dimethyl N-methyl-N-2-methylphenylphosphoramidate | 25626-90-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: dimethyl N-methyl-N-2-methylphenylphosphoramidate
• 英文别名: dimethyl N-methyl-N-(2-tolyl)-phosphoramide；N-dimethoxyphosphoryl-N,2-dimethylaniline
• CAS: 25626-90-8
• 化学式: C₁₀H₁₆NO₃P
• 分子量: 229.216
• InChiKey: OKJUNVZYSWIXAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl N-methyl-N-2-methylphenylphosphoramidate 在 silica gel 作用下， 以 苯 为溶剂， 生成 dimethyl N-(o-tolyl)phosphoramidate
  参考文献：
  名称：

  用三价磷试剂还原亚硝基化合物。第五部分。亚磷酸三烷基酯还原烷基和甲氧基硝基苯以及硝基苯

  摘要：

  三乙基-和三甲基-亚磷酸酯用的反应ö， -米- ，和p硝基甲苯，ö -和p -ethylnitrobenzene，ö -和p -nitroanisole，和硝基苯得到二烷基相应Ñ -arylphosphoramidates，和二烷基Ñ -烷基N-芳基膦酸酯，以及在某些情况下，三烷基N-芳基膦酸酯，可能是上述酰胺化物的前体。在某些情况下，形成了3 H-氮杂庚基-7-基膦酸二烷基烷基酯的低产率（约18％），这表明亚硝基物质是中间产物。亚磷酸三乙酯与对-乙基，对-甲基和对甲氧基硝基苯以及亚磷酸三甲酯与邻-硝基苯甲醚和对硝基甲苯的收率低，这是记录的第一个记录的简单实例，该例子是简单的芳族硝基被未活化的取代电子影响或特殊的空间因素。

  DOI：

  10.1039/j39690002813
• 作为产物：
  描述：

  Trimethyl-N-o-tolyl-phosphorimidat 生成 dimethyl N-methyl-N-2-methylphenylphosphoramidate
  参考文献：
  名称：

  Electronic and steric effects in arylphosphoramidates and phosphorimidates as monitored by carbon-13 nuclear magnetic resonance

  摘要：

  Abstract13C NMR chemical shifts and 13C31P couplings are reported for ten arylphosphoramidates and five arylphoshorimidates. The para‐carbon chemical shifts in the phosphoramidates are interpreted in terms of substantial nitrogen lone pair delocalization into the aromatic ring, a phenomenon which is subject to steric inhibition of resonance. By contrast, in the phosphorimidates the electron release into the phenyl ring is not attenuated by steric congestion. Conformational changes about the arylN bond in all compounds have been monitored by vicinal 31PNC13C couplings.

  DOI：

  10.1002/mrc.1270140618

文献信息

• Reduction of nitro- and nitroso-compounds by tervalent phosphorus reagents. Part V. Reduction of alkyl- and methoxy-nitrobenzenes, and nitrobenzene by trialkyl phosphites
  作者：J. I. G. Cadogan、D. J. Sears、D. M. Smith、M. J. Todd

  DOI：10.1039/j39690002813

  日期：——

  In some cases low (⩽18%) yields of dialkyl alkyl-3H-azepin-7-ylphosphonates are formed, indicating the intermediacy of nitrenoid species. Reaction of triethyl phosphite with p-ethyl-, p-methyl-, and p-methoxynitrobenzenes, and of trimethyl phosphite with o-nitroanisole and p-nitrotoluene give low yields of the corresponding dialkyl arylphosphonates, representing the first recorded instances of displacement

  三乙基-和三甲基-亚磷酸酯用的反应ö， -米- ，和p硝基甲苯，ö -和p -ethylnitrobenzene，ö -和p -nitroanisole，和硝基苯得到二烷基相应Ñ -arylphosphoramidates，和二烷基Ñ -烷基N-芳基膦酸酯，以及在某些情况下，三烷基N-芳基膦酸酯，可能是上述酰胺化物的前体。在某些情况下，形成了3 H-氮杂庚基-7-基膦酸二烷基烷基酯的低产率（约18％），这表明亚硝基物质是中间产物。亚磷酸三乙酯与对-乙基，对-甲基和对甲氧基硝基苯以及亚磷酸三甲酯与邻-硝基苯甲醚和对硝基甲苯的收率低，这是记录的第一个记录的简单实例，该例子是简单的芳族硝基被未活化的取代电子影响或特殊的空间因素。
• Electronic and steric effects in arylphosphoramidates and phosphorimidates as monitored by carbon-13 nuclear magnetic resonance
  作者：G. W. Buchanan、F. G. Morin

  DOI：10.1002/mrc.1270140618

  日期：1980.12

  Abstract13C NMR chemical shifts and 13C31P couplings are reported for ten arylphosphoramidates and five arylphoshorimidates. The para‐carbon chemical shifts in the phosphoramidates are interpreted in terms of substantial nitrogen lone pair delocalization into the aromatic ring, a phenomenon which is subject to steric inhibition of resonance. By contrast, in the phosphorimidates the electron release into the phenyl ring is not attenuated by steric congestion. Conformational changes about the arylN bond in all compounds have been monitored by vicinal 31PNC13C couplings.