(R)-(-)-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: (R)-(-)-2-(phenoxymethyl)thiirane
• 英文别名: (S)-2-phenoxymethylepisulfide；(2R)-2-(phenoxymethyl)thiirane
• 化学式: C₉H₁₀OS
• 分子量: 166.244
• InChiKey: AJSVLJJVMLIBOZ-SECBINFHSA-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 (R)-(-)-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。