4-[diethoxyphosphoryl(hydroxy)methyl]-N,N-dimethylbenzenecarbothioamide | 134360-21-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 4-[diethoxyphosphoryl(hydroxy)methyl]-N,N-dimethylbenzenecarbothioamide
• CAS: 134360-21-7
• 化学式: C₁₄H₂₂NO₄PS
• 分子量: 331.373
• InChiKey: RTSCWBGBJDPIHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[diethoxyphosphoryl(hydroxy)methyl]-N,N-dimethylbenzenecarbothioamide 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到Methanesulfonic acid (diethoxy-phosphoryl)-(4-dimethylthiocarbamoyl-phenyl)-methyl ester
  参考文献：
  名称：

  Variable electronic properties of the CSNMe2 thioamide group

  摘要：

  The sigma-I value for the CSNMe2 group has been determined and the value of 0.23 indicates that this group is inductively electron withdrawing. The effect of the p-CSNMe2 group on the solvolysis rate of cumyl chloride has also been determined and, relative to the p-H analogue, this group has a negligible effect on rate. p-CSNMe2 substitution slows the hydrolysis rate of substituted benzaldehyde dimethyl acetals. p-CSNMe2 substitution enhances the solvolysis rate of ArCH(OMs)PO(OEt)2. These variable rate effects on reactions involving cationic intermediates have been interpreted in terms of variable electronic properties of the CSNMe2 group. This group can be cation stabilizing, electroneutral, or cation destabilizing, depending on the charge demands of specific cations. This is a result of a conjugative interaction of CSNMe2 with a cationic center and resultant delocalization of positive charge onto sulfur. The importance of such conjugation is a function of the amount of transition-state charge developed on the carbon bearing the CSNMe2 group. The electronic effects of the amphielectronic p-CSNMe2 group are compared to the more conventional effects of CONMe2 and the m-CSNMe2 analogues.

  DOI：

  10.1021/jo00013a038
• 作为产物：
  描述：

  4-溴苯甲醛二甲缩醛 在 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 42.33h， 生成 4-[diethoxyphosphoryl(hydroxy)methyl]-N,N-dimethylbenzenecarbothioamide
  参考文献：
  名称：

  Variable electronic properties of the CSNMe2 thioamide group

  摘要：

  The sigma-I value for the CSNMe2 group has been determined and the value of 0.23 indicates that this group is inductively electron withdrawing. The effect of the p-CSNMe2 group on the solvolysis rate of cumyl chloride has also been determined and, relative to the p-H analogue, this group has a negligible effect on rate. p-CSNMe2 substitution slows the hydrolysis rate of substituted benzaldehyde dimethyl acetals. p-CSNMe2 substitution enhances the solvolysis rate of ArCH(OMs)PO(OEt)2. These variable rate effects on reactions involving cationic intermediates have been interpreted in terms of variable electronic properties of the CSNMe2 group. This group can be cation stabilizing, electroneutral, or cation destabilizing, depending on the charge demands of specific cations. This is a result of a conjugative interaction of CSNMe2 with a cationic center and resultant delocalization of positive charge onto sulfur. The importance of such conjugation is a function of the amount of transition-state charge developed on the carbon bearing the CSNMe2 group. The electronic effects of the amphielectronic p-CSNMe2 group are compared to the more conventional effects of CONMe2 and the m-CSNMe2 analogues.

  DOI：

  10.1021/jo00013a038