(1R)-[(3S)-methylsulfinyl]methylphenyl sulfoxide | 670271-13-3

• 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: (1R)-[(3S)-methylsulfinyl]methylphenyl sulfoxide
• 英文别名: [(R)-[(S)-methylsulfinyl]methylsulfinyl]benzene
• CAS: 670271-13-3
• 化学式: C₈H₁₀O₂S₂
• 分子量: 202.298
• InChiKey: ZZWLCVCAPDDSEQ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R)-[(3S)-methylsulfinyl]methylphenyl sulfoxide 在 [ReOCl₃(PPh₃)₂] 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (+)-(S)-(methylsulfanylmethyl) phenyl sulfoxide 、 (R)-(methylsulfanylmethyl)phenyl sulfoxide
  参考文献：
  名称：

  Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides

  摘要：

  Toluene- and naphthalene-dioxygenase-catalysed oxidation of six bicyclic disulfide substrates, using whole cells of Pseudomonas putida, gave the corresponding monosulfoxides with high ee values and enantiocomplementarity, in most cases. Two alcohol-sulfoxide diastereoisomers, formed from the reaction of the (R)-1,3-benzodithiole-1-oxide metabolite with n-butyllithium and benzaldehyde, were separated and stereochemically assigned. Treatment, of enantiopure (1R,3R)-benzo-1,3-dithiole-1,3-dioxide, obtained by chemoenzymatic synthesis, with alkyllithium reagents, resulted in a novel ring-opening reaction which proceeded with inversion of configuration to yield a series of acyclic disulfoxides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.107
• 作为产物：
  描述：

  1,3-benzodithiole 1-oxide 在 sodium periodate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 24.0h， 生成 (1R)-[(3S)-methylsulfinyl]methylphenyl sulfoxide
  参考文献：
  名称：

  Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides

  摘要：

  Toluene- and naphthalene-dioxygenase-catalysed oxidation of six bicyclic disulfide substrates, using whole cells of Pseudomonas putida, gave the corresponding monosulfoxides with high ee values and enantiocomplementarity, in most cases. Two alcohol-sulfoxide diastereoisomers, formed from the reaction of the (R)-1,3-benzodithiole-1-oxide metabolite with n-butyllithium and benzaldehyde, were separated and stereochemically assigned. Treatment, of enantiopure (1R,3R)-benzo-1,3-dithiole-1,3-dioxide, obtained by chemoenzymatic synthesis, with alkyllithium reagents, resulted in a novel ring-opening reaction which proceeded with inversion of configuration to yield a series of acyclic disulfoxides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.107

文献信息

• Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides
  作者：Derek R Boyd、Narain D Sharma、Simon A Haughey、Martina A Kennedy、John F Malone、Steven D Shepherd、Christopher C.R Allen、Howard Dalton

  DOI：10.1016/j.tet.2003.10.107

  日期：2004.1

  Toluene- and naphthalene-dioxygenase-catalysed oxidation of six bicyclic disulfide substrates, using whole cells of Pseudomonas putida, gave the corresponding monosulfoxides with high ee values and enantiocomplementarity, in most cases. Two alcohol-sulfoxide diastereoisomers, formed from the reaction of the (R)-1,3-benzodithiole-1-oxide metabolite with n-butyllithium and benzaldehyde, were separated and stereochemically assigned. Treatment, of enantiopure (1R,3R)-benzo-1,3-dithiole-1,3-dioxide, obtained by chemoenzymatic synthesis, with alkyllithium reagents, resulted in a novel ring-opening reaction which proceeded with inversion of configuration to yield a series of acyclic disulfoxides. (C) 2003 Elsevier Ltd. All rights reserved.