(1-naphthalen-2-ylmethylpyrrolidin-2-yl)phosphonic acid diethyl ester | 1314238-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1-naphthalen-2-ylmethylpyrrolidin-2-yl)phosphonic acid diethyl ester
• 英文别名: diethyl (1-(naphtalen-2-ylmethyl)pyrrolidin-2-yl)phosphonate；2-Diethoxyphosphoryl-1-(naphthalen-2-ylmethyl)pyrrolidine
• CAS: 1314238-80-6
• 化学式: C₁₉H₂₆NO₃P
• 分子量: 347.394
• InChiKey: WARIBCFEDVFUKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-萘甲醛 、 diethyl phosphite 、 DL-脯氨酸 以 甲苯 为溶剂， 反应 2.0h， 以70%的产率得到(1-naphthalen-2-ylmethylpyrrolidin-2-yl)phosphonic acid diethyl ester
  参考文献：
  名称：

  A catalyst-free, three-component decarboxylative coupling of amino acids with aldehydes and H-dialkylphosphites for the synthesis of α-aminophosphonates

  摘要：

  A simple, efficient, and new method is developed for the synthesis of alpha-aminophosphonates via a three-component, catalyst-free decarboxylative coupling of amino acids with aldehydes and H-dialkyl phosphite. Treatment of amino acids with aldehydes and diethyl phosphite in the absence of catalyst, base, and ligand give alpha-aminophosphonates in moderate to good yields. This method is simple, rapid, and high-yielding. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.129

文献信息

• Copper/DIPEA-Catalyzed, Aldehyde-Induced Tandem Decarboxylation–Coupling of Natural α-Amino Acids and Phosphites or Secondary Phosphine Oxides
  作者：Dongxu Yang、Depeng Zhao、Lijuan Mao、Linqing Wang、Rui Wang

  DOI：10.1021/jo200981h

  日期：2011.8.5

  copper/DIPEA-catalyzed, aldehyde-induced intermolecular decarboxylative coupling reaction of natural α-amino acids and phosphites or secondary phosphine oxides was developed. In this process, a series of potentially useful ligands for organic synthesis and biologically important unnatural amino acid derivatives (tertiary amino phosphorus compounds) were obtained.

  开发了铜/ DIPEA催化，醛诱导的天然α-氨基酸与亚磷酸酯或仲膦氧化物的分子间脱羧偶联反应。在此过程中，获得了一系列可能有用的有机合成配体和生物学上重要的非天然氨基酸衍生物（叔氨基磷化合物）。
• A catalyst-free, three-component decarboxylative coupling of amino acids with aldehydes and H-dialkylphosphites for the synthesis of α-aminophosphonates
  作者：Babak Kaboudin、Leila Karami、Jun-ya Kato、Hiroshi Aoyama、Tsutomu Yokomatsu

  DOI：10.1016/j.tetlet.2013.06.129

  日期：2013.9

  A simple, efficient, and new method is developed for the synthesis of alpha-aminophosphonates via a three-component, catalyst-free decarboxylative coupling of amino acids with aldehydes and H-dialkyl phosphite. Treatment of amino acids with aldehydes and diethyl phosphite in the absence of catalyst, base, and ligand give alpha-aminophosphonates in moderate to good yields. This method is simple, rapid, and high-yielding. (C) 2013 Elsevier Ltd. All rights reserved.