 
	 
	高等学校化学学报 ›› 2025, Vol. 46 ›› Issue (10): 20250202.doi: 10.7503/cjcu20250202
收稿日期:2025-07-19
									
				
									
				
									
				
																出版日期:2025-10-10
														
				
											发布日期:2025-08-29
									
			通讯作者:
					曹佳
											E-mail:jcao@yau.edu.cn
												基金资助:
        
               		JI Baobao, WANG Zhixiang, LIU Yan, CAO Jia( )
)
			  
			
			
			
                
        
    
Received:2025-07-19
									
				
									
				
									
				
																Online:2025-10-10
														
				
											Published:2025-08-29
									
			Contact:
					CAO Jia   
											E-mail:jcao@yau.edu.cn
												Supported by:摘要:
硅硼化物作为硅自由基前体在有机合成中备受关注, 已成为研究热点. 本文发展了在可见光催化下实现硅硼化物和酰基氮 盐对烯烃的三组分双官能化反应, 合成了一系列高附加值含硅的酮化物. 通过机理实验和理论计算研究发现, 光催化下碱/硅基硼酸酯络合物与酰基氮
盐对烯烃的三组分双官能化反应, 合成了一系列高附加值含硅的酮化物. 通过机理实验和理论计算研究发现, 光催化下碱/硅基硼酸酯络合物与酰基氮 盐进行单电子转移, 继而产生的硅基自由基和酰基
盐进行单电子转移, 继而产生的硅基自由基和酰基 盐自由基阴离子依次与烯烃偶联, 最终生成在β位有硅烷基的酮类化合物. 该方法具有良好的官能团耐受性、 温和的反应条件和广泛的底物适用范围.
盐自由基阴离子依次与烯烃偶联, 最终生成在β位有硅烷基的酮类化合物. 该方法具有良好的官能团耐受性、 温和的反应条件和广泛的底物适用范围.
中图分类号:
TrendMD:
姬宝宝, 王智香, 刘艳, 曹佳. 可见光催化烯烃的硅酰基化反应. 高等学校化学学报, 2025, 46(10): 20250202.
JI Baobao, WANG Zhixiang, LIU Yan, CAO Jia. Visible-light Photocatalytic Silylacylation of Alkenes. Chem. J. Chinese Universities, 2025, 46(10): 20250202.
| Compd. | Appearance | Yield(%) | HRMS, m/z[M+H]+ (calcd.) | Compd. | Appearance | Yield(%) | HRMS, m/z[M+H]+ (calcd.) | 
|---|---|---|---|---|---|---|---|
| c1 | Colorless oil liquid | 83 | 395.1801(395.1802) b | c19 | Colorless oil liquid | 40 | 411.1537(411.1541) c | 
| c2 | Colorless oil liquid | 70 | 359.1827(359.1826) | c20 | Colorless oil liquid | 32 | 427.1715(427.1700) | 
| c3 | Colorless oil liquid | 76 | 399.1550(399.1551) b | c21 | Colorless oil liquid | 90 | 360.1768(360.1778) | 
| c4 | Colorless oil liquid | 66 | 415.1254(415.1255) b | c22 | Colorless oil liquid | 18 | 395.1804(395.1802) b | 
| c5 | Colorless oil liquid | 61 | 439.1700(439.1700) b | c24 | Colorless oil liquid | 63 | 376.2189(376.2091) d | 
| c6 | Colorless oil liquid | 78 | 431.2039(431.2037) | c25 | Colorless oil liquid | 61 | 394.2000(394.1997) d | 
| c7 | Colorless oil liquid | 45 | 427.1704(427.1700) | c26 | Colorless oil liquid | 42 | 390.2254(390.2248) d | 
| c8 | Colorless oil liquid | 52 | 431.2222(431.2221) | c27 | Colorless oil liquid | 67 | 406.2201(406.2197) d | 
| c9 | Colorless oil liquid | 51 | 389.1932(389.1931) | c28 | Colorless oil liquid | 55 | 432. 2719(432.2717) d | 
| c10 | Colorless oil liquid | 47 | 437.2270(437.2271) b | c29 | Colorless oil liquid | 48 | 443.1650(443.1649) | 
| c11 | Colorless oil liquid | 78 | 431.0997(431.0995) c | c30 | Colorless oil liquid | 68 | 417.1882(417.1880) | 
| c12 | Colorless oil liquid | 58 | 427.1489(427.1490) c | c31 | Colorless oil liquid | 47 | 427.1704(427.1700) | 
| c13 | Colorless oil liquid | 43 | 427.1703(427.1700) | c32 | Colorless oil liquid | 54 | 397.1998(394.1997) d | 
| c14 | Colorless oil liquid | 45 | 417.1884(417.1880) | c33 | Colorless oil liquid | 45 | 390.2245(390.2248) d | 
| c15 | Colorless oil liquid | 69 | 415.1287(415.1290) c | c35 | Colorless oil liquid | 35 | 541.3132(541.3134) | 
| c16 | Colorless oil liquid | 52 | 389.1934(389.1931) | c36 | Colorless oil liquid | 37 | 591.3265(591.3264) b | 
| c17 | Colorless oil liquid | 37 | 473.1697(473.1698) c | c40 | Colorless oil liquid | 60 | 475.2451(475.2452) | 
| c18 | Colorless oil liquid | 53 | 431.0996(431.0995) c | 
Table 1 Appearance, yields and HRMS data of target compounds c1—c40 a
| Compd. | Appearance | Yield(%) | HRMS, m/z[M+H]+ (calcd.) | Compd. | Appearance | Yield(%) | HRMS, m/z[M+H]+ (calcd.) | 
|---|---|---|---|---|---|---|---|
| c1 | Colorless oil liquid | 83 | 395.1801(395.1802) b | c19 | Colorless oil liquid | 40 | 411.1537(411.1541) c | 
| c2 | Colorless oil liquid | 70 | 359.1827(359.1826) | c20 | Colorless oil liquid | 32 | 427.1715(427.1700) | 
| c3 | Colorless oil liquid | 76 | 399.1550(399.1551) b | c21 | Colorless oil liquid | 90 | 360.1768(360.1778) | 
