S-[5-benzoylsulfanyl-2-(1,3-dithiol-2-ylidene)-1,3-dithiol-4-yl] benzenecarbothioate | 157496-94-1

• 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: S-[5-benzoylsulfanyl-2-(1,3-dithiol-2-ylidene)-1,3-dithiol-4-yl] benzenecarbothioate
• CAS: 157496-94-1
• 化学式: C₂₀H₁₂O₂S₆
• 分子量: 476.71
• InChiKey: BXVDNCQZEFZJRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  溴丙烷 、 S-[5-benzoylsulfanyl-2-(1,3-dithiol-2-ylidene)-1,3-dithiol-4-yl] benzenecarbothioate 在 sodium ethanolate 作用下， 生成 4,5-Bis-propylsulfanyl-[2,2']bi[[1,3]dithiolylidene]
  参考文献：
  名称：

  2-(Triphenylphosphonio)-4,5-bis(thiobenzoyl)-1,3-dithiole Tetrafluoroborate: A Versatile Wittig Reagent for the Synthesis of Unsymmetrical Tetrathiafulvalenes and 1,3-Dithiol-2-ylidene Derivatives

  摘要：

  The title Wittig reagent 5 has been prepared in three steps (84% overall yield) from 4,5-bis(benzoylthio)-1,3-dithiole-2-thione. Reactions of ylide 7, generated by treatment of 5 with diisopropylethylamine at room temperature, have been exploited in the synthesis of new unsymmetrical tetrathiafulvalenes and 1,3-dithiol-2-ylidene derivatives. Subsequent removal of the benzoyl protecting group with sodium ethoxide liberates the transient TTF-dithiolate or 1,3-dithiole-dithiolate anions which can be alkylated in situ. The X-ray crystal structures of compounds 17 and 18 are reported: close nonbonded S-O intramolecular interactions are observed in both structures.

  DOI：

  10.1021/jo00097a038
• 作为产物：
  描述：

  S-(5-benzoylsulfanyl-2-methylsulfanyl-1,3-dithiol-4-yl) benzenecarbothioate 在 tetrafluoroboric acid 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 0.58h， 生成 S-[5-benzoylsulfanyl-2-(1,3-dithiol-2-ylidene)-1,3-dithiol-4-yl] benzenecarbothioate
  参考文献：
  名称：

  2-(Triphenylphosphonio)-4,5-bis(thiobenzoyl)-1,3-dithiole Tetrafluoroborate: A Versatile Wittig Reagent for the Synthesis of Unsymmetrical Tetrathiafulvalenes and 1,3-Dithiol-2-ylidene Derivatives

  摘要：

  The title Wittig reagent 5 has been prepared in three steps (84% overall yield) from 4,5-bis(benzoylthio)-1,3-dithiole-2-thione. Reactions of ylide 7, generated by treatment of 5 with diisopropylethylamine at room temperature, have been exploited in the synthesis of new unsymmetrical tetrathiafulvalenes and 1,3-dithiol-2-ylidene derivatives. Subsequent removal of the benzoyl protecting group with sodium ethoxide liberates the transient TTF-dithiolate or 1,3-dithiole-dithiolate anions which can be alkylated in situ. The X-ray crystal structures of compounds 17 and 18 are reported: close nonbonded S-O intramolecular interactions are observed in both structures.

  DOI：

  10.1021/jo00097a038

文献信息

• 2-(Triphenylphosphonio)-4,5-bis(thiobenzoyl)-1,3-dithiole Tetrafluoroborate: A Versatile Wittig Reagent for the Synthesis of Unsymmetrical Tetrathiafulvalenes and 1,3-Dithiol-2-ylidene Derivatives
  作者：Thomas K. Hansen、Martin R. Bryce、Judith A. K. Howard、Dimitri S. Yufit

  DOI：10.1021/jo00097a038

  日期：1994.9

  The title Wittig reagent 5 has been prepared in three steps (84% overall yield) from 4,5-bis(benzoylthio)-1,3-dithiole-2-thione. Reactions of ylide 7, generated by treatment of 5 with diisopropylethylamine at room temperature, have been exploited in the synthesis of new unsymmetrical tetrathiafulvalenes and 1,3-dithiol-2-ylidene derivatives. Subsequent removal of the benzoyl protecting group with sodium ethoxide liberates the transient TTF-dithiolate or 1,3-dithiole-dithiolate anions which can be alkylated in situ. The X-ray crystal structures of compounds 17 and 18 are reported: close nonbonded S-O intramolecular interactions are observed in both structures.