α-((2S)-1-((R)-1-phenylethyl)-2-piperidinyl)acetophenone | 1029020-03-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-((2S)-1-((R)-1-phenylethyl)-2-piperidinyl)acetophenone
• 英文别名: 1-phenyl-2-[(2S)-1-[(1R)-1-phenylethyl]piperidin-2-yl]ethanone
• CAS: 1029020-03-8
• 化学式: C₂₁H₂₅NO
• 分子量: 307.436
• InChiKey: KJOJQKYOEJVWRV-XLIONFOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl N-(7-oxo-7-phenyl-(E)-5-heptenyl)-N-[(R)-(1-phenylethyl)]carbamate 在 三氟乙酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 α-((2R)-1-((R)-1-phenylethyl)-2-piperidinyl)acetophenone 、 α-((2S)-1-((R)-1-phenylethyl)-2-piperidinyl)acetophenone
  参考文献：
  名称：

  Asymmetric aza-Michael addition: synthesis of (−)-allosedridine and (−)-2-epi-ethylnorlobelol

  摘要：

  The combination of cross-metathesis and aza-Michael addition is an efficient method for generating piperidine alkaloids. Allosedridine and 2-epi-ethylnorlobelol were synthesized in six steps with ca. 25% overall yield. The aza-Michael addition is reversible for phenyl and alkyl ketones; however, the epimerization is not observed for the corresponding ester and amide. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.019

文献信息

• Asymmetric aza-Michael addition: synthesis of (−)-allosedridine and (−)-2-epi-ethylnorlobelol
  作者：Li-Ju Chen、Duen-Ren Hou

  DOI：10.1016/j.tetasy.2008.02.019

  日期：2008.4

  The combination of cross-metathesis and aza-Michael addition is an efficient method for generating piperidine alkaloids. Allosedridine and 2-epi-ethylnorlobelol were synthesized in six steps with ca. 25% overall yield. The aza-Michael addition is reversible for phenyl and alkyl ketones; however, the epimerization is not observed for the corresponding ester and amide. (c) 2008 Elsevier Ltd. All rights reserved.