| c4 | Colorless oil liquid | 66 | 415.1254(415.1255) b | c22 | Colorless oil liquid | 18 | 395.1804(395.1802) b | 
| c5 | Colorless oil liquid | 61 | 439.1700(439.1700) b | c24 | Colorless oil liquid | 63 | 376.2189(376.2091) d | 
| c6 | Colorless oil liquid | 78 | 431.2039(431.2037) | c25 | Colorless oil liquid | 61 | 394.2000(394.1997) d | 
| c7 | Colorless oil liquid | 45 | 427.1704(427.1700) | c26 | Colorless oil liquid | 42 | 390.2254(390.2248) d | 
| c8 | Colorless oil liquid | 52 | 431.2222(431.2221) | c27 | Colorless oil liquid | 67 | 406.2201(406.2197) d | 
| c9 | Colorless oil liquid | 51 | 389.1932(389.1931) | c28 | Colorless oil liquid | 55 | 432. 2719(432.2717) d | 
| c10 | Colorless oil liquid | 47 | 437.2270(437.2271) b | c29 | Colorless oil liquid | 48 | 443.1650(443.1649) | 
| c11 | Colorless oil liquid | 78 | 431.0997(431.0995) c | c30 | Colorless oil liquid | 68 | 417.1882(417.1880) | 
| c12 | Colorless oil liquid | 58 | 427.1489(427.1490) c | c31 | Colorless oil liquid | 47 | 427.1704(427.1700) | 
| c13 | Colorless oil liquid | 43 | 427.1703(427.1700) | c32 | Colorless oil liquid | 54 | 397.1998(394.1997) d | 
| c14 | Colorless oil liquid | 45 | 417.1884(417.1880) | c33 | Colorless oil liquid | 45 | 390.2245(390.2248) d | 
| c15 | Colorless oil liquid | 69 | 415.1287(415.1290) c | c35 | Colorless oil liquid | 35 | 541.3132(541.3134) | 
| c16 | Colorless oil liquid | 52 | 389.1934(389.1931) | c36 | Colorless oil liquid | 37 | 591.3265(591.3264) b | 
| c17 | Colorless oil liquid | 37 | 473.1697(473.1698) c | c40 | Colorless oil liquid | 60 | 475.2451(475.2452) | 
| c18 | Colorless oil liquid | 53 | 431.0996(431.0995) c | 
| Compd. | 1H NMR(400 M Hz, CDCl3), δ | 13C NMR(101 M Hz, CDCl3), δ | |
|---|---|---|---|
| c1 | 7.40—7.34(m, 2H), 7.28—7.22(m, 3H), 7.18—7.12(m, 2H), 6.99(d, J=7.4 Hz, 2H), 6.91—6.85(m, 4H), 4.26(t, J=7.5 Hz, 1H), 2.16(s, 3H), 2.10(s, 3H), 1.66 (m, 1H), 1.32(m, 1H), 0.06(s, 3H), 0.04(s, 3H) | 204.5, 138.8, 138.8, 137.8, 137.2, 136.6, 133.8, 131.5, 130.6, 129.4, 129.0, 128.4, 127.9, 127.5, 125.3, 52.2, 21.1, 20.6, 19.8, -2.2, -2.5 | |
| c2 | 7.53—7.48(m, 2H), 7.42—7.36(m, 3H), 7.31(d, J=7.8 Hz, 1H), 7.28—7.25(m, 1H), 7.24—7.21(m, 2H), 7.19—7.14(m, 3H), 7.12(d, J=7.8 Hz, 2H), 4.43(t, J =7.6 Hz, 1H), 2.23(s, 3H), 1.85—1.77(m, 1H), 1.52—1.44(m, 1H), 0.18(d, J =11.4 Hz, 6H) | 204.4, 140.2, 138.8, 138.6, 137.8, 133.7, 131.5, 130.6, 129.1, 128.7, 128.6, 127.9, 127.4, 127.0, 125.3, 52.6, 20.6, 19.9, -2.2, -2.5 | |
| c3 | 7.50—7.43(m, 2H), 7.42—7.35(m, 3H), 7.30—7.24(m, 2H), 7.17—7.07(m, 4H), 6.95—6.86(m, 2H), 4.40(t, J=8.0 Hz, 1H), 2.24(s, 3H), 1.82—1.69(m, 1H), 1.51—1.40(m, 1H), 0.17(s, 6H) | 204.3, 161.9(d, J=246.2 Hz), 138.6, 138.4, 137.8, 135.8, 133.7, 131.5, 130.7, 130.1, 129.1, 127.9, 127.3, 125.4, 115.5 (d, J=21.8 Hz), 51.7, 20.6, 19.9, -2.2, -2.5 | |
| c4 | 7.50—7.43(m, 2H), 7.41—7.34(m, 3H), 7.30—7.25(m, 2H), 7.20—7.11(m, 4H), 7.09—7.04(m, 2H), 4.38(t, J=16.0 Hz, 1H), 2.24(s, 3H), 1.80—1.69(m, 1H), 1.47—1.37(m, 1H), 0.18(s, 6H) | 203.9, 138.7, 138.4, 138.3, 137.9, 133.7, 132.9, 131.6, 130.9, 129.9, 129.2, 128.8, 128.0, 127.4, 125.4, 51.9, 20.6, 19.9, -2.2, -2.4 | |
| c5 | 7.93—7.86(m, 2H), 7.49—7.46(m, 2H), 7.41—7.36(m, 3H), 7.30—7.27(m, 2H), 7.24—7.20(m, 2H), 7.15—7.10(m, 2H), 4.47(t, J=7.5 Hz, 1H), 3.91(s, 3H), 2.22(s, 3H), 1.85—1.79(m, 1H), 1.49—1.42(m, 1H), 0.21(s, 3H), 0.15(s, 3H) | 203.5, 166.9, 145.6, 138.2, 137.9, 133.7, 131.6, 130.9, 130.3, 130.0, 129.2, 128.9, 128.6, 128.0, 127.5, 125.4, 52.6, 52.1, 20.6, 19.9, -2.2, -2.5 | |
| c6 | 7.42—7.37(m, 2H), 7.33—7.26(m, 3H), 7.25—7.22(m, 1H), 7.19—7.16(m, 1H), 7.14—7.10(m, 2H), 7.09—7.01(m, 4H), 4.96(s, 2H), 4.37(t, J=7.4 Hz, 1H), 2.16(s, 3H), 2.02(s, 3H), 1.78—1.68(m, 1H), 1.39—1.31(m, 1H), 0.13(s, 3H), 0.09(s, 3H) | 203.9, 170.9, 140.5, 138.5, 138.4, 138.0, 134.6, 133.7, 131.6, 130.8, 129.1, 128.6, 128.5, 127.9, 127.6, 125.3, 65.9, 52.1, 21.0, 20.7, 20.1, -2.3, -2.4 | |
