{[Benzyl-(2-chloro-acetyl)-amino]-phenyl-methyl}-phosphonic acid diethyl ester | 159852-13-8

• 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: {[Benzyl-(2-chloro-acetyl)-amino]-phenyl-methyl}-phosphonic acid diethyl ester
• 英文别名: N-benzyl-2-chloro-N-[diethoxyphosphoryl(phenyl)methyl]acetamide
• CAS: 159852-13-8
• 化学式: C₂₀H₂₅ClNO₄P
• 分子量: 409.85
• InChiKey: UXCVYZLGWFQNEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {[Benzyl-(2-chloro-acetyl)-amino]-phenyl-methyl}-phosphonic acid diethyl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (1-Benzyl-4-oxo-2-phenyl-azetidin-2-yl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of 4-phosphono-β-lactams via phosphite addition to acyliminium salts

  摘要：

  4-Aryl-4-phosphono-beta-lactams are prepared by acylation of iminium salts with chloroacetyl chloride followed by phosphite addition and ring closure using sodium hydride as a base. Deacylation of the iminium salt is in competition with the desired addition of phosphites to acyliminium salts, which lowers the yield of the reaction. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00005-4
• 作为产物：
  描述：

  (E)-N-benzylidenebenzylamine 以 四氢呋喃 为溶剂， 反应 2.17h， 生成 {[Benzyl-(2-chloro-acetyl)-amino]-phenyl-methyl}-phosphonic acid diethyl ester
  参考文献：
  名称：

  One-Pot Synthesis ofN-Chloroacetyl 1-Aminoalkyl Phosphonates - Precursors of 4-Phosphono-β-Lactams

  摘要：

  4-膦酰基-β-内酰胺通过三步序列合成，其中包括通过磷稳定的碳负离子形成C3-C4键。氯化前体可以通过两种不同方法合成：一种是将芳香亚胺进行N-酰化，然后加入三烷基亚磷酸酯或通过先对合适亚胺进行膦酰化再进行独立反应步骤中的N-酰化。前者方法更受欢迎，因为反应简便且产率高。

  DOI：

  10.1055/s-2005-918440

文献信息

• A Simple, Convenient and General Method for the Synthesis of<i>N</i>-Acylalkylaminomethyl-and<i>N</i>-Acylalkylamino(alkyl, aryl, heteroaryl)methylphosphonates and -phosphine Oxides
  作者：Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1055/s-1994-25612

  日期：——

  A variety of N-acylalkylaminomethyl- and alkylamino(alkyl, aryl, heteroaryl)methylphosphonates and -phosphine oxides has been efficiently prepared by acylation of suitable Schiff bases and subsequent treatment of the chloromethylcarboxamide intermediates with the appropriate phosphorylating agent.

  通过适当的Schiff碱的酰化反应，以及随后用适当的磷酸化试剂处理氯甲基羧酰胺中间体，高效制备了多种N-酰基烷基氨基甲基和烷基氨基（烷基、芳基、杂芳基）甲基磷酸酯和磷酸氧化物。
• One-Pot Synthesis of<i>N</i>-Chloroacetyl 1-Aminoalkyl Phosphonates - Precursors of 4-Phosphono-β-Lactams
  作者：Christian V. Stevens、Kristof Moonen

  DOI：10.1055/s-2005-918440

  日期：——

  4-Phosphono-β-lactams are synthesized via a three-step sequence, including final formation of the C3-C4 bond through a phosphorus-stabilized carbanion. The chlorinated precursors can be synthesized via two different methods: a one-pot N-acylation of an aromatic imine followed by addition of a trialkyl phosphite or phosphonylation of a suitable imine followed by N-acylation in a separate reaction step. The former method was preferred because of the ease of the reaction and the good yields obtained.

  4-膦酰基-β-内酰胺通过三步序列合成，其中包括通过磷稳定的碳负离子形成C3-C4键。氯化前体可以通过两种不同方法合成：一种是将芳香亚胺进行N-酰化，然后加入三烷基亚磷酸酯或通过先对合适亚胺进行膦酰化再进行独立反应步骤中的N-酰化。前者方法更受欢迎，因为反应简便且产率高。
• Synthesis of 4-phosphono-β-lactams via phosphite addition to acyliminium salts
  作者：Christian V. Stevens、Wannes Vekemans、Kristof Moonen、Thomas Rammeloo

  DOI：10.1016/s0040-4039(03)00005-4

  日期：2003.2

  4-Aryl-4-phosphono-beta-lactams are prepared by acylation of iminium salts with chloroacetyl chloride followed by phosphite addition and ring closure using sodium hydride as a base. Deacylation of the iminium salt is in competition with the desired addition of phosphites to acyliminium salts, which lowers the yield of the reaction. (C) 2003 Elsevier Science Ltd. All rights reserved.