Acetyl-aethyldisulfid | 5824-50-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: Acetyl-aethyldisulfid
• 英文别名: S-propylsulfanyl ethanethioate
• CAS: 5824-50-0
• 化学式: C₅H₁₀OS₂
• 分子量: 150.266
• InChiKey: BFPCLVZPAUQKOY-UHFFFAOYSA-N

物化性质

• 沸点：
  219.9±23.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetyl-aethyldisulfid 、 S-(4-fluorophenyl) 4-methylbenzenesulfonothioate 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.18h， 以61%的产率得到1-(4-fluorophenyl)-3-propyltrisulfane
  参考文献：
  名称：

  Unsymmetrical Organotrisulfide Formation via Low-Temperature Disulfanyl Anion Transfer to an Organothiosulfonate

  摘要：

  New methodology is presented for the formation of unsymmetrical organotrisulfides in a high yield and purity, relatively free of polysulfide byproducts. The highlight of the method is the low-temperature (-78 degrees C) deprotection of a disulfanyl acetate with sodium methoxide in THF to form a disulfanyl anion, which reacts rapidly in situ with an organothiosulfonate (S-aryl or S-alkyl) within 30 seconds followed by quenching. The discovery of these new reaction conditions together with the relative greenness of the chemistry overall makes for an efficient protocol, from which a range of organotrisulfides covering aliphatic, aromatic, as well as cysteine and sugar groups can be accessed in a high yield and purity.

  DOI：

  10.1021/acs.joc.8b03262
• 作为产物：
  描述：

  toluene-4-thiosulfonic acid S-propyl ester 、 potassium thioacetate 以 二氯甲烷 为溶剂， 生成 Acetyl-aethyldisulfid
  参考文献：
  名称：

  Unsymmetrical Organotrisulfide Formation via Low-Temperature Disulfanyl Anion Transfer to an Organothiosulfonate

  摘要：

  New methodology is presented for the formation of unsymmetrical organotrisulfides in a high yield and purity, relatively free of polysulfide byproducts. The highlight of the method is the low-temperature (-78 degrees C) deprotection of a disulfanyl acetate with sodium methoxide in THF to form a disulfanyl anion, which reacts rapidly in situ with an organothiosulfonate (S-aryl or S-alkyl) within 30 seconds followed by quenching. The discovery of these new reaction conditions together with the relative greenness of the chemistry overall makes for an efficient protocol, from which a range of organotrisulfides covering aliphatic, aromatic, as well as cysteine and sugar groups can be accessed in a high yield and purity.

  DOI：

  10.1021/acs.joc.8b03262

文献信息

• Organic disulfides and related substances. 32. Preparation and decomposition of .beta.-substituted ethyl acetyl disulfides
  作者：Lamar Field、Wayne S. Hanley、Ilda McVeigh

  DOI：10.1021/jo00818a002

  日期：1971.9
• Unsymmetrical Organotrisulfide Formation via Low-Temperature Disulfanyl Anion Transfer to an Organothiosulfonate
  作者：Doaa Ali、Roger Hunter、Catherine H. Kaschula、Stephen De Doncker、Sophie C. M. Rees-Jones

  DOI：10.1021/acs.joc.8b03262

  日期：2019.3.1

  New methodology is presented for the formation of unsymmetrical organotrisulfides in a high yield and purity, relatively free of polysulfide byproducts. The highlight of the method is the low-temperature (-78 degrees C) deprotection of a disulfanyl acetate with sodium methoxide in THF to form a disulfanyl anion, which reacts rapidly in situ with an organothiosulfonate (S-aryl or S-alkyl) within 30 seconds followed by quenching. The discovery of these new reaction conditions together with the relative greenness of the chemistry overall makes for an efficient protocol, from which a range of organotrisulfides covering aliphatic, aromatic, as well as cysteine and sugar groups can be accessed in a high yield and purity.