| c7 | 7.47—7.41(m, 4H), 7.36—7.33(m, 2H), 7.32—7.28(m, 2H), 7.27—7.22(m, 3H), 7.16—7.11(m, 2H), 4.48(t, J=7.5 Hz, 1H), 2.24(s, 3H), 1.84—1.75(m, 1H), 1.47—1.39(m, 1H), 0.22(s, 3H), 0.15(s, 3H) | 203.4, 144.4, 138.2, 138.1, 138.0, 133.7, 131.8, 131.1, 129.2, 128.9, 128.0, 127.6, 125.6, 125.6, 125.5, 121.4 (q, J=271.5 Hz), 52.2, 20.8, 20.2, -2.4, -2.4 | |
| Compd. | 1H NMR(400 M Hz, CDCl3), δ | 13C NMR(101 M Hz, CDCl3), δ | |
| c8 | 7.51—7.47(m, 2H), 7.39—7.34(m, 5H), 7.29—7.26(m, 1H), 7.22—7.15(m, 3H), 7.15—7.12(m, 2H), 4.45(t, J=8.0 Hz, 1H), 2.26(s, 3H), 1.89—1.79(m, 1H), 1.47—1.40(m, 1H), 0.26(s, 9H), 0.21(s, 3H), 0.19(s, 3H) | 204.1, 140.9, 138.9, 138.7, 138.6, 138.2, 133.7, 133.7, 131.6, 130.7, 129.1, 127.9, 127.8, 127.7, 125.4, 52.4, 20.8, 20.2, -2.4, -2.4 | |
| c9 | 7.51—7.46(m, 2H), 7.40—7.34(m, 3H), 7.28—7.22(m, 2H), 7.14—7.08(m, 2H), 7.07—7.02(m, 2H), 6.77—6.71(m, 2H), 4.35(t, J=7.5 Hz, 1H), 3.75(s, 3H), 2.20(s, 3H), 1.79—1.71(m, 1H), 1.49—1.41(m, 1H), 0.18(s, 3H), 0.16(s, 3H) | 204.7, 158.6, 139.0, 138.8, 137.7, 133.7, 132.0, 131.4, 130.5, 129.6, 129.0, 127.9, 127.3, 125.3, 114.1, 55.2, 51.7, 20.5, 19.7, -2.1, -2.5 | |
| c10 | 7.55—7.51(m, 2H), 7.43—7.38(m, 4H), 7.32—7.28(m, 3H), 7.17—7.11(m, 4H), 4.46(t, J=7.3 Hz, 1H), 2.27(s, 3H), 1.87—1.81(m, 1H), 1.51—1.47(m, 1H), 1.32(s, 9H), 0.23(s, 3H), 0.21(s, 3H) | 204.5, 149.9, 138.8, 138.1, 137.2, 133.8, 131.5, 130.6, 129.0, 128.1, 127.9, 127.6, 125.8, 125.6, 125.3, 52.0, 34.4, 31.4, 20.7, 20.1, -2.3, -2.5 | |
| c11 | 7.51—7.43(m, 2H), 7.42—7.34(m, 3H), 7.32—7.26(m, 2H), 7.18—7.11(m, 5H), 7.07—7.00(m, 1H), 4.38(t, J=8.0 Hz, 1H), 2.28(s, 3H), 1.83—1.70(m, 1H), 1.47—1.37(m, 1H), 0.24(s, 3H), 0.18(s, 3H) | 203.5, 142.4, 138.2, 138.2, 138.1, 134.4, 133.7, 131.7, 131.0, 129.9, 129.2, 128.6, 128.0, 127.6, 127.2, 126.7, 125.5, 52.1, 20.7, 20.2, -2.3, -2.4 | |
| c12 | 7.53—7.47(m, 2H), 7.41—7.35(m, 3H), 7.34—7.30(m, 1H), 7.30—7.26(m, 1H), 7.15—7.10(m, 3H), 6.77—6.67(m, 3H), 4.41(t, J=8.0 Hz, 1H), 3.74(s, 3H), 2.26(s, 3H), 1.85—1.74(m, 1H), 1.51—1.41(m, 1H), 0.20(s, 6H) | 204.1, 159.8, 141.9, 138.7, 137.9, 133.7, 131.5, 130.7, 129.6, 129.1, 127.9, 127.7, 127.5, 125.3, 121.0, 113.9, 112.6, 55.2, 52.6, 20.7, 19.9, -2.2, -2.5 | |
| c13 | 7.48—7.43(m, 3H), 7.41—7.36(m, 4H), 7.33—7.26(m, 4H), 7.18—7.13(m, 2H), 4.48(t, J=8.0 Hz, 1H), 2.26(s, 3H), 1.84—1.75(m, 1H), 1.52—1.43(m, 1H), 0.24(s, 3H), 0.15(s, 3H) | 203.6, 141.3, 138.1, 138.0, 133.7, 132.0, 131.9, 131.7, 131.1, 129.3, 129.1, 128.0, 127.5, 125.6, 125.5, 125.3, 123.9, 121.4(q, J=265.4 Hz), 52.2, 20.7, 20.3, -2.3, -2.5 | |
| c14 | 7.82—7.76(m, 2H), 7.42—7.38(m, 2H), 7.34—7.28(m, 4H), 7.27—7.24(m, 2H), 7.22—7.20(m, 1H), 7.11—7.05(m, 2H), 4.44(t, J=8.9 Hz, 1H), 3.86(s, 3H), 2.19(s, 3H), 1.78—1.70(m, 1H), 1.44—1.36(m, 1H), 0.15(s, 3H), 0.10(s, 3H) | 203.8, 166.9, 140.8, 138.3, 138.2, 138.0, 133.7, 133.1, 131.6, 130.9, 130.5, 129.7, 129.1, 128.7, 128.3, 127.9, 127.5, 125.5, 52.2, 52.2, 20.7, 20.23, -2.3, -2.4 | |
| c15 | 7.48—7.38(m, 3H), 7.36—7.29(m, 3H), 7.26—7.19(m, 2H), 7.15—7.07(m, 3H), 7.03—6.97(m, 1H), 6.94—6.86(m, 1H), 4.84(t, J=8.0 Hz, 1H), 2.33(s, 3H), 1.79—1.64(m, 1H), 1.44—1.34(m, 1H), 0.18(s, 6H) | 203.3, 161.1, 158.7, 138.5, 138.2, 137.8, 133.6, 131.6, 130.9, 129.6, 129.0, 128.7, 128.6, 127.8, 125.5, 124.4, 115.6(d, J=22.7 Hz), 43.5, 20.9, 19.1, -2.5, -2.6 | |
| c16 | 7.49—7.42(m, 3H), 7.36—7.29(m, 3H), 7.24—7.19(m, 1H), 7.17—7.13(m, 1H), 7.12—7.05(m, 3H), 6.74—6.67(m, 1H), 6.74—6.67(m, 1H), 4.99(t, J=8.0 Hz, 1H), 3.68(s, 3H), 2.34(s, 3H), 1.77—1.65(m, 1H), 1.40—1.34(m, 1H), 0.15(s, 6H) | 204.7, 156.1, 139.2, 138.3, 138.1, 133.7, 131.4, 130.5, 129.3, 128.8, 128.1, 128.0, 127.7, 125.6, 125.1, 120.8, 110.6, 55.2, 43.9, 20.9, 18.7, -2.4, -2.5 | |
| c17 | 7.45—7.34(m, 5H), 7.33—7.26(m, 5H), 7.24—7.19(m, 2H), 7.14—7.06(m, 2H), 6.95—6.80(m, 3H), 6.54—6.47(m, 1H), 4.65(t, J=12.0 Hz, 1H), 2.20(s, 3H), 1.98—1.86(m, 1H), 1.30—1.24(m, 1H), 0.19(s, 6H) | 204.4, 141.7, 141.1, 138.6, 138.5, 137.7, 133.8, 131.2, 130.8, 130.4, 130.2, 129.4, 129.0, 128.2, 128.0, 127.9, 127.8, 127.5, 127.0, 126.7, 125.2, 47.6, 20.6, 20.5, -1.9, -2.4 | |
