1,3-benzodithiole 1-oxide | 142235-66-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,3-benzodithiole 1-oxide
• 英文别名: (R)-1,3-benzodithiole-1-oxide；(1R)-1lambda4,3-benzodithiole 1-oxide；(1R)-1λ4,3-benzodithiole 1-oxide
• CAS: 142235-66-3
• 化学式: C₇H₆OS₂
• 分子量: 170.256
• InChiKey: ZKKWOWPUYAORGR-JTQLQIEISA-N

物化性质

• 沸点：
  360.0±22.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,3-苯并二硫醇 在 Pseudomonas putida NCIMB 8859 、 氧气 作用下， 以74%的产率得到1,3-benzodithiole 1-oxide
  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

• Boyd Derek R., Sharma Narain D., Dorman James H., Dunlop Robert, Malone J+, J. Chem. Soc. Perkin Trans. 1, (1992) N 9, S 1105-1110
  作者：Boyd Derek R., Sharma Narain D., Dorman James H., Dunlop Robert, Malone J+

  DOI：——

  日期：——
• 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.