diethyl (2-pyrrolidinmethyl)phosphonate | 1248426-34-7

• 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 (2-pyrrolidinmethyl)phosphonate
• 英文别名: (2S)-2-(diethoxyphosphorylmethyl)pyrrolidine
• CAS: 1248426-34-7
• 化学式: C₉H₂₀NO₃P
• 分子量: 221.236
• InChiKey: JKZNJTVJBOTYTK-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  6
• 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：

  Boc-L-脯氨酸甲酯 在 盐酸 、 偶氮二异丁腈 、 水 、 三正丁基氢锡 、 高氯酸,吡啶 、 二异丁基氢化铝 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 8.0h， 生成 diethyl (2-pyrrolidinmethyl)phosphonate
  参考文献：
  名称：

  Synthesis of phosphonic analog of (S)-homoproline

  摘要：

  DOI：

  10.1134/s1070363214010289
• 作为试剂：
  描述：

  反式硝基苯乙烯 、 丙酮 在 diethyl (2-pyrrolidinmethyl)phosphonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (4S)-5-nitro-4-phenylpentan-2-one 、 (R)-5-nitro-4-phenylpentan-2-one
  参考文献：
  名称：

  Novel cyclic β-aminophosphonate derivatives as efficient organocatalysts for the asymmetric Michael addition reactions of ketones to nitrostyrenes

  摘要：

  Three novel catalysts based upon cyclic beta-aminophosphonate derivatives 1-3 were designed to catalyze the asymmetric Michael addition reactions of ketones to p-nitrostyrenes. Among the catalysts that have been prepared in this study, cyclic beta-aminophosphonic acid monoethylester 3 showed the highest catalytic ability, giving the corresponding Michael adduct in good yields, high enantioselectivities (up to 92% ee), and high diastereoselectivities (syn:anti up to 95:5). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.049

文献信息

• Novel cyclic β-aminophosphonate derivatives as efficient organocatalysts for the asymmetric Michael addition reactions of ketones to nitrostyrenes
  作者：Triana Widianti、Yoshikazu Hiraga、Satoshi Kojima、Manabu Abe

  DOI：10.1016/j.tetasy.2010.05.049

  日期：2010.8

  Three novel catalysts based upon cyclic beta-aminophosphonate derivatives 1-3 were designed to catalyze the asymmetric Michael addition reactions of ketones to p-nitrostyrenes. Among the catalysts that have been prepared in this study, cyclic beta-aminophosphonic acid monoethylester 3 showed the highest catalytic ability, giving the corresponding Michael adduct in good yields, high enantioselectivities (up to 92% ee), and high diastereoselectivities (syn:anti up to 95:5). (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of phosphonic analog of (S)-homoproline
  作者：O. O. Kolodyazhnaya、A. O. Kolodyazhnaya、O. I. Kolodyazhnyi

  DOI：10.1134/s1070363214010289

  日期：2014.1