(S)-(+)-2-(phenoxymethyl)thiirane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-(+)-2-(phenoxymethyl)thiirane
• 英文别名: (S)-(-)-2-(phenoxymethyl)thiirane；(R)-2-phenoxymethylepisulfide；(2S)-2-(phenoxymethyl)thiirane
• 化学式: C₉H₁₀OS
• 分子量: 166.244
• InChiKey: AJSVLJJVMLIBOZ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-(phenoxymethyl)thiirane 以93%的产率得到
  参考文献：
  名称：

  Gesson J. P., Jacquesy J. C., Rambaud D., Tetrahedron, 49 (1993) N 11, S 2239-2248

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氯-3-苯氧基-2-丙醇 在 chromium(VI) oxide 、 硫酸 、 水 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 27.0h， 生成 (S)-(+)-2-(phenoxymethyl)thiirane
  参考文献：
  名称：

  Asymmetric reduction of α-thiocyanatoketones by Saccharomyces cerevisiae and Mortierella isabellina—a new route to optically active thiiranes

  摘要：

  A simple method for the preparation of optically active 1-aryloxy- and 1-arylsulphanyl-3-thiocyanatopropan-2-oles from racemic 1-chloro-3-aryloxy- and 1-chloro-3-arylsulphanyl-2-propanols via 1-aryloxy- and 1-arylsulphanyl-3-thiocyanatopropan-2-ones has been developed. The enantiomerically enriched beta-hydroxythiocyanates were obtained by a microbiological reduction of the thiocyanatoketones with Saccharomyces cerevisiae or Mortierella isabellina and subsequently converted into optically active thiiranes on treatment with a lithium hydroxide solution. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.023

文献信息

• An Expeditious Synthesis of 1-Substituted and Cyclic Taurines
  作者：Jiaxi Xu、Jiaxing Huang、Fei Wang、Da-Ming Du

  DOI：10.1055/s-2005-869994

  日期：——

  A series of 1-substituted taurines, including optically active taurines, were synthesized expeditiously from epoxides via episulfidation with potassium sulfocyanate, ring-opening with dibenzylamine, followed by oxidation with performic acid, and hydrogenolysis in the presence of palladium hydroxide on carbon powder. This method was also used for the synthesis of trans-cyclic taurines.

  一系列1-取代的牛磺酸，包括光学活性牛磺酸，是由环氧化物通过硫氰酸钾环硫化、二苄胺开环、过甲酸氧化和在碳粉上氢氧化钯存在下氢解迅速合成的。该方法也用于合成反环牛磺酸。
• Chemo-enzymatic preparation of optically active thiiranes
  作者：Edyta Łukowska、Jan Plenkiewicz

  DOI：10.1016/j.tetasy.2007.01.024

  日期：2007.3

  A simple method for the preparation of optically active 2-(arylsulfanylmethyl)thiiranes and 2-(aryloxymethyl)thiiranes from the corresponding 3-thiocyanatopropan-2-ols and their acetates was developed. The starting enantiomerically enriched β-thiocyanatoalcohols and the acetates were obtained by a lipase-catalyzed hydrolysis of the appropriate racemic acetates.

  开发了一种由相应的3-硫氰酸根合丙烷-2-醇及其乙酸酯制备旋光的2-（芳基硫烷基甲基）噻喃和2-（芳氧基甲基）硫烷的简单方法。起始的对映异构体富集的β-硫氰酸根合醇和乙酸酯是通过脂肪酶催化的适当外消旋乙酸酯的水解而获得的。
• Biocatalytic Thionation of Epoxides for Enantioselective Synthesis of Thiiranes
  作者：Ran Ma、Xia Hua、Cheng‐Li He、Hui‐Hui Wang、Zhu‐Xiang Wang、Bao‐Dong Cui、Wen‐Yong Han、Yong‐Zheng Chen、Nan‐Wei Wan

  DOI：10.1002/anie.202212589

  日期：2022.12.23

  A biocatalytic thionation method is presented for the enantioselective synthesis of thiiranes from epoxides by a halohydrin dehalogenase catalyzed kinetic resolution approach using thiocyanate as a sulfur donor. Various chiral thiiranes bearing aryl and alkyl substituents were synthesized in good yields and enantioselectivities by using recombinant Escherichia coli cells expressing the engineered halohydrin

  提出了一种生物催化硫代化方法，用于使用硫氰酸盐作为硫供体，通过卤代醇脱卤酶催化的动力学拆分方法，从环氧化物中对映选择性合成硫杂环丙烷。通过使用表达工程化卤代醇脱卤素酶 HHDHapb 变体的重组大肠杆菌细胞，以良好的产率和对映体选择性合成了带有芳基和烷基取代基的各种手性硫杂环丙烷。