环己酮与丙烯酸甲酯及(S)-3-(2′-氧环己基)-丙酸与醇的酯化反应

高等学校化学学报 ›› 2006, Vol. 27 ›› Issue (5): 894.doi:

环己酮与丙烯酸甲酯及(S)-3-(2′-氧环己基)-丙酸与醇的酯化反应

王会萍^1,3, 商艳梅¹, 王磊¹, 李叶芝^1,2, 黄化民¹

1.吉林大学化学学院, 2. 吉林大学超分子结构与材料教育部重点实验室,
3.吉林大学理论化学研究所, 理论化学计算国家重点实验室, 长春 130023

收稿日期:1900-01-01 修回日期:1900-01-01 出版日期:2006-05-10 发布日期:2006-05-10
通讯作者: 李叶芝

Esterifications of Cyclohexanone with Methyl Acrylate and (S)-3-(2′-Oxocyclohexyl)-propionic Acid with Alcohols

WANG Hui-Ping^1,3, SHANG Yan-Mei¹, WANG Lei¹, LI Ye-Zhi^1,2*, HUANG Hua-Min¹

1. College of Chemistry, 2. Key Laboratory of Supramolecular Structure and Material, Ministry of Education, 3. State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun 130023, China

Received:1900-01-01 Revised:1900-01-01 Online:2006-05-10 Published:2006-05-10
Contact: Li Ye-Zhi

摘要/Abstract

摘要：

在(R)TTCA·K催化下由环己酮直接与丙烯酸甲酯进行Michael加成反应得到了(S)-3-(2′-氧环己基)-丙酸甲酯, [α]²⁰_D-4.14(41.5% e.e.).

关键词: Fe₂(SO₄)₃·xH₂O; 光活性3-(2′-氧环己基)-丙酸甲酯; 光活性3-(2′-氧环己基)-丙酸乙酯; 光活性3-(2′-氧环己基)-丙酸丁酯; (R)-四氢噻唑-2-硫酮-4-羧酸钾盐

Abstract:

The esterification of carboxylic acid with alcohol in the presence of catalytic amounts of mineral acids is one of the most methods for preparing esters. The catalysts generally preferred are sulfuric acid or p\|toluenesulfonic acid. But the products esters were racemic when (S)-3-(2′-oxocyclohexyl) propionic acid reacts with alcohols in the presence of sulfuric acid or with p\|toluenesulfonic acid as catalyst. We replace sulfuric acid with Fe₂(SO₄)^₃·xH2O as the catalyst. The optical compound (S)-methy-3-(2′-oxocyclohexyl)propionate, (S)-ethyl-3-(2′-oxocyclohexyl)propionate and (S)-n-butyl-3-(2′-oxocyclohexyl)propionate were obtained. In this paper we also reported that cyclohexanone reacted with methyl acrylate in the presence of potassium thiazolidine-2-thione-4-carboxylate (R)TTCA·K as the chiral catalyst to afford optically active (S)-3-(2′-oxocy-clohexyl) propionate. The mechanism of reaction of cyclohexanone with methyl acrylate in the presence of (R)TTCA·K as the catalyst would be a complex process.

Key words: Fe₂(SO₄)₃·xH₂O; Optically active methyl-3-(2′-oxocyclohexyl)-propionate; Optically active ethyl-3-(2′-oxocyclohexyl)propionate; Optically active n\, butyl-3-(2′-oxocy-clohexyl)propionate; (R)-potassium thiazolidine-2-thione-4-carboxylate

中图分类号:

O621
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王会萍,商艳梅, 王磊, 李叶芝, 黄化民 . 环己酮与丙烯酸甲酯及(S)-3-(2′-氧环己基)-丙酸与醇的酯化反应. 高等学校化学学报, 2006, 27(5): 894.

WANG Hui-Ping^1,3, SHANG Yan-Mei¹, WANG Lei¹, LI Ye-Zhi^1,2*, HUANG Hua-Min¹. Esterifications of Cyclohexanone with Methyl Acrylate and (S)-3-(2′-Oxocyclohexyl)-propionic Acid with Alcohols. Chem. J. Chinese Universities, 2006, 27(5): 894.