(S)-2-(3-nitrophenylaminomethyl)pyrrolidine | 1399801-71-8

• 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: (S)-2-(3-nitrophenylaminomethyl)pyrrolidine
• 英文别名: 3-nitro-N-[[(2S)-pyrrolidin-2-yl]methyl]aniline
• CAS: 1399801-71-8
• 化学式: C₁₁H₁₅N₃O₂
• 分子量: 221.259
• InChiKey: FRRWHFGHTRIJRU-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  67.2
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (S)-N-(3-nitrophenyl)pyrrolidine-2-carboxamide 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到(S)-2-(3-nitrophenylaminomethyl)pyrrolidine
  参考文献：
  名称：

  Chiral amine catalyzed enantio- and diastereoselective Michael reaction in brine

  摘要：

  Simple pyrrolidine-based chiral amines were synthesized and used for the Michael addition of different ketones to a variety of nitro-olefins in brine. The effect of different surfactants and acids on the yields and stereochemical outcome of the Michael adducts was studied in detail. Chiral amine 1g was found to catalyze the formation of Michael adducts with high enantioselectivity (up to >99%), diastereoselectivity [up to 98:2 (syn:anti)] and yield (up to 94%). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.026

文献信息

• Chiral amine catalyzed enantio- and diastereoselective Michael reaction in brine
  作者：Sarbjit Singh、Swapandeep Singh Chimni

  DOI：10.1016/j.tetasy.2012.06.026

  日期：2012.7

  Simple pyrrolidine-based chiral amines were synthesized and used for the Michael addition of different ketones to a variety of nitro-olefins in brine. The effect of different surfactants and acids on the yields and stereochemical outcome of the Michael adducts was studied in detail. Chiral amine 1g was found to catalyze the formation of Michael adducts with high enantioselectivity (up to >99%), diastereoselectivity [up to 98:2 (syn:anti)] and yield (up to 94%). (C) 2012 Elsevier Ltd. All rights reserved.