| c18 | 7.52—7.48(m, 2H), 7.44—7.41(m, 1H), 7.36—7.31(m, 3H), 7.29—7.25(m, 3H), 7.18—7.12(m, 3H), 7.11—7.07(m, 1H), 5.09(t, J=8.0 Hz, 1H), 2.35(s, 3H), 1.80—1.73(m, 1H), 1.36—1.30(m, 1H), 0.25(s, 3H), 0.23(s, 3H) | 203.3, 138.6, 138.5, 138.4, 137.7, 133.7, 133.4, 131.6, 131.0, 129.8, 129.3, 129.1, 128.2, 128.1, 127.8, 127.1, 125.5, 47.5, 21.0, 19.9, -2.3, -2.5 | |
| c19 | 7.54—7.49(m, 2H), 7.40—7.35(m, 3H), 7.24—7.20(m, 2H), 7.13—7.10(m, 2H), 7.09—7.06(m, 2H), 7.06—7.03(m, 1H), 7.02—6.98(m, 1H), 4.64—4.58(m, 1H), 2.19(s, 3H), 1.98(s, 3H), 1.90—1.84(m, 1H), 1.35—1.30(m, 1H), 0.26(s, 3H), 0.19(s, 3H) | 204.6, 139.4, 138.9, 138.7, 137.4, 135.4, 133.8, 131.4, 130.7, 130.4, 129.2, 128.0, 127.8, 127.0, 126.9, 126.4, 125.3, 47.9, 20.3, 19.7, 19.6, -2.2, -2.3 | |
| c20 | 7.60—7.55(m, 1H), 7.51—7.42(m, 4H), 7.37—7.31(m, 3H), 7.28—7.22(m, 3H), 7.15—7.08(m, 2H), 4.95(t, J=8.0 Hz, 1H), 2.35(s, 3H), 1.83—1.73(m, 1H), 1.29—1.24(m, 1H), 0.27(s, 6H) | 203.0, 139.9, 138.4, 138.3, 137.6, 133.8, 132.0, 131.7, 131.1, 128.0, 129.6, 129.2, 127.9, 127.5, 126.9, 126.4, 125.5, 121.3(q, J=271.3 Hz), 47.1, 21.7, 20.9, -2.1, -2.5 | |
| Compd. | 1H NMR(400 M Hz, CDCl3), δ | 13C NMR(101 M Hz, CDCl3), δ | |
| c21 | 8.40(d, J=3.2 Hz, 1H), 8.33(d, J=2.4 Hz, 1H), 7.53—7.50(m, 1H), 7.44—7.40(m, 2H), 7.37—7.32(m, 3H), 7.30—7.28(m, 1H), 7.27—7.23(m, 1H), 7.15—7.10(m, 3H), 4.42(t, J=8.0 Hz, 1H), 2.24(s, 3H), 1.79—1.70(m, 1H), 1.45—1.36(m, 1H), 0.20(s, 3H), 0.13(s, 3H) | 203.4, 150.0, 148.4, 138.1, 137.9, 137.7, 135.9, 135.6, 133.6, 131.7, 131.1, 129.2, 128.0, 127.5, 125.5, 123.5, 49.6, 20.7, 20.1, -2.4, -2.5 | |
| c22 | 7.53—7.48(m, 2H), 7.42—7.38(m, 7H), 7.36—7.35(m, 1H), 7.24—7.19(m, 2H), 6.90—6.88(m, 1H), 6.33—6.28(m, 1H), 2.28(s, 3H), 1.67—1.64(m, 1H), 1.54(s, 3H), 1.46—1.42(m, 1H), 0.15(s, 3H), 0.11(s, 3H) | 209.3, 142.7, 140.0, 139.6, 135.9, 133.6, 130.9, 129.0, 128.8, 128.7, 127.8, 127.2, 127.1, 126.2, 124.6, 54.6, 28.4, 23.5, 20.3, -1.1, -1.4 | |
| c24 | 7.90—7.83(m, 2H), 7.51—7.43(m, 3H), 7.40—7.32(m, 5H), 7.18—7.12(m, 2H), 7.10—7.04(m, 2H), 4.60(t, J=8.0 Hz, 1H), 2.28(s, 3H), 1.86—1.76(m, 1H), 1.48—1.40(m, 1H), 0.17(s, 6H) | 200.4, 138.7, 138.3, 136.7, 136.6, 133.7, 132.7, 129.6, 129.0, 128.7, 128.5, 128.1, 127.8, 48.8, 21.2, 21.1, -2.3, -2.5 | |
| c25 | 7.90—7.82(m, 2H), 7.50—7.44(m, 2H), 7.39—7.31(m, 3H), 7.15—7.09(m, 2H), 7.09—7.04(m, 2H), 7.04—6.97(m, 2H), 4.52(t, J=8.0 Hz, 1H), 2.28(s, 3H), 1.83—1.74(m, 1H), 1.46—1.38(m, 1H), 0.17(s, 3H), 0.15(s, 3H) | 198.9, 166.7, 164.2, 138.6, 138.2, 136.7, 133.8, 133.0, 131.3(d, J=9.2 Hz), 129.7, 129.0, 128.0(d, J=17.0 Hz), 115.6(d, J=21.8 Hz), 48.9, 21.2, 21.1, -2.3, -2.5 | |
| c26 | 7.81—7.75(m, 2H), 7.50—7.46(m, 2H), 7.38—7.33(m, 3H), 7.18—7.11(m, 4H), 7.07—7.02(m, 2H), 4.57(t, J=8.0 Hz, 1H), 2.35(s, 3H), 2.27(s, 3H), 1.82—1.74(m, 1H), 1.44—1.37(m, 1H), 0.15(s, 3H), 0.14(s, 3H) | 200.0, 143.4, 138.9, 138.6, 136.5, 134.1, 133.8, 129.5, 129.2, 129.0, 128.8, 128.1, 127.8, 48.6, 21.6, 21.2, 21.1, -2.3, -2.5 | |
| c27 | 7.91—7.82(m, 2H), 7.51—7.44(m, 2H), 7.39—7.32(m, 3H), 7.18—7.10(m, 2H), 7.09—7.02(m, 2H), 6.87—6.79(m, 2H), 4.56(t, J=8.0 Hz, 1H), 3.81(s, 3H), 2.28(s, 3H), 1.86—1.74(m, 1H), 1.47—1.37(m, 1H), 0.17(s, 3H), 0.16(s, 3H) | 198.9, 163.1, 138.9, 138.8, 136.4, 133.7, 131.0, 129.5, 129.5, 129.0, 128.0, 127.8, 113.6, 55.4, 48.4, 21.2, 21.1, -2.3, -2.5 | |
| c28 | 7.84—7.80(m, 2H), 7.49—7.45(m, 2H), 7.39—7.33(m, 5H), 7.16—7.12(m, 2H), 7.07—7.03(m, 2H), 4.59(t, J=8.0 Hz, 1H), 2.28(s, 3H), 1.81—1.73(m, 1H), 1.45—1.39(m, 1H), 1.30(s, 9H), 0.15(s, 3H), 0.14(s, 3H) | 200.0, 156.3, 138.9, 138.6, 136.5, 134.0, 133.7, 129.5, 129.0, 128.7, 128.1, 127.8, 125.5, 48.7, 35.1, 31.1, 21.3, 21.1, -2.2, -2.5 | |
| c29 | 7.87—7.83(m, 2H), 7.48—7.43(m, 2H), 7.35—7.30(m, 3H), 7.17—7.12(m, 2H), 7.11—7.03(m, 4H), 4.50(t, J=8.0 Hz, 1H), 2.28(s, 3H), 1.81—1.73(m, 1H), 1.43—1.36(m, 1H), 0.17(s, 3H), 0.14(s, 3H) | 198.9, 152.3, 138.5, 138.0, 136.9, 134.8, 133.8, 130.7, 129.7, 129.1, 128.1, 127.9, 120.2, 49.1, 21.3, 21.1, -2.2, -2.5 | |
| c30 | 8.01—7.96(m, 2H), 7.87—7.81(m, 2H), 7.48—7.43(m, 2H), 7.38—7.31(m, 3H), 7.12—7.05(m, 2H), 7.05—7.02(m, 2H), 4.54(t, J=8.0 Hz, 1H), 3.91(s, 3H), 2.27(s, 3H), 1.83—1.75(m, 1H), 1.45—1.37(m, 1H), 0.17(s, 3H), 0.15(s, 3H) | 200.0, 166.3, 140.0, 138.5, 137.7, 136.8, 133.7, 133.3, 129.7, 129.1, 128.5, 128.1, 127.9, 52.4, 49.4, 21.1, -2.3, -2.5 | |
