diisopropyl <(methyldithio)(methylthio)methyl>phosphonate | 141982-88-9

• 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 <(methyldithio)(methylthio)methyl>phosphonate
• 英文别名: diisopropyl methyldithiomethylthiomethylphosphonate；2-[[(Methyldisulfanyl)-methylsulfanylmethyl]-propan-2-yloxyphosphoryl]oxypropane
• CAS: 141982-88-9
• 化学式: C₉H₂₁O₃PS₃
• 分子量: 304.436
• InChiKey: XSDKIJYEPUKWKP-UHFFFAOYSA-N

物化性质

• 沸点：
  342.8±37.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  8
• 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

• 作为反应物：
  描述：

  diisopropyl <(methyldithio)(methylthio)methyl>phosphonate 、 1-氯-2-丁烯 在 lithium diisopropyl amide 作用下， 生成 diisopropyl <(crotylthio)bis(methylthio)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
• 作为产物：
  描述：

  methyl [(diisopropoxy)phosphinyl]dithioformate 在 甲胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以30%的产率得到diisopropyl <(methyldithio)(methylthio)methyl>phosphonate
  参考文献：
  名称：

  Bulpin, Andrew; Roy-Gourvennec, Sylvie Le; Masson, Serge, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 89, # 1-4, p. 119 - 132

  摘要：

  DOI：

文献信息

• Bulpin Andrew, Le Roy-Gourvennec Sylvie, Masson Serge, Phosph., Sulfur and Silicon and Relat. Elem, 89 (1994) N 1-4, S 119-132
  作者：Bulpin Andrew, Le Roy-Gourvennec Sylvie, Masson Serge

  DOI：——

  日期：——
• 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.
• Bulpin, Andrew; Roy-Gourvennec, Sylvie Le; Masson, Serge, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 89, # 1-4, p. 119 - 132
  作者：Bulpin, Andrew、Roy-Gourvennec, Sylvie Le、Masson, Serge

  DOI：——

  日期：——