N-甲氧基-N-甲基(2S)-1-[(1R)-1-苯基乙基]哌啶-2-乙酰胺 | 1029019-93-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-甲氧基-N-甲基(2S)-1-[(1R)-1-苯基乙基]哌啶-2-乙酰胺
• 英文名称: N-methoxy-N-methyl (2S)-1-[(1R)-1-phenylethyl]piperidine-2-acetamide
• 英文别名: N-methoxy-N-methyl-2-[(2S)-1-[(1R)-1-phenylethyl]piperidin-2-yl]acetamide
• CAS: 1029019-93-9
• 化学式: C₁₇H₂₆N₂O₂
• 分子量: 290.406
• InChiKey: WIICKLDGSRWZJL-ZBFHGGJFSA-N

物化性质

• 沸点：
  369.0±34.0 °C(predicted)
• 密度：
  1.058±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲氧基-N-甲基(2S)-1-[(1R)-1-苯基乙基]哌啶-2-乙酰胺 、 乙基氯化镁 以 四氢呋喃 为溶剂， 反应 1.5h， 以94%的产率得到1-[(2S)-1-[(1R)-1-苯基乙基]-2-哌啶基]-2-丁酮
  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
• 作为产物：
  描述：

  tert-butyl N-(7-[methoxy(methyl)amino]-7-oxo-(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， 以64%的产率得到N-甲氧基-N-甲基(2S)-1-[(1R)-1-苯基乙基]哌啶-2-乙酰胺
  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.