十二烷硫酸,S-乙基酯 | 100962-82-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 十二烷硫酸,S-乙基酯
• 英文名称: ethyl dodecanethionate
• 英文别名: ethyl thiolaurate；thiolauric acid S-ethyl ester；Thiolaurinsaeure-S-aethylester；Monothiolaurinsaeure-S-ethylester；S-ethyl dodecanethioate
• CAS: 100962-82-1
• 化学式: C₁₄H₂₈OS
• 分子量: 244.442
• InChiKey: YWSJXUZHMJMYKL-UHFFFAOYSA-N

物化性质

• 沸点：
  116-118 °C(Press: 1 Torr)
• 密度：
  0.902±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  十二烷硫酸,S-乙基酯 在 hydrophobic polystyrene-supported sulfonic acid 水 作用下， 反应 36.0h， 以93%的产率得到月桂酸
  参考文献：
  名称：

  Hydrophobic Polymer-Supported Catalyst for Organic Reactions in Water:  Acid-Catalyzed Hydrolysis of Thioesters and Transprotection of Thiols

  摘要：

  A hydrophobic polystyrene-supported sulfonic acid was found to be effective for hydrolysis of thioesters in pure water. It was revealed that the catalyst was much superior to other Bronsted acid catalysts. Transprotection of thiols from thioesters to thioethers has been successfully performed in water using this catalytic system.

  DOI：

  10.1021/ol026906m
• 作为产物：
  描述：

  月桂酰氯 、 乙硫醇 在 iron(III) chloride hexahydrate 作用下， 以 neat (no solvent) 为溶剂， 以99 %的产率得到十二烷硫酸,S-乙基酯
  参考文献：
  名称：

  以 FeCl3 为非均相催化剂的（硫）酯衍生物的无溶剂合成

  摘要：

  报道了一种在室温下从简单的酰氯合成 (硫) 酯的简单、无溶剂的方法。简单的 FeCl 3 (5 mol%) 能够以高选择性轻松、接近完全地转化等摩尔起始材料。已经证明了催化剂的回收。

  DOI：

  10.1016/j.tetlet.2023.154524

文献信息

• From carboxylic acids to the trifluoromethyl group using BrF3
  作者：Or Cohen、Eyal Mishani、Shlomo Rozen

  DOI：10.1016/j.tet.2010.03.045

  日期：2010.5

  Organic trifluoromethyl derivatives were made from aromatic and aliphatic carboxylic acids by transforming them first into the corresponding dithioesters followed by reaction with bromine trifluoride under mild conditions (0 degrees C, 2 min). (C) 2010 Elsevier Ltd. All rights reserved.
• Thiol Ester−Boronic Acid Cross-Coupling. Catalysis Using Alkylative Activation of the Palladium Thiolate Intermediate
  作者：Cecile Savarin、Jiri Srogl、Lanny S. Liebeskind

  DOI：10.1021/ol000231a

  日期：2000.10.1

  [GRAPHICS]Thiol esters and boronic acids do not participate in cross-coupling in the presence of palladium catalysts. However, efficient palladium-catalyzed thiol ester-boronic acid cross-coupling is observed when simple alkylating agents are present. Alkylative conversion of the very stable palladium-thiolate bond to a labile palladium-thioether bond is presumed to be crucial to the catalysis. Of the systems studied, 4-halo-nbutyl thiol esters were most effective in this cross-coupling.
• Bestmann,H.J. et al., Chemische Berichte, 1966, vol. 99, p. 1906 - 1911
  作者：Bestmann,H.J. et al.

  DOI：——

  日期：——
• Ralston; Segebrecht; Bauer, Journal of Organic Chemistry, 1939, vol. 4, p. 503,504
  作者：Ralston、Segebrecht、Bauer

  DOI：——

  日期：——
• Ester Interchange Reactions of Long Chain Thiol Esters¹
  作者：GEORGE S. SASIN、PAUL R. SCHAEFFER、RICHARD SASIN

  DOI：10.1021/jo01361a013

  日期：1957.10