diisopropyl phosphonate | 141982-96-9

• 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 phosphonate
• 英文别名: diisopryl (mercapto-methylthio-methyl)phosphonate；Di(propan-2-yloxy)phosphoryl-methylsulfanylmethanethiol
• CAS: 141982-96-9
• 化学式: C₈H₁₉O₃PS₂
• 分子量: 258.343
• InChiKey: NTXAUPDEOKMTRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diisopropyl phosphonate 以67%的产率得到
  参考文献：
  名称：

  Makomo Hubert, Masson Serge, Saquet Monique, Tetrahedron, 50 (1994) N 34, S 10277-10288

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl [(diisopropoxy)phosphinyl]dithioformate 在 lithium (diisopropylamino)borohydride 、 盐酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 diisopropyl phosphonate
  参考文献：
  名称：

  Reductions of phosphonodithioformates: Syntheses of β-phosphonyl thiols and hemidithioacetals.

  摘要：

  The phosphonodithioformates appeared versatile precursors to the (mercaptomethyl)phosphonates and derivatives, through sodium borohydride reduction in acetonitrile heated under reflux. By contrast, when the reduction was performed at room temperature with sodium borohydride, the (mercapto-alkylthio-methyl)phosphonates were exclusively obtained; reduction with BH3-Me(2)S (BMS) or within lithium diisopropylaminoborohydride also led to these hemidithioacetals. The aforementioned products of reduction were characterized by the syntheses of various derivatives. In particular, S-phosphonyl trithiocarbonates, N-phenyl imidodithiocarbonate and dithiocarbamate were prepared.

  DOI：

  10.1016/s0040-4020(01)81760-9

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.
• Makomo Hubert, Masson Serge, Saquet Monique, Tetrahedron, 50 (1994) N 34, S 10277-10288
  作者：Makomo Hubert, Masson Serge, Saquet Monique

  DOI：——

  日期：——
• Reductions of phosphonodithioformates: Syntheses of β-phosphonyl thiols and hemidithioacetals.
  作者：Hubert Makomo、Serge Masson、Monique Saquet

  DOI：10.1016/s0040-4020(01)81760-9

  日期：1994.8

  The phosphonodithioformates appeared versatile precursors to the (mercaptomethyl)phosphonates and derivatives, through sodium borohydride reduction in acetonitrile heated under reflux. By contrast, when the reduction was performed at room temperature with sodium borohydride, the (mercapto-alkylthio-methyl)phosphonates were exclusively obtained; reduction with BH3-Me(2)S (BMS) or within lithium diisopropylaminoborohydride also led to these hemidithioacetals. The aforementioned products of reduction were characterized by the syntheses of various derivatives. In particular, S-phosphonyl trithiocarbonates, N-phenyl imidodithiocarbonate and dithiocarbamate were prepared.