1-(4-chlorophenylsulfanyl)octan-2-ol

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(4-chlorophenylsulfanyl)octan-2-ol
• 英文别名: 1-(4-chlorophenylthio)octan-2-ol；gwx-913；1-(4-Chlorophenyl)sulfanyloctan-2-ol
• 化学式: C₁₄H₂₁ClOS
• mdl: MFCD24743854
• 分子量: 272.839
• InChiKey: QEBWAZONTFGWHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4'-二氯二苯二硫醚 、 1,2-环氧辛烷 在 rongalite 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以86%的产率得到1-(4-chlorophenylsulfanyl)octan-2-ol
  参考文献：
  名称：

  Tandem base-free synthesis of β-hydroxy sulphides under ultrasound irradiation

  摘要：

  Rongalite® 可促进二芳基二硫化物的裂解，在原位生成相应的硫代硫酸盐，然后在超声波辐照下以区域选择性的方式对环氧化物进行简便的开环反应，从而以良好到极佳的收率生成 β-羟基硫化物。这种方法的重要特点是无碱、无味、产率高、反应速度快、操作简单、高区域选择性、成本效益高，而且不需要过渡金属催化剂。值得注意的是，在标准条件下，1,2-二苯基二硒烷与 2-（苯氧基甲基）环氧乙烷的开环反应也能顺利进行，并以极好的收率得到 β-羟基硒化物。

  DOI：

  10.1007/s12039-012-0305-6

文献信息

• Indium(I) iodide promoted cleavage of dialkyl disulfides — Application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides
  作者：Brindaban C Ranu、Tanmay Mandal

  DOI：10.1139/v06-065

  日期：2006.5.1

  promotes cleavage of dialkyl disulfides generating thiolate anions that then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters, and nitriles under neutral conditions producing corresponding β-ketosulfides or β-cyanosulfides. This strategy has also been used for the regioselective nucleophilic ring opening of epoxides by thiolate anions in presence of indium(III) chloride producing

  碘化铟 (I) 促进二烷基二硫化物的裂解，生成硫醇阴离子，然后在中性条件下轻松加成到 α,β-不饱和酮、醛、羧酸酯和腈，产生相应的 β-酮硫化物或 β-氰基硫化物。该策略也已用于在氯化铟 (III) 存在下通过硫醇阴离子对环氧化物进行区域选择性亲核开环，产生相应的 β-羟基苯基硫化物。反应通常非常干净、产率高且相当快。因此，利用这种裂解反应开发了合成 β-酮硫化物或 β-氰基硫化物和 β-羟烷基硫化物的简便方法。环氧化物，β-羟基硫化物。
• Ionic Liquid Promoted Regio- and Stereo-Selective Thiolysis of Epoxides—A Simple and Green Approach to β-Hydroxy- and β-Keto Sulfides
  作者：Brindaban C. Ranu、Tanmay Mandal、Subhash Banerjee、Suvendu S. Dey

  DOI：10.1071/ch06434

  日期：——

  A variety of epoxides underwent facile cleavage by thiols under the catalysis of 1-methyl-3-butylimidazolium bromide, [bmIm]Br, to produce the corresponding β-hydroxy sulfides with high regio- and stereo-selectivity. On the other hand, a specially designed basic ionic liquid, [bmIm]OH, efficiently catalyzes the thiolysis of α,β-epoxy ketones providing β-keto sulfides through simultaneous retro-aldol cleavages. The reactions are clean, high yielding, and do not require any organic solvent. The catalyst is also recycled.

  在 1-甲基-3-丁基溴化咪唑鎓（[bmIm]Br）的催化下，多种环氧化物很容易被硫醇裂解，从而以高区域和立体选择性生成相应的 β-羟基硫化物。另一方面，一种特殊设计的碱性离子液体 [bmIm]OH 可高效催化 α,β-环氧酮的硫解反应，通过同时发生的逆醛裂解提供 β-酮硫化物。该反应清洁、产率高，且不需要任何有机溶剂。催化剂也可回收利用。
• Three-Component Oxychalcogenation of Alkenes under Metal-Free Conditions: A Tetrabutylammonium Tribromide-Catalyzed System
  作者：Jiawei Huang、Xiaoman Li、Liang Xu、Yu Wei

  DOI：10.1021/acs.joc.2c02856

  日期：2023.3.3

  A three-component oxychalcogenation reaction, from alkenes, diselenides/thiophenols, and H2O/alcohols, has been realized herein. Tetrabutylammonium tribromide (TBATB) and dimethylsulfoxide (DMSO) are utilized as the catalyst and the terminal oxidant, respectively, to enable this difunctionalization transformation. The metal-free reaction system shows good functional group compatibility, providing a

  本文实现了烯烃、二硒化物/苯硫酚和 H 2 O/醇的三组分氧硫属化反应。四丁基三溴化铵 (TBATB) 和二甲基亚砜 (DMSO) 分别用作催化剂和末端氧化剂，以实现这种双官能化转化。无金属反应体系显示出良好的官能团相容性，为获得β-羟基或β-烷氧基有机硫族化合物提供了统一实用的途径。
• Rongalite® promoted highly regioselective synthesis of β-hydroxy sulfides by ring opening of epoxides with disulfides
  作者：Wenxue Guo、Jiuxi Chen、Dengze Wu、Jinchang Ding、Fan Chen、Huayue Wu

  DOI：10.1016/j.tet.2009.04.085

  日期：2009.7

  Rongaliteo (R) promotes cleavage of disulfides generating thiolate anions that then undergo facile ring opening of epoxides in the presence of K2CO3 to afford alpha-addition products 3 with good to excellent yields. The important features of this methodology are broad substrates scope, high yielding, reasonably rapid reaction rate, high regioselectivity and no requirement of metal catalysts. It should be noted that the thiolate anion attacks the epoxides derived from styrene to produce the corresponding alpha-addition products 3 with high regioselectivity, instead of the beta-addition regioisomer 4 that Could be formed from the attack of the nucleophile at the benzylic position. (C) 2009 Elsevier Ltd. All rights reserved.