1-(tert-butyldithio)-1-(methylthio)-3-methylbutene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(tert-butyldithio)-1-(methylthio)-3-methylbutene
• 英文别名: (E)-1-(tert-butyldisulfanyl)-3-methyl-1-methylsulfanylbut-1-ene
• 化学式: C₁₀H₂₀S₃
• 分子量: 236.467
• InChiKey: XKXOLVJOALTSEE-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(tert-butyldithio)-1-(methylthio)-3-methylbutene 在 水 、 lithium methanethiolate 作用下， 生成 3-methyl-dithiobutyric acid methyl ester
  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
• 作为产物：
  描述：

  diisopropyl <(tert-butyldithio)(methylthio)methyl>phosphonate 、 异丁醛 在 lithium diisopropyl amide 作用下， 生成 3-methyl-dithiobutyric acid methyl ester 、 1-(tert-butyldithio)-1-(methylthio)-3-methylbutene
  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.