. F., Brase S., Chem. Soc.Rev., 2008, 37, 1218—1228
[34]	Nising C. F., Brase S., Chem. Soc.Rev., 2012, 41, 988—999
[35]	Heravi M. M., Hajiabbasi P., Mol.Diversity,2014, 18(2), 411—439
[36]	Thirupathi N., Tung C. H., Xu Z. H.,Adv. Synth.Catal., 2018, 360(18), 3585—3589
[37]	Corma A., Gonzalez-Arellano C., Iglesias M., Sanchez F., App. Catal. A:Gen.,2010, 375(1), 49—54
[38]	Lee W. Z., Tseng H. S., Wang T. L., Tsai H. L., Kuo T. S.,Organometallics,2010, 29(13), 2874—2881
[39]	Badoiu A., Bernardinelli G., Besnard C., Kundig E. P., Org. Biomol.Chem., 2010, 8, 193—200
[40]	O’Byrne A., Murray C., Keegan D., Palacio C., Evans P., Morgan B. S., Org. Biomol.Chem., 2010, 8, 539—545
[41]	Firouzabadi H., Iranpoor N., Abbasi M., Adv. Synth.Catal., 2009, 351, 755—766
[42]	Rajabi F., Razavi S., Luque R., Green Chem.,2010, 12, 786—789
[43]	Inoue T., Inoue S., Sato K., Bull. Chem. Soc.Jpn.,1990, 63(4), 1062—1068
[44]	Lanzi M., Merad J., Boyarskaya D V., Maestri G., Allain C., Masson Géraldine., Org.Lett., 2018, 20(17), 5247—5250
[45]	Basha R. S., Chen C. W., Reddy D. M., Lee C. F., Chem-Asian J.,2018,13(17), 2475—2483

Sc(Ⅲ)催化硫醇对邻亚甲基苯醌的亲核加成反应合成邻羟基苄硫醚衍生物

Sc(Ⅲ) Catalyzed Nucleophilic Addition of in situ Generated ortho-Quinone Methides with Thiols: an Efficient Access to ortho-Hydroxybenzyl Thioethers^†

RichHTML

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

图/表 6

参考文献 45

相关文章 15

编辑推荐

Metrics

本文评价

[1]	李艾橘, 王玉玺, 卢少勇, 刘堃. 硫醇末端基聚合物对金纳米粒子配体置换[J]. 高等学校化学学报, 2018, 39(3): 552.
[2]	于海丰, 廖沛球. 肟的无气味硫缩醛/酮化反应[J]. 高等学校化学学报, 2012, 33(09): 1969.
[3]	曾智关绍巍祝世洋代中明姜振华. 新型芳基硫醇的合成及在聚芳醚砜紫外交联中的应用[J]. 高等学校化学学报, 2011, 32(2): 407.
[4]	谢斌, 张秀兰, 邹立科, 王军, 赖川, 吴宇, 冯建申. 配合物{[Cu(hmtade)][Ni(dmit)₂]}₂·4DMSO的合成、表征及晶体结构[J]. 高等学校化学学报, 2009, 30(12): 2337.
[5]	刘艳芝, 施小宁, 李志锋, 唐慧安, 袁焜, 张俊彦. CH₃SH…HOO开壳型氢键复合物的结构及其电子密度拓扑性质[J]. 高等学校化学学报, 2009, 30(10): 2049.
[6]	祝纶宇,许凯,王洪,刘鹏,陈德宏,艾好,陈鸣才 . 稀土(镧)硫醇盐的合成与表征[J]. 高等学校化学学报, 2008, 29(9): 1786.
[7]	张晓鹏,陆世维 . 硒作用下苯胺和硫醇羰基化合成硫代氨基甲酸酯[J]. 高等学校化学学报, 2008, 29(6): 1137.
[8]	于海丰,王艳茹,欧阳艳,王岩,刘群 . 4,4-二乙硫／苄硫基-3-烯-2-丁酮的合成及其作为无气味硫醇替代试剂的缩硫醛/酮化反应[J]. 高等学校化学学报, 2006, 27(12): 2300.
[9]	欧阳艳, 于海丰, 董德文, 刘军, 王芒, 刘群. 2-(1,3-亚丙二硫)亚甲基-3-羰基丁酸作为硫醇替代试剂在缩硫醛/酮化反应中的应用[J]. 高等学校化学学报, 2005, 26(12): 2237.
[10]	欧阳艳于海丰董德文刘军王芒刘群. 2-(1,3-亚丙二硫)亚甲基-3-羰基丁酸作为硫醇替代试剂在缩硫醛/酮化反应中的应用[J]. 高等学校化学学报, 2005, 26(12): 2237.
[11]	龚少云, 沈艳飞, 周伟红, 李景虹. 硫醇自组装膜对金电极上吡咯电化学聚合的影响[J]. 高等学校化学学报, 2004, 25(9): 1719.
[12]	刘福胜, 于世涛, 葛晓萍, 杨锦宗. 2位取代嘌呤衍生物的合成研究[J]. 高等学校化学学报, 2003, 24(9): 1592.
[13]	刘建兵, 赵国锋, 李焜昶, 金桂玉. 1-(2,4-二氯苯基)-1-氨基-4,4-二甲基-2-(1,2,4-三唑-1-基)-3-戊酮(醇)的合成及生物活性研究[J]. 高等学校化学学报, 2001, 22(S1): 92.
[14]	陈文彬, 金桂玉. 新型含硫三唑类化合物的合成及生物活性研究[J]. 高等学校化学学报, 2001, 22(7): 1147.
[15]	杨生荣, 任嗣利, 张俊彦, 张绪寿. 自组装单分子膜的结构及其自组装机理[J]. 高等学校化学学报, 2001, 22(3): 470.

Sc(Ⅲ)催化硫醇对邻亚甲基苯醌的亲核加成反应合成邻羟基苄硫醚衍生物

Sc(Ⅲ) Catalyzed Nucleophilic Addition of in situ Generated ortho-Quinone Methides with Thiols: an Efficient Access to ortho-Hydroxybenzyl Thioethers†

RichHTML

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

图/表 6

参考文献 45

相关文章 15

编辑推荐

Metrics

本文评价

Sc(Ⅲ) Catalyzed Nucleophilic Addition of in situ Generated ortho-Quinone Methides with Thiols: an Efficient Access to ortho-Hydroxybenzyl Thioethers^†