(1SR,2SR)-1-methyl-2-phenylthiocyclohexanol

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1SR,2SR)-1-methyl-2-phenylthiocyclohexanol
• 英文别名: t-2-Thiophenoxy-1-methyl-r-cyclohexanol；(1R,2R)-1-methyl-2-phenylsulfanylcyclohexan-1-ol
• 化学式: C₁₃H₁₈OS
• 分子量: 222.351
• InChiKey: GREVWVDVWMTKIA-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1SR,2SR)-1-methyl-2-phenylthiocyclohexanol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 1-methyl-6-phenylthiocyclohex-1-ene
  参考文献：
  名称：

  Dehydration of alcohols with an adjacent phenylthio (PhS) group

  摘要：

  DOI：

  10.1016/s0040-4039(00)98638-6
• 作为产物：
  描述：

  3-甲基-1-环己烯 在 indium(III) chloride 硫酸 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 水 为溶剂， 反应 0.05h， 生成 (1SR,2SR)-1-methyl-2-phenylthiocyclohexanol
  参考文献：
  名称：

  Thiolysis of Alkyl- and Aryl-1,2-epoxides in Water Catalyzed by InCl3

  摘要：

  The pH dependence of thiolysis of 1,2-epoxides with thiophenol in water and the influence of a Lewis acid catalyst is investigated. InCl3 showed a very high efficiency in catalyzing this process at pH 4.0. The regloselectivity of the nucleophilic attack is markedly influenced going from pH 9.0 to pH 4.0. A one-pot procedure running solely in water to prepare trans-2-(phenylsulphinyl)cyclohexan-1-ol is reported starting from epoxycyclohexane, via thiolysis reaction and oxidation with t-butyl hydroperoxide.

  DOI：

  10.1002/1615-4169(200206)344:3/4<379::aid-adsc379>3.0.co;2-4

文献信息

• ZnCl₂as an Efficient Catalyst in the Thiolysis of 1,2-Epoxides by Thiophenol in Aqueous Medium
  作者：Ferdinando Pizzo、Luigi Vaccaro、David Amantini、Francesco Fringuelli、Simone Tortoioli

  DOI：10.1055/s-2003-42107

  日期：——

  ZnCl2 (5 mol%) is an efficient catalyst for the thiolysis of 1,2-epoxides by thiophenol in water at pH 4.0. A variety of β-hydroxy phenylsulfides were obtained in short reaction times and excellent yields. Starting from cyclohexene oxide (1), two one-pot multi-step procedures in sole water (thiolysis/oxidation with H2O2) have been realized, for the chemoselective synthesis of the corresponding β-hydroxysulfoxides 19 or for the related β-hydroxysulfone 20.

  ZnCl2（5 mol%）是一种有效的催化剂，用于在pH 4.0的水相中通过硫苯醇对1,2-环氧化物进行硫解反应。在短反应时间内获得了多种β-羟基苯硫醚，并且产率非常高。从环己烯氧化物（1）出发，已经实现了在纯水中进行的两步一锅法（硫解/用H2O2氧化），用于选择性合成相应的β-羟基亚砜19或相关的β-羟基磺酰20。
• Tetrathiomolybdate Assisted Epoxide Ring Opening with Masked Thiolates and Selenoates:  Multistep Reactions in One Pot
  作者：Naduthambi Devan、Perali Ramu Sridhar、Kandikere Ramaiah Prabhu、Srinivasan Chandrasekaran

  DOI：10.1021/jo0263418

  日期：2002.12.1

  Tetrathiomolybdate provides an easy access to beta-hydroxy disulfides, beta-hydroxy sulfides, and selenides from epoxides in a tandem, multistep process in one pot. This strategy has been utilized effectively in the construction of thiabicylo[3.2.2]nonane derivative 24.

  四硫代钼酸盐可在一锅中通过多步串联过程轻松获得环氧化物中的β-羟基二硫化物，β-羟基硫化物和硒化物。该策略已被有效地用于构建噻菌基[3.2.2]壬烷衍生物24。
• Organic reactions at alumina surfaces. Mild and selective opening of epoxides by alcohols, thiols, benzeneselenol, amines, and acetic acid
  作者：Gary H. Posner、D. Z. Rogers

  DOI：10.1021/ja00467a014

  日期：1977.12
• Zn(II)-Catalyzed Thiolysis of Oxiranes in Water under Neutral Conditions
  作者：Francesco Fringuelli、Ferdinando Pizzo、Simone Tortoioli、Luigi Vaccaro

  DOI：10.1021/jo0348266

  日期：2003.10.1

  Thiolysis of a variety of 1,2-epoxides in water at 30degreesC and pH 7.0 is strongly accelerated by ZnCl(2) (10 mol %) except when amino- and carboxythiophenol are used. The aqueous medium and the catalyst were recovered and reused in various runs without affecting the efficiency of the process.
• Borax-catalyzed thiolysis of 1,2-epoxides in aqueous medium
  作者：Peng Gao、Peng-Fei Xu、Hongbin Zhai

  DOI：10.1016/j.tetlet.2008.09.004

  日期：2008.11

  A convenient, economical, and practical protocol for borax-catalyzed thiolysis of 1,2-epoxides in aqueous medium has been developed, which has greatly expanded the utility scope of borax in organic synthesis. (C) 2008 Elsevier Ltd. All rights reserved.