diethyl 1-(propylamino)cyclohexylphosphonate

• 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: diethyl 1-(propylamino)cyclohexylphosphonate
• 英文别名: 1-diethoxyphosphoryl-N-propylcyclohexan-1-amine
• 化学式: C₁₃H₂₈NO₃P
• 分子量: 277.344
• InChiKey: OXUZNVSNWFMRHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正丙胺 、 二乙基亚磷酸氢酯 、 环己酮 在 silica gel 作用下， 反应 0.08h， 以87%的产率得到diethyl 1-(propylamino)cyclohexylphosphonate
  参考文献：
  名称：

  Microwave-assisted One-pot Synthesis of α-Amino Phosphonates via Three Component Coupling on a Silica Gel Support

  摘要：

  通过醛和酮与胺的一锅反应，开发出一种在微波辐照下使用硅胶支撑试剂合成 α-氨基膦酸盐的快速、高效、通用程序。

  DOI：

  10.1246/cl.2005.1042

文献信息

• Tween-20: An Efficient Catalyst for One-Pot Synthesis of α-Aminophosphonates in Aqueous Media
  作者：Ch. Syama Sundar、D. Srinivasulu、S. K. Nayak、C. Suresh Reddy

  DOI：10.1080/10426507.2011.631641

  日期：2012.4.1

  A green one-pot three-component synthesis has been developed for alpha-aminophosphonates by condensation of aldehydes, amines, and diethylphosphite by using nonionic surfactant Tween-20 as catalyst in aqueous media. The results showed that this synthetic route for alpha-aminophosphonates takes just 25-60 min for completion at 60 degrees C and affords 64%-91% yields depending on the nature of the amine substrates. The major advantages of this novel method are green reaction conditions with water as solvent, simple workup, less reaction times, and high to moderate yields.
• Bismuth(III) Chloride–Catalyzed Three‐Component Coupling: Synthesis of α‐Amino Phosphonates
  作者：Zhuang‐Ping Zhan、Jun‐Ping Li

  DOI：10.1080/00397910500212692

  日期：2005.10

  A simple and efficient method has been developed for the one-pot synthesis of alpha-amino phosphonates from the reaction of a carbonyl compound, amine, and dialkyl phosphite. The highly catalytic nature of bismuth(III) chloride and the fact that it is relatively nontoxic, low cost, easy to handle, and insensitive to small amounts of air and moisture make this method especially attractive for large-scale synthesis.