| c31 | 7.91—7.83(m, 2H), 7.61—7.54(m, 2H), 7.48—7.41(m, 2H), 7.37—7.29(m, 3H), 7.10—7.01(m, 4H), 4.50(t, J=8.0 Hz, 1H), 2.27(s, 3H), 1.84—1.70(m, 1H), 1.44—1.34(m, 1H), 0.15(s, 6H) | 199.5, 139.4, 138.5, 137.7, 137.0, 133.8, 129.8, 129.1, 129.0, 128.1, 127.9, 129.6, 125.5(d, J=3.9 Hz), 123.7(q, J=272.5 Hz), 49.5, 21.1, 21.1, -2.2, -2.5 | |
| c32 | 7.65—7.61(m, 1H), 7.55—7.49(m, 3H), 7.41—7.37(m, 3H), 7.36—7.33(m, 1H), 7.21—7.18(m, 1H), 7.15—7.08(m, 4H), 4.53(t, J=8.0 Hz, 1H), 2.32(s, 3H), 1.84—1.78(m, 1H), 1.48—1.41(m, 1H), 0.20(s, 3H), 0.19(s, 3H) | 199.2, 164.0, 138.5, 137.9, 136.8, 133.8, 130.15, 130.0, 129.7, 129.1, 128.1, 127.9, 124.4, 119.8(d, J=21.4 Hz), 115.5(d, J=22.2 Hz), 49.2, 21.2, 21.1, -2.2, -2.5 | |
| c33 | 7.65—7.60(m, 2H), 7.49—7.45(m, 2H), 7.36—7.31(m, 3H), 7.28—7.25(m, 1H), 7.24—7.20(m, 1H), 7.14—7.10(m, 2H), 7.06—7.02(m, 2H), 4.57(t, J=8.0 Hz, 1H), 2.33(s, 3H), 2.27(s, 3H), 1.80—1.74(m, 1H), 1.43—1.37(m, 1H), 0.14(s, 6H) | 200.8, 138.8, 138.4, 138.2, 136.7, 136.5, 133.82, 133.5, 129.5, 129.2, 129.0, 128.3, 128.1, 127.8, 125.9, 48.8, 21.4, 21.3, 21.1, -2.2, -2.4 | |
| Compd. | 1H NMR(400 M Hz, CDCl3), δ | 13C NMR(101 M Hz, CDCl3), δ | |
| c35 | 7.95—7.89(m, 2H), 7.52—7.48(m, 2H), 7.43—7.38(m, 3H), 7.34—7.31(m, 2H), 7.27—7.24(m, 2H), 7.20—7.17(m, 2H), 5.00—4.94(m, 1H), 4.57—4.50(m, 1H), 2.29(s, 3H), 2.18—2.14(m, 1H), 2.03—1.98(m, 1H), 1.88—1.84(m, 1H), 1.83—1.77(m, 3H), 1.63—1.57(m, 2H), 1.50—1.46(m, 1H), 1.19—1.14(m, 2H), 1.00—0.96(m, 6H), 0.84(d, J= 6.4 Hz, 3H), 0.27(s, 3H), 0.21(s, 3H) | 203.4, 165.9, 145.4, 138.2, 133.7, 131.7, 131.0, 130.2, 130.0, 129.5, 129.2, 128.5, 128.3, 127.9, 127.6, 125.4, 74.9, 52.5, 47.3, 41.0, 34.4, 31.5, 26.5, 23.6, 22.1, 20.9, 20.1, 16.5, -2.3 | |
| c36 | 7.90—7.84(m, 2H), 7.48—7.43(m, 2H), 7.39—7.33(m, 3H), 7.30—7.26(m, 2H), 7.22—7.17(m, 2H), 7.15—7.10(m, 2H), 5.24(s, 1H), 4.52—4.37(m, 1H), 2.25—2.20(m, 3H), 1.83—1.79(m, 2H), 1.65(s, 2H), 1.47—1.43(m, 6H), 1.41—1.31(m, 14H), 0.23—0.18(m, 3H), 0.17—0.13(m, 3H) | 203.5, 166.1, 145.3, 138.2, 138.0, 133.7, 131.7, 130.9, 129.9, 129.7, 129.2, 128.5, 128.0, 127.6, 125.4, 73.0, 52.5, 29.1, 24.2, 24.0, 23.4, 23.2, 20.9, 20.7, 20.0, -2.2, -2.4 | |
| c40 | 7.52—7.46(m, 3H), 7.35—7.32(m, 3H), 7.31—7.29(m, 2H), 7.29—7.28(m, 1H), 7.27—7.25(m, 5H), 7.24—7.23(m, 2H), 7.22—7.20(m, 1H), 7.18—7.15(m, 2H), 5.46(t, J=7.1 Hz, 1H), 4.36(t, J=7.5 Hz, 1H), 3.02—2.91(m, 1H), 2.56—2.49(m, 1H), 2.35(s, 3H), 2.32(s, 1H), 2.24(d, J=14.1 Hz, 1H), 0.13(s, 3H), 0.12(s, 3H) | 203.9, 144.5, 139.3, 139.0, 138.8, 138.7, 138.0, 133.6, 131.6, 130.9, 129.0, 128.8, 128.7, 128.4, 128.2, 128.1, 127.7, 127.2, 126.7, 125.4, 123.4, 56.9, 33.2, 20.8, -2.4 | 
Table 2 1H NMR and 13C NMR data of target compounds c1—c40
| Compd. | 1H NMR(400 M Hz, CDCl3), δ | 13C NMR(101 M Hz, CDCl3), δ | |
|---|---|---|---|
| c1 | 7.40—7.34(m, 2H), 7.28—7.22(m, 3H), 7.18—7.12(m, 2H), 6.99(d, J=7.4 Hz, 2H), 6.91—6.85(m, 4H), 4.26(t, J=7.5 Hz, 1H), 2.16(s, 3H), 2.10(s, 3H), 1.66 (m, 1H), 1.32(m, 1H), 0.06(s, 3H), 0.04(s, 3H) | 204.5, 138.8, 138.8, 137.8, 137.2, 136.6, 133.8, 131.5, 130.6, 129.4, 129.0, 128.4, 127.9, 127.5, 125.3, 52.2, 21.1, 20.6, 19.8, -2.2, -2.5 | |
| c2 | 7.53—7.48(m, 2H), 7.42—7.36(m, 3H), 7.31(d, J=7.8 Hz, 1H), 7.28—7.25(m, 1H), 7.24—7.21(m, 2H), 7.19—7.14(m, 3H), 7.12(d, J=7.8 Hz, 2H), 4.43(t, J =7.6 Hz, 1H), 2.23(s, 3H), 1.85—1.77(m, 1H), 1.52—1.44(m, 1H), 0.18(d, J =11.4 Hz, 6H) | 204.4, 140.2, 138.8, 138.6, 137.8, 133.7, 131.5, 130.6, 129.1, 128.7, 128.6, 127.9, 127.4, 127.0, 125.3, 52.6, 20.6, 19.9, -2.2, -2.5 | |
| c3 | 7.50—7.43(m, 2H), 7.42—7.35(m, 3H), 7.30—7.24(m, 2H), 7.17—7.07(m, 4H), 6.95—6.86(m, 2H), 4.40(t, J=8.0 Hz, 1H), 2.24(s, 3H), 1.82—1.69(m, 1H), 1.51—1.40(m, 1H), 0.17(s, 6H) | 204.3, 161.9(d, J=246.2 Hz), 138.6, 138.4, 137.8, 135.8, 133.7, 131.5, 130.7, 130.1, 129.1, 127.9, 127.3, 125.4, 115.5 (d, J=21.8 Hz), 51.7, 20.6, 19.9, -2.2, -2.5 | |
