(4-phenylpiperazin-1-yl)-[(2S)-pyrrolidin-2-yl]methanone | 1217850-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (4-phenylpiperazin-1-yl)-[(2S)-pyrrolidin-2-yl]methanone
• CAS: 1217850-37-7
• 化学式: C₁₅H₂₁N₃O
• 分子量: 259.351
• InChiKey: IMBNVEKXERUTFC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-phenylpiperazin-1-yl)-[(2S)-pyrrolidin-2-yl]methanone 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到(S)-1-phenyl-4-(pyrrolidin-2-ylmethyl)piperazine
  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
• 作为产物：
  描述：

  在 sodium carbonate 作用下， 以 三氯乙烷 为溶剂， 生成 (4-phenylpiperazin-1-yl)-[(2S)-pyrrolidin-2-yl]methanone
  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.