1-diethoxyphosphoryl-1-methylthio-N-ethylthioacetamide

• 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: 1-diethoxyphosphoryl-1-methylthio-N-ethylthioacetamide
• 英文别名: 2-diethoxyphosphoryl-N-ethyl-2-methylsulfanylethanethioamide
• 化学式: C₉H₂₀NO₃PS₂
• 分子量: 285.368
• InChiKey: WZXRCIMLQIRYSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对溴苯甲醛 、 1-diethoxyphosphoryl-1-methylthio-N-ethylthioacetamide 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (E)-3-(4-Bromo-phenyl)-N-ethyl-2-methylsulfanyl-thioacrylamide 、 (Z)-3-(4-Bromo-phenyl)-N-ethyl-2-methylsulfanyl-thioacrylamide
  参考文献：
  名称：

  Synthesis of 1-diethoxyphosphoryl-1-methylthio-thioacetamides and 1-methylthioethenethioamides. An unusual intramolecular α-desulfenylation of thioacetamides

  摘要：

  Addition of the lithiated alpha-phosphoryl sulfide 1-Li to alkyl or aryl isothiocyanates 4(a-f) and phenyl isocyanate 4g was found to afford 1-diethoxyphosphoryl-1-methylthio-thioacetamides 5(a-f) and -acetamide 5g, respectively. In the case of the reaction with the p-chlorophenyl isothiocyanate 4e, the alpha-desulfenylated product 6 was isolated and on the basis of P-31-NMR experiments a mechanism of its formation was proposed. The phosphonates 5(a-f), which exist in the thione form, were found to undergo the Homer-Wittig reaction with aromatic aldehydes affording 1-methylthioethenethioamides 14(a-f).

  DOI：

  10.1016/s0040-4020(01)80207-6
• 作为产物：
  描述：

  硫代甲氧基磷酸二乙酯 、 异硫氰酸乙酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到1-diethoxyphosphoryl-1-methylthio-N-ethylthioacetamide
  参考文献：
  名称：

  Synthesis of 1-diethoxyphosphoryl-1-methylthio-thioacetamides and 1-methylthioethenethioamides. An unusual intramolecular α-desulfenylation of thioacetamides

  摘要：

  Addition of the lithiated alpha-phosphoryl sulfide 1-Li to alkyl or aryl isothiocyanates 4(a-f) and phenyl isocyanate 4g was found to afford 1-diethoxyphosphoryl-1-methylthio-thioacetamides 5(a-f) and -acetamide 5g, respectively. In the case of the reaction with the p-chlorophenyl isothiocyanate 4e, the alpha-desulfenylated product 6 was isolated and on the basis of P-31-NMR experiments a mechanism of its formation was proposed. The phosphonates 5(a-f), which exist in the thione form, were found to undergo the Homer-Wittig reaction with aromatic aldehydes affording 1-methylthioethenethioamides 14(a-f).

  DOI：

  10.1016/s0040-4020(01)80207-6

文献信息

• Synthesis of 1-diethoxyphosphoryl-1-methylthio-thioacetamides and 1-methylthioethenethioamides. An unusual intramolecular α-desulfenylation of thioacetamides
  作者：Piotr Bałczewski、Piotr P Graczyk、Wiesława Perlikowska、Marian Mikołajczyk

  DOI：10.1016/s0040-4020(01)80207-6

  日期：1993.1

  Addition of the lithiated alpha-phosphoryl sulfide 1-Li to alkyl or aryl isothiocyanates 4(a-f) and phenyl isocyanate 4g was found to afford 1-diethoxyphosphoryl-1-methylthio-thioacetamides 5(a-f) and -acetamide 5g, respectively. In the case of the reaction with the p-chlorophenyl isothiocyanate 4e, the alpha-desulfenylated product 6 was isolated and on the basis of P-31-NMR experiments a mechanism of its formation was proposed. The phosphonates 5(a-f), which exist in the thione form, were found to undergo the Homer-Wittig reaction with aromatic aldehydes affording 1-methylthioethenethioamides 14(a-f).