| c4 | 7.50—7.43(m, 2H), 7.41—7.34(m, 3H), 7.30—7.25(m, 2H), 7.20—7.11(m, 4H), 7.09—7.04(m, 2H), 4.38(t, J=16.0 Hz, 1H), 2.24(s, 3H), 1.80—1.69(m, 1H), 1.47—1.37(m, 1H), 0.18(s, 6H) | 203.9, 138.7, 138.4, 138.3, 137.9, 133.7, 132.9, 131.6, 130.9, 129.9, 129.2, 128.8, 128.0, 127.4, 125.4, 51.9, 20.6, 19.9, -2.2, -2.4 | |
| c5 | 7.93—7.86(m, 2H), 7.49—7.46(m, 2H), 7.41—7.36(m, 3H), 7.30—7.27(m, 2H), 7.24—7.20(m, 2H), 7.15—7.10(m, 2H), 4.47(t, J=7.5 Hz, 1H), 3.91(s, 3H), 2.22(s, 3H), 1.85—1.79(m, 1H), 1.49—1.42(m, 1H), 0.21(s, 3H), 0.15(s, 3H) | 203.5, 166.9, 145.6, 138.2, 137.9, 133.7, 131.6, 130.9, 130.3, 130.0, 129.2, 128.9, 128.6, 128.0, 127.5, 125.4, 52.6, 52.1, 20.6, 19.9, -2.2, -2.5 | |
| c6 | 7.42—7.37(m, 2H), 7.33—7.26(m, 3H), 7.25—7.22(m, 1H), 7.19—7.16(m, 1H), 7.14—7.10(m, 2H), 7.09—7.01(m, 4H), 4.96(s, 2H), 4.37(t, J=7.4 Hz, 1H), 2.16(s, 3H), 2.02(s, 3H), 1.78—1.68(m, 1H), 1.39—1.31(m, 1H), 0.13(s, 3H), 0.09(s, 3H) | 203.9, 170.9, 140.5, 138.5, 138.4, 138.0, 134.6, 133.7, 131.6, 130.8, 129.1, 128.6, 128.5, 127.9, 127.6, 125.3, 65.9, 52.1, 21.0, 20.7, 20.1, -2.3, -2.4 | |
| c7 | 7.47—7.41(m, 4H), 7.36—7.33(m, 2H), 7.32—7.28(m, 2H), 7.27—7.22(m, 3H), 7.16—7.11(m, 2H), 4.48(t, J=7.5 Hz, 1H), 2.24(s, 3H), 1.84—1.75(m, 1H), 1.47—1.39(m, 1H), 0.22(s, 3H), 0.15(s, 3H) | 203.4, 144.4, 138.2, 138.1, 138.0, 133.7, 131.8, 131.1, 129.2, 128.9, 128.0, 127.6, 125.6, 125.6, 125.5, 121.4 (q, J=271.5 Hz), 52.2, 20.8, 20.2, -2.4, -2.4 | |
| Compd. | 1H NMR(400 M Hz, CDCl3), δ | 13C NMR(101 M Hz, CDCl3), δ | |
| c8 | 7.51—7.47(m, 2H), 7.39—7.34(m, 5H), 7.29—7.26(m, 1H), 7.22—7.15(m, 3H), 7.15—7.12(m, 2H), 4.45(t, J=8.0 Hz, 1H), 2.26(s, 3H), 1.89—1.79(m, 1H), 1.47—1.40(m, 1H), 0.26(s, 9H), 0.21(s, 3H), 0.19(s, 3H) | 204.1, 140.9, 138.9, 138.7, 138.6, 138.2, 133.7, 133.7, 131.6, 130.7, 129.1, 127.9, 127.8, 127.7, 125.4, 52.4, 20.8, 20.2, -2.4, -2.4 | |
| c9 | 7.51—7.46(m, 2H), 7.40—7.34(m, 3H), 7.28—7.22(m, 2H), 7.14—7.08(m, 2H), 7.07—7.02(m, 2H), 6.77—6.71(m, 2H), 4.35(t, J=7.5 Hz, 1H), 3.75(s, 3H), 2.20(s, 3H), 1.79—1.71(m, 1H), 1.49—1.41(m, 1H), 0.18(s, 3H), 0.16(s, 3H) | 204.7, 158.6, 139.0, 138.8, 137.7, 133.7, 132.0, 131.4, 130.5, 129.6, 129.0, 127.9, 127.3, 125.3, 114.1, 55.2, 51.7, 20.5, 19.7, -2.1, -2.5 | |
| c10 | 7.55—7.51(m, 2H), 7.43—7.38(m, 4H), 7.32—7.28(m, 3H), 7.17—7.11(m, 4H), 4.46(t, J=7.3 Hz, 1H), 2.27(s, 3H), 1.87—1.81(m, 1H), 1.51—1.47(m, 1H), 1.32(s, 9H), 0.23(s, 3H), 0.21(s, 3H) | 204.5, 149.9, 138.8, 138.1, 137.2, 133.8, 131.5, 130.6, 129.0, 128.1, 127.9, 127.6, 125.8, 125.6, 125.3, 52.0, 34.4, 31.4, 20.7, 20.1, -2.3, -2.5 | |
| c11 | 7.51—7.43(m, 2H), 7.42—7.34(m, 3H), 7.32—7.26(m, 2H), 7.18—7.11(m, 5H), 7.07—7.00(m, 1H), 4.38(t, J=8.0 Hz, 1H), 2.28(s, 3H), 1.83—1.70(m, 1H), 1.47—1.37(m, 1H), 0.24(s, 3H), 0.18(s, 3H) | 203.5, 142.4, 138.2, 138.2, 138.1, 134.4, 133.7, 131.7, 131.0, 129.9, 129.2, 128.6, 128.0, 127.6, 127.2, 126.7, 125.5, 52.1, 20.7, 20.2, -2.3, -2.4 | |
| c12 | 7.53—7.47(m, 2H), 7.41—7.35(m, 3H), 7.34—7.30(m, 1H), 7.30—7.26(m, 1H), 7.15—7.10(m, 3H), 6.77—6.67(m, 3H), 4.41(t, J=8.0 Hz, 1H), 3.74(s, 3H), 2.26(s, 3H), 1.85—1.74(m, 1H), 1.51—1.41(m, 1H), 0.20(s, 6H) | 204.1, 159.8, 141.9, 138.7, 137.9, 133.7, 131.5, 130.7, 129.6, 129.1, 127.9, 127.7, 127.5, 125.3, 121.0, 113.9, 112.6, 55.2, 52.6, 20.7, 19.9, -2.2, -2.5 | |
| c13 | 7.48—7.43(m, 3H), 7.41—7.36(m, 4H), 7.33—7.26(m, 4H), 7.18—7.13(m, 2H), 4.48(t, J=8.0 Hz, 1H), 2.26(s, 3H), 1.84—1.75(m, 1H), 1.52—1.43(m, 1H), 0.24(s, 3H), 0.15(s, 3H) | 203.6, 141.3, 138.1, 138.0, 133.7, 132.0, 131.9, 131.7, 131.1, 129.3, 129.1, 128.0, 127.5, 125.6, 125.5, 125.3, 123.9, 121.4(q, J=265.4 Hz), 52.2, 20.7, 20.3, -2.3, -2.5 | |
| c14 | 7.82—7.76(m, 2H), 7.42—7.38(m, 2H), 7.34—7.28(m, 4H), 7.27—7.24(m, 2H), 7.22—7.20(m, 1H), 7.11—7.05(m, 2H), 4.44(t, J=8.9 Hz, 1H), 3.86(s, 3H), 2.19(s, 3H), 1.78—1.70(m, 1H), 1.44—1.36(m, 1H), 0.15(s, 3H), 0.10(s, 3H) | 203.8, 166.9, 140.8, 138.3, 138.2, 138.0, 133.7, 133.1, 131.6, 130.9, 130.5, 129.7, 129.1, 128.7, 128.3, 127.9, 127.5, 125.5, 52.2, 52.2, 20.7, 20.23, -2.3, -2.4 | |
