diisopropyl <(ethylthio)(methyldithio)methyl>phosphonate | 141982-94-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diisopropyl <(ethylthio)(methyldithio)methyl>phosphonate
• 英文别名: 2-[[Ethylsulfanyl-(methyldisulfanyl)methyl]-propan-2-yloxyphosphoryl]oxypropane
• CAS: 141982-94-7
• 化学式: C₁₀H₂₃O₃PS₃
• 分子量: 318.463
• InChiKey: BSMAVWXSMFHDFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲硫醇 、 ethyl(diisopropoxyphosphinyl)methanedithioate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到diisopropyl <(ethylthio)(methyldithio)methyl>phosphonate
  参考文献：
  名称：

  The addition of thiols to phosphonodithioformates: reactivity of phosphorylated dithioacetal disulfides

  摘要：

  A high-yielding, thiophilic attack of thiolate ions onto phosphonodithioformates 1 led to the formation of the novel phosphorylated dithioacetal disulfides 2. Their lithiated carbanions could be both alkylated, giving access to [tris(alkylthio)methyl]phosphonates 5 via a [1,2]-Steven's type rearrangement of an intermediate sulfonium ylide D and used in Wittig-Horner reactions to give the ketene dithioacetal disulfides 7, which in turn could be cleaved by thiolate anions to the dithioesters 6. This second sequence represents a new synthesis of dithioesters starting from aldehydes with a one-carbon homologation.

  DOI：

  10.1021/jo00042a035

文献信息

• The addition of thiols to phosphonodithioformates: reactivity of phosphorylated dithioacetal disulfides
  作者：Andrew Bulpin、Serge Masson

  DOI：10.1021/jo00042a035

  日期：1992.7

  A high-yielding, thiophilic attack of thiolate ions onto phosphonodithioformates 1 led to the formation of the novel phosphorylated dithioacetal disulfides 2. Their lithiated carbanions could be both alkylated, giving access to [tris(alkylthio)methyl]phosphonates 5 via a [1,2]-Steven's type rearrangement of an intermediate sulfonium ylide D and used in Wittig-Horner reactions to give the ketene dithioacetal disulfides 7, which in turn could be cleaved by thiolate anions to the dithioesters 6. This second sequence represents a new synthesis of dithioesters starting from aldehydes with a one-carbon homologation.