diethyl(p-tolylcarbamoyl)phosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl(p-tolylcarbamoyl)phosphonate
• 英文别名: 1-diethoxyphosphoryl-N-(4-methylphenyl)formamide
• 化学式: C₁₂H₁₈NO₄P
• 分子量: 271.253
• InChiKey: UZCDFTPBBBHFKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  diethyl (4-methylbenzoyl)phosphonate 以11%的产率得到
  参考文献：
  名称：

  Sprecher Milon, Kost Daniel, J. Amer. Chem. Soc, 116 (1994) N 3, S 1016-1026

  摘要：

  DOI：

文献信息

• Iodine-Promoted Rapid Construction of Carbamoylphosphonates from Phosphinecarboxamides
  作者：Yong-Hui Wu、Qiu-Li Wu、Wen-Peng Wang、Xi-Cun Wang、Zheng-Jun Quan

  DOI：10.1002/adsc.201800303

  日期：2018.6.15

  one‐step, I2‐promoted P−H phosphorylation and oxygenation of phosphinecarboxamides to give carbamoylphosphonates was achieved. This transformation exhibits exceptional substrate generality and functional group compatibility and affords good to excellent yields of the desired phosphonates. Notably, cyclic carbamoylphosphonates can be obtained from diols. The mechanism was investigated using IR, 1H and 31P

  一步实现了I 2促进膦膦酰胺的P-H磷酸化和氧合，生成氨基甲酰基膦酸酯。该转化表现出优异的底物通用性和官能团相容性，并提供所需膦酸酯的良好至优异的产率。值得注意的是，环状氨基甲酰基膦酸酯可以从二醇获得。使用IR，1 H和31 P NMR光谱研究了该机理。
• The Schmidt Reaction of Dialkyl Acylphosphonates
  作者：Milon Sprecher、Daniel Kost

  DOI：10.1021/ja00082a024

  日期：1994.2

  The scope of the Schmidt rearrangement of ketones has been extended to dialkyl acylphosphonates (11a-111). Surprisingly, it was found that 11a-11dand 11g, in which the acyl moiety was benzoyl alone or benzoyl bearing an electron-attracting or mildly electron-releasing substituent, yielded an overwhelming portion of products resulting from C-to-N migration of the aryl group (N-arylcarbamoylphosphonates

  酮的施密特重排的范围已扩展到酰基膦酸二烷基酯 (11a-111)。令人惊讶的是，发现 11a-11d 和 11g，其中酰基部分是单独的苯甲酰基或带有吸电子或轻度放电子取代基的苯甲酰基，产生了绝大多数由芳基的 C 到 N 迁移产生的产物组（N-芳基氨基甲酰基膦酸酯，12 和 N-芳基甲酰胺，15）。相反，带有强大的电子释放对烷氧基的芳烃羰基膦酸酯产生由膦酸酯基团从 C 迁移到 N 或消除的产物（N-芳烃羰基磷酰胺二烷基酯，13 和芳烃甲腈，分别为 17）
• Electrochemically driven P–H oxidation and functionalization: synthesis of carbamoylphosphonates from phosphoramides and alcohols
  作者：Qiu-Li Wu、Xing-Guo Chen、Cong-De Huo、Xi-Cun Wang、Zheng-Jun Quan

  DOI：10.1039/c8nj05739g

  日期：——

  An electrochemical method to achieve carbamoylphosphonates from phosphoramides and alcohols via P–H oxidation and functionalization by using n-Bu4NI as a catalyst is reported. A series of carbamoylphosphonates were obtained with good to excellent yields under mild reaction conditions. The electrochemical reaction is carried out under constant current electrolysis, with the alcohol being used as a solvent

  据报道，使用n -Bu 4 NI作为催化剂，通过PH氧化和官能化反应，可从磷酰胺和醇中获得氨基甲酰基膦酸酯的电化学方法。在温和的反应条件下，以良好或优异的收率获得了一系列氨基甲酰基膦酸酯。电化学反应在恒定电流电解下进行，其中醇用作溶剂和底物，并且是有吸引力的绿色合成方法。