| c15 | 7.48—7.38(m, 3H), 7.36—7.29(m, 3H), 7.26—7.19(m, 2H), 7.15—7.07(m, 3H), 7.03—6.97(m, 1H), 6.94—6.86(m, 1H), 4.84(t, J=8.0 Hz, 1H), 2.33(s, 3H), 1.79—1.64(m, 1H), 1.44—1.34(m, 1H), 0.18(s, 6H) | 203.3, 161.1, 158.7, 138.5, 138.2, 137.8, 133.6, 131.6, 130.9, 129.6, 129.0, 128.7, 128.6, 127.8, 125.5, 124.4, 115.6(d, J=22.7 Hz), 43.5, 20.9, 19.1, -2.5, -2.6 | |
| c16 | 7.49—7.42(m, 3H), 7.36—7.29(m, 3H), 7.24—7.19(m, 1H), 7.17—7.13(m, 1H), 7.12—7.05(m, 3H), 6.74—6.67(m, 1H), 6.74—6.67(m, 1H), 4.99(t, J=8.0 Hz, 1H), 3.68(s, 3H), 2.34(s, 3H), 1.77—1.65(m, 1H), 1.40—1.34(m, 1H), 0.15(s, 6H) | 204.7, 156.1, 139.2, 138.3, 138.1, 133.7, 131.4, 130.5, 129.3, 128.8, 128.1, 128.0, 127.7, 125.6, 125.1, 120.8, 110.6, 55.2, 43.9, 20.9, 18.7, -2.4, -2.5 | |
| c17 | 7.45—7.34(m, 5H), 7.33—7.26(m, 5H), 7.24—7.19(m, 2H), 7.14—7.06(m, 2H), 6.95—6.80(m, 3H), 6.54—6.47(m, 1H), 4.65(t, J=12.0 Hz, 1H), 2.20(s, 3H), 1.98—1.86(m, 1H), 1.30—1.24(m, 1H), 0.19(s, 6H) | 204.4, 141.7, 141.1, 138.6, 138.5, 137.7, 133.8, 131.2, 130.8, 130.4, 130.2, 129.4, 129.0, 128.2, 128.0, 127.9, 127.8, 127.5, 127.0, 126.7, 125.2, 47.6, 20.6, 20.5, -1.9, -2.4 | |
| c18 | 7.52—7.48(m, 2H), 7.44—7.41(m, 1H), 7.36—7.31(m, 3H), 7.29—7.25(m, 3H), 7.18—7.12(m, 3H), 7.11—7.07(m, 1H), 5.09(t, J=8.0 Hz, 1H), 2.35(s, 3H), 1.80—1.73(m, 1H), 1.36—1.30(m, 1H), 0.25(s, 3H), 0.23(s, 3H) | 203.3, 138.6, 138.5, 138.4, 137.7, 133.7, 133.4, 131.6, 131.0, 129.8, 129.3, 129.1, 128.2, 128.1, 127.8, 127.1, 125.5, 47.5, 21.0, 19.9, -2.3, -2.5 | |
| c19 | 7.54—7.49(m, 2H), 7.40—7.35(m, 3H), 7.24—7.20(m, 2H), 7.13—7.10(m, 2H), 7.09—7.06(m, 2H), 7.06—7.03(m, 1H), 7.02—6.98(m, 1H), 4.64—4.58(m, 1H), 2.19(s, 3H), 1.98(s, 3H), 1.90—1.84(m, 1H), 1.35—1.30(m, 1H), 0.26(s, 3H), 0.19(s, 3H) | 204.6, 139.4, 138.9, 138.7, 137.4, 135.4, 133.8, 131.4, 130.7, 130.4, 129.2, 128.0, 127.8, 127.0, 126.9, 126.4, 125.3, 47.9, 20.3, 19.7, 19.6, -2.2, -2.3 | |
| c20 | 7.60—7.55(m, 1H), 7.51—7.42(m, 4H), 7.37—7.31(m, 3H), 7.28—7.22(m, 3H), 7.15—7.08(m, 2H), 4.95(t, J=8.0 Hz, 1H), 2.35(s, 3H), 1.83—1.73(m, 1H), 1.29—1.24(m, 1H), 0.27(s, 6H) | 203.0, 139.9, 138.4, 138.3, 137.6, 133.8, 132.0, 131.7, 131.1, 128.0, 129.6, 129.2, 127.9, 127.5, 126.9, 126.4, 125.5, 121.3(q, J=271.3 Hz), 47.1, 21.7, 20.9, -2.1, -2.5 | |
| Compd. | 1H NMR(400 M Hz, CDCl3), δ | 13C NMR(101 M Hz, CDCl3), δ | |
| c21 | 8.40(d, J=3.2 Hz, 1H), 8.33(d, J=2.4 Hz, 1H), 7.53—7.50(m, 1H), 7.44—7.40(m, 2H), 7.37—7.32(m, 3H), 7.30—7.28(m, 1H), 7.27—7.23(m, 1H), 7.15—7.10(m, 3H), 4.42(t, J=8.0 Hz, 1H), 2.24(s, 3H), 1.79—1.70(m, 1H), 1.45—1.36(m, 1H), 0.20(s, 3H), 0.13(s, 3H) | 203.4, 150.0, 148.4, 138.1, 137.9, 137.7, 135.9, 135.6, 133.6, 131.7, 131.1, 129.2, 128.0, 127.5, 125.5, 123.5, 49.6, 20.7, 20.1, -2.4, -2.5 | |
| c22 | 7.53—7.48(m, 2H), 7.42—7.38(m, 7H), 7.36—7.35(m, 1H), 7.24—7.19(m, 2H), 6.90—6.88(m, 1H), 6.33—6.28(m, 1H), 2.28(s, 3H), 1.67—1.64(m, 1H), 1.54(s, 3H), 1.46—1.42(m, 1H), 0.15(s, 3H), 0.11(s, 3H) | 209.3, 142.7, 140.0, 139.6, 135.9, 133.6, 130.9, 129.0, 128.8, 128.7, 127.8, 127.2, 127.1, 126.2, 124.6, 54.6, 28.4, 23.5, 20.3, -1.1, -1.4 | |
| c24 | 7.90—7.83(m, 2H), 7.51—7.43(m, 3H), 7.40—7.32(m, 5H), 7.18—7.12(m, 2H), 7.10—7.04(m, 2H), 4.60(t, J=8.0 Hz, 1H), 2.28(s, 3H), 1.86—1.76(m, 1H), 1.48—1.40(m, 1H), 0.17(s, 6H) | 200.4, 138.7, 138.3, 136.7, 136.6, 133.7, 132.7, 129.6, 129.0, 128.7, 128.5, 128.1, 127.8, 48.8, 21.2, 21.1, -2.3, -2.5 | |
| c25 | 7.90—7.82(m, 2H), 7.50—7.44(m, 2H), 7.39—7.31(m, 3H), 7.15—7.09(m, 2H), 7.09—7.04(m, 2H), 7.04—6.97(m, 2H), 4.52(t, J=8.0 Hz, 1H), 2.28(s, 3H), 1.83—1.74(m, 1H), 1.46—1.38(m, 1H), 0.17(s, 3H), 0.15(s, 3H) | 198.9, 166.7, 164.2, 138.6, 138.2, 136.7, 133.8, 133.0, 131.3(d, J=9.2 Hz), 129.7, 129.0, 128.0(d, J=17.0 Hz), 115.6(d, J=21.8 Hz), 48.9, 21.2, 21.1, -2.3, -2.5 | |
| c26 | 7.81—7.75(m, 2H), 7.50—7.46(m, 2H), 7.38—7.33(m, 3H), 7.18—7.11(m, 4H), 7.07—7.02(m, 2H), 4.57(t, J=8.0 Hz, 1H), 2.35(s, 3H), 2.27(s, 3H), 1.82—1.74(m, 1H), 1.44—1.37(m, 1H), 0.15(s, 3H), 0.14(s, 3H) | 200.0, 143.4, 138.9, 138.6, 136.5, 134.1, 133.8, 129.5, 129.2, 129.0, 128.8, 128.1, 127.8, 48.6, 21.6, 21.2, 21.1, -2.3, -2.5 | |
