diisopropyl <(bis-methylthio)methyl>phosphonate | 126181-61-1

• 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 <(bis-methylthio)methyl>phosphonate
• 英文别名: 2-[bis(methylsulfanyl)methyl-propan-2-yloxyphosphoryl]oxypropane
• CAS: 126181-61-1
• 化学式: C₉H₂₁O₃PS₂
• 分子量: 272.37
• InChiKey: JAIBDTKSNNUHOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  15.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  methyl [(diisopropoxy)phosphinyl]dithioformate 在 lithium (diisopropylamino)borohydride 、 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 44.0h， 生成 diisopropyl <(bis-methylthio)methyl>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 use of phosphonodithioformates for the synthesis of ketene dithioacetals
  作者：Andrew Bulpin、Serge Masson、Aboubacary Sene

  DOI：10.1016/s0040-4039(00)99259-1

  日期：1989.1

  Phosphonodithioformates 1 undergo thiophilic addition with both organolithium and Grignard reagents to give metallated dithioacetals of formyl-phosphonates 2, available for protonation, alkylation or use in Wittig-Horner reactions. Oxidation of 1 by meta-chloroperbenzoic acid leads to the corresponding sulphine 4 equally suitable for thiophilic addition.

  磷二硫代甲酸酯1与有机锂和格利雅试剂均进行巯基加成，生成甲酰基膦酸酯2的金属化二硫缩醛，可用于质子化，烷基化或用于Wittig-Horner反应。间氯过苯甲酸氧化1会生成同样适合硫代加成反应的相应的硫4。
• BULPIN, ANDREW;MASSON, SERGE;SENE, ABOUBACARY, TETRAHEDRON LETT., 30,(1989) N6, C. 3415-3418
  作者：BULPIN, ANDREW、MASSON, SERGE、SENE, ABOUBACARY

  DOI：——

  日期：——
• 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.