diethyl 2-(phenylthio)succinate | 32822-17-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: diethyl 2-(phenylthio)succinate
• 英文别名: Phenylmercapto-bernsteinsaeure-diaethylester；Diethyl 2-phenylsulfanylbutanedioate
• CAS: 32822-17-6
• 化学式: C₁₄H₁₈O₄S
• 分子量: 282.361
• InChiKey: LXOVYUBSUITIIK-UHFFFAOYSA-N

物化性质

• 沸点：
  386.0±32.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(phenylthio)succinate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 0.33h， 生成 [(3E)-4-methoxybuta-1,3-dien-2-yl]sulfinylbenzene
  参考文献：
  名称：

  Adams, Harry; Anderson, James C.; Bell, Richard, Journal of the Chemical Society. Perkin transactions I, 1998, # 23, p. 3967 - 3973

  摘要：

  DOI：
• 作为产物：
  描述：

  苯硫酚 、 but-2-enedioic acid diethyl ester 在 lithium hydroxide 作用下， 生成 diethyl 2-(phenylthio)succinate
  参考文献：
  名称：

  热分解诱导的涉及异氰化物和生成亚硫酸的亚砜的两组分或多组分串联反应：获得多种含硫功能支架

  摘要：

  异氰酸酯与一些产生亚磺酸的亚砜的直接反应导致以高至高收率有效地形成相应的硫代氨基甲酸S-酯。还开发了涉及异氰酸酯，亚砜和合适的亲核试剂的多组分反应，可轻松获得各种范围的含硫化合物，包括异硫脲，碳亚氨基硫代酸酯和羧亚氨基硫代酸酯。

  DOI：

  10.1021/acs.orglett.7b03593

文献信息

• A Simple, Efficient, and Green Procedure for the 1,4-Addition of Thiols to Conjugated Alkenes and Alkynes Catalyzed by Sodium Acetate in Aqueous Medium
  作者：Brindaban C. Ranu、Tanmay Mandal

  DOI：10.1071/ch06455

  日期：——

  A benign and inexpensive salt, sodium acetate, efficiently catalyzes 1,4-addition of thiols to a variety of conjugated alkenes such as α,β-unsaturated ketones, aldehydes, carboxylic esters, nitriles, nitro compounds, and chalcones in aqueous THF. The reactions are clean, fast, and high yielding.

  一种温和且廉价的盐乙酸钠可在 THF 水溶液中有效催化硫醇与各种共轭烯烃（例如 α,β-不饱和酮、醛、羧酸酯、腈、硝基化合物和查耳酮）的 1,4-加成反应。反应干净、快速且产率高。
• Catalysis by an ionic liquid: efficient conjugate addition of thiols to electron deficient alkenes catalyzed by molten tetrabutylammonium bromide under solvent-free conditions
  作者：Brindaban C Ranu、Suvendu S Dey、Alakananda Hajra

  DOI：10.1016/s0040-4020(03)00289-8

  日期：2003.3

  An inexpensive and readily available ionic liquid, tetrabutylammonium bromide in the molten state, efficiently catalyzes the conjugate addition of thiols to α,β-unsaturated nitriles, carboxylic ester, ketones and aldehydes as well as nitro olefins.

  一种廉价且易于获得的离子液体，熔融态的四丁基溴化铵，可有效催化硫醇与α，β-不饱和腈，羧酸酯，酮和醛以及硝基烯烃的共轭加成反应。
• Efficient Synthesis of β‐Alkyl/Arylsulfanyl Carbonyl Compounds by In‐TMSCl‐Promoted Cleavage of Dialkyl/Diaryl Disulfides and Subsequent Michael Addition
  作者：Brindaban C. Ranu、Tanmay Mandal

  DOI：10.1080/00397910701229859

  日期：2007.5

  Abstract A convenient and efficient procedure for the synthesis of β‐alkyl/arylsulfanyl carbonyl compounds has been developed by a simple one‐pot reaction of dialkyl/diaryl sulfides with α,β‐unsaturated aldehydes, ketones, carboxylic esters, and nitriles in presence of indium and trimethylsilyl chloride under sonication.

  摘要 通过二烷基/二芳基硫化物与 α,β-不饱和醛、酮、羧酸酯和腈在超声处理下的铟和三甲基氯硅烷。
• ASYMMETRIC MICHAEL ADDITION OF THIOPHENOL TO MALEIC ACID ESTERS
  作者：Hiroyuki Yamashita、Teruaki Mukaiyama

  DOI：10.1246/cl.1985.363

  日期：1985.3.5

  (S)-(−)-Diisopropyl phenylthiosuccinate (81% optical purity) is prepared in 95% yield by the asymmetric Michael addition of thiophenol to diisopropyl maleate in the presence of a catalytic amount of cinchonine. The succinate thus prepared is transformed into (R)-(+)-3,4-epoxy-1-butanol without racemization.

  (S)-(-)-苯基硫代琥珀酸二异丙酯（81% 光学纯度）是在催化量的辛可宁存在下通过苯硫酚与马来酸二异丙酯的不对称迈克尔加成以 95% 的产率制备的。如此制备的琥珀酸酯在没有外消旋化的情况下转化为(R)-(+)-3,4-环氧-1-丁醇。
• Catalysis by ionic liquid: a simple, green and efficient procedure for the Michael addition of thiols and thiophosphate to conjugated alkenes in ionic liquid, [pmIm]Br
  作者：Brindaban C Ranu、Suvendu S Dey

  DOI：10.1016/j.tet.2004.03.052

  日期：2004.5

  A room temperature ionic liquid, 1-pentyl-3-methylimidazolium bromide, [pmIm]Br efficiently catalyzes Michael addition of thiols and diethyl dithiophosphate to a variety of conjugated alkenes such as alpha,beta-unsaturated carbonyl compounds, carboxylic esters, nitriles and chalcones without requiring any other organic solvent and catalyst. The ionic liquid can be recycled for subsequent reactions without any appreciable loss of efficiency. (C) 2004 Elsevier Ltd. All rights reserved.