| c27 | 7.91—7.82(m, 2H), 7.51—7.44(m, 2H), 7.39—7.32(m, 3H), 7.18—7.10(m, 2H), 7.09—7.02(m, 2H), 6.87—6.79(m, 2H), 4.56(t, J=8.0 Hz, 1H), 3.81(s, 3H), 2.28(s, 3H), 1.86—1.74(m, 1H), 1.47—1.37(m, 1H), 0.17(s, 3H), 0.16(s, 3H) | 198.9, 163.1, 138.9, 138.8, 136.4, 133.7, 131.0, 129.5, 129.5, 129.0, 128.0, 127.8, 113.6, 55.4, 48.4, 21.2, 21.1, -2.3, -2.5 | |
| c28 | 7.84—7.80(m, 2H), 7.49—7.45(m, 2H), 7.39—7.33(m, 5H), 7.16—7.12(m, 2H), 7.07—7.03(m, 2H), 4.59(t, J=8.0 Hz, 1H), 2.28(s, 3H), 1.81—1.73(m, 1H), 1.45—1.39(m, 1H), 1.30(s, 9H), 0.15(s, 3H), 0.14(s, 3H) | 200.0, 156.3, 138.9, 138.6, 136.5, 134.0, 133.7, 129.5, 129.0, 128.7, 128.1, 127.8, 125.5, 48.7, 35.1, 31.1, 21.3, 21.1, -2.2, -2.5 | |
| c29 | 7.87—7.83(m, 2H), 7.48—7.43(m, 2H), 7.35—7.30(m, 3H), 7.17—7.12(m, 2H), 7.11—7.03(m, 4H), 4.50(t, J=8.0 Hz, 1H), 2.28(s, 3H), 1.81—1.73(m, 1H), 1.43—1.36(m, 1H), 0.17(s, 3H), 0.14(s, 3H) | 198.9, 152.3, 138.5, 138.0, 136.9, 134.8, 133.8, 130.7, 129.7, 129.1, 128.1, 127.9, 120.2, 49.1, 21.3, 21.1, -2.2, -2.5 | |
| c30 | 8.01—7.96(m, 2H), 7.87—7.81(m, 2H), 7.48—7.43(m, 2H), 7.38—7.31(m, 3H), 7.12—7.05(m, 2H), 7.05—7.02(m, 2H), 4.54(t, J=8.0 Hz, 1H), 3.91(s, 3H), 2.27(s, 3H), 1.83—1.75(m, 1H), 1.45—1.37(m, 1H), 0.17(s, 3H), 0.15(s, 3H) | 200.0, 166.3, 140.0, 138.5, 137.7, 136.8, 133.7, 133.3, 129.7, 129.1, 128.5, 128.1, 127.9, 52.4, 49.4, 21.1, -2.3, -2.5 | |
| c31 | 7.91—7.83(m, 2H), 7.61—7.54(m, 2H), 7.48—7.41(m, 2H), 7.37—7.29(m, 3H), 7.10—7.01(m, 4H), 4.50(t, J=8.0 Hz, 1H), 2.27(s, 3H), 1.84—1.70(m, 1H), 1.44—1.34(m, 1H), 0.15(s, 6H) | 199.5, 139.4, 138.5, 137.7, 137.0, 133.8, 129.8, 129.1, 129.0, 128.1, 127.9, 129.6, 125.5(d, J=3.9 Hz), 123.7(q, J=272.5 Hz), 49.5, 21.1, 21.1, -2.2, -2.5 | |
| c32 | 7.65—7.61(m, 1H), 7.55—7.49(m, 3H), 7.41—7.37(m, 3H), 7.36—7.33(m, 1H), 7.21—7.18(m, 1H), 7.15—7.08(m, 4H), 4.53(t, J=8.0 Hz, 1H), 2.32(s, 3H), 1.84—1.78(m, 1H), 1.48—1.41(m, 1H), 0.20(s, 3H), 0.19(s, 3H) | 199.2, 164.0, 138.5, 137.9, 136.8, 133.8, 130.15, 130.0, 129.7, 129.1, 128.1, 127.9, 124.4, 119.8(d, J=21.4 Hz), 115.5(d, J=22.2 Hz), 49.2, 21.2, 21.1, -2.2, -2.5 | |
| c33 | 7.65—7.60(m, 2H), 7.49—7.45(m, 2H), 7.36—7.31(m, 3H), 7.28—7.25(m, 1H), 7.24—7.20(m, 1H), 7.14—7.10(m, 2H), 7.06—7.02(m, 2H), 4.57(t, J=8.0 Hz, 1H), 2.33(s, 3H), 2.27(s, 3H), 1.80—1.74(m, 1H), 1.43—1.37(m, 1H), 0.14(s, 6H) | 200.8, 138.8, 138.4, 138.2, 136.7, 136.5, 133.82, 133.5, 129.5, 129.2, 129.0, 128.3, 128.1, 127.8, 125.9, 48.8, 21.4, 21.3, 21.1, -2.2, -2.4 | |
| Compd. | 1H NMR(400 M Hz, CDCl3), δ | 13C NMR(101 M Hz, CDCl3), δ | |
| c35 | 7.95—7.89(m, 2H), 7.52—7.48(m, 2H), 7.43—7.38(m, 3H), 7.34—7.31(m, 2H), 7.27—7.24(m, 2H), 7.20—7.17(m, 2H), 5.00—4.94(m, 1H), 4.57—4.50(m, 1H), 2.29(s, 3H), 2.18—2.14(m, 1H), 2.03—1.98(m, 1H), 1.88—1.84(m, 1H), 1.83—1.77(m, 3H), 1.63—1.57(m, 2H), 1.50—1.46(m, 1H), 1.19—1.14(m, 2H), 1.00—0.96(m, 6H), 0.84(d, J= 6.4 Hz, 3H), 0.27(s, 3H), 0.21(s, 3H) | 203.4, 165.9, 145.4, 138.2, 133.7, 131.7, 131.0, 130.2, 130.0, 129.5, 129.2, 128.5, 128.3, 127.9, 127.6, 125.4, 74.9, 52.5, 47.3, 41.0, 34.4, 31.5, 26.5, 23.6, 22.1, 20.9, 20.1, 16.5, -2.3 | |
| c36 | 7.90—7.84(m, 2H), 7.48—7.43(m, 2H), 7.39—7.33(m, 3H), 7.30—7.26(m, 2H), 7.22—7.17(m, 2H), 7.15—7.10(m, 2H), 5.24(s, 1H), 4.52—4.37(m, 1H), 2.25—2.20(m, 3H), 1.83—1.79(m, 2H), 1.65(s, 2H), 1.47—1.43(m, 6H), 1.41—1.31(m, 14H), 0.23—0.18(m, 3H), 0.17—0.13(m, 3H) | 203.5, 166.1, 145.3, 138.2, 138.0, 133.7, 131.7, 130.9, 129.9, 129.7, 129.2, 128.5, 128.0, 127.6, 125.4, 73.0, 52.5, 29.1, 24.2, 24.0, 23.4, 23.2, 20.9, 20.7, 20.0, -2.2, -2.4 | |
| c40 | 7.52—7.46(m, 3H), 7.35—7.32(m, 3H), 7.31—7.29(m, 2H), 7.29—7.28(m, 1H), 7.27—7.25(m, 5H), 7.24—7.23(m, 2H), 7.22—7.20(m, 1H), 7.18—7.15(m, 2H), 5.46(t, J=7.1 Hz, 1H), 4.36(t, J=7.5 Hz, 1H), 3.02—2.91(m, 1H), 2.56—2.49(m, 1H), 2.35(s, 3H), 2.32(s, 1H), 2.24(d, J=14.1 Hz, 1H), 0.13(s, 3H), 0.12(s, 3H) | 203.9, 144.5, 139.3, 139.0, 138.8, 138.7, 138.0, 133.6, 131.6, 130.9, 129.0, 128.8, 128.7, 128.4, 128.2, 128.1, 127.7, 127.2, 126.7, 125.4, 123.4, 56.9, 33.2, 20.8, -2.4 | 
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