(R)-1-[(2S)-1-[(1R)-1-phenylethyl]-2-piperidinyl]propan-2-ol | 1029020-08-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-1-[(2S)-1-[(1R)-1-phenylethyl]-2-piperidinyl]propan-2-ol
