bis{(S)-2-hydroxy-2-phenylethyl} disulfide | 649884-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis{(S)-2-hydroxy-2-phenylethyl} disulfide
• 英文别名: bis[(S)-2-hydroxy-2-phenylethyl]disulfide
• CAS: 649884-96-8
• 化学式: C₁₆H₁₈O₂S₂
• 分子量: 306.45
• InChiKey: VUYDNDKAMALDBG-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  bis{(S)-2-hydroxy-2-phenylethyl} disulfide 在 六甲基磷酰三胺 、 正丁基锂 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-1-methoxy-2-(3,3-dimethyl-1-butynylsulfinyl)-1-phenylethane
  参考文献：
  名称：

  Synthesis of chiral vinylic sulfoxides by Pd-catalyzed asymmetric sulfinylzincation

  摘要：

  Novel asymmetric sulfinylzincation of alkynoates has been accomplished via a Pd-catalyzed sulfinylzincation using 1-alkynyl sulfoxides bearing chiral auxiliaries as a sulfinylating reagent. The reaction proceeded in a highly syn-selective fashion, giving the (E)-beta-sulfinyl alpha,beta-unsaturated ester exclusively. Among the chiral sulfinylating reagents tested, an isoborneol-type compound (Rs)-4 showed the best results in terms of both yield and diastereoselectivity. As a result of optimization of the reaction, the selectivity was improved up to 92:8 dr, and stereochemistry of the newly formed sulfur stereogenic center was revealed as (Ss)-configuration. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.037
• 作为产物：
  描述：

  (S)-环氧苯乙烷 在 双(三甲基硫化硅) 、 四丁基氟化铵 、 aluminum oxide 、 sodium iodate 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 26.0h， 生成 bis{(S)-2-hydroxy-2-phenylethyl} disulfide
  参考文献：
  名称：

  Equilibrium shift induced by chiral nanoparticle precipitation in rhodium-catalyzed disulfide exchange reaction

  摘要：

  Chiral silica (P)-nanoparticles grafted with (P)-helicene recognize the molecular structure of a chiral diol disulfide in the presence of monool disulfide and dibutyl disulfide. The (P)-nanoparticles selectively adsorb the diol disulfide, aggregate, and precipitate from solution. Under rhodium-catalyzed equilibrium among three disulfides, the diol disulfide is removed from solution by precipitation, which induces an equilibrium shift in the solution. By conducting the precipitation experiment twice, we obtained the dial disulfide in 37% yield from a statistical 1:2:1 equilibrium mixture of three disulfides. The method is applied to a racemic monool disulfide, and an optically active dial disulfide is obtained via kinetic resolution and equilibrium shift. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.106