(S,S)-(+)-bis(2-phenyl-2-chloroethyl)sulfide | 340168-19-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (S,S)-(+)-bis(2-phenyl-2-chloroethyl)sulfide
• 英文别名: [(1S)-1-chloro-2-[(2S)-2-chloro-2-phenylethyl]sulfanylethyl]benzene
• CAS: 340168-19-6
• 化学式: C₁₆H₁₆Cl₂S
• 分子量: 311.275
• InChiKey: MGLBJPXSLJNFAG-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S,S)-(+)-bis(2-phenyl-2-chloroethyl)sulfide 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到rac-bis-1,2-(ethylsulfanyl)-1-phenylethane
  参考文献：
  名称：

  Synthesis of C 2 -symmetric tris-thioethers via optically active mustards

  摘要：

  Chiral dihydroxy thioethers derived from L-mandelic and L-lactic acid are activated with SOCl2, SOBr2 and by bis-trifluoroacetate formation to give optically active mustard gas analogues. These compounds serve as substrates for stereospecific nucleophilic substitution reactions with NaSEt and NaSPh to furnish C-2-symmetric tris-thioethers with overall inversion of configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00006-0
• 作为产物：
  描述：

  (S)-2-((S)-2-Hydroxy-2-phenyl-ethylsulfanyl)-1-phenyl-ethanol 在 氯化亚砜 作用下， 反应 2.0h， 以94%的产率得到(S,S)-(+)-bis(2-phenyl-2-chloroethyl)sulfide
  参考文献：
  名称：

  Synthesis of C 2 -symmetric tris-thioethers via optically active mustards

  摘要：

  Chiral dihydroxy thioethers derived from L-mandelic and L-lactic acid are activated with SOCl2, SOBr2 and by bis-trifluoroacetate formation to give optically active mustard gas analogues. These compounds serve as substrates for stereospecific nucleophilic substitution reactions with NaSEt and NaSPh to furnish C-2-symmetric tris-thioethers with overall inversion of configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00006-0

文献信息

• Synthesis of C 2 -symmetric tris-thioethers via optically active mustards
  作者：Jens Christoffers、Ulrich Rößler

  DOI：10.1016/s0040-4020(01)00006-0

  日期：2001.2

  Chiral dihydroxy thioethers derived from L-mandelic and L-lactic acid are activated with SOCl2, SOBr2 and by bis-trifluoroacetate formation to give optically active mustard gas analogues. These compounds serve as substrates for stereospecific nucleophilic substitution reactions with NaSEt and NaSPh to furnish C-2-symmetric tris-thioethers with overall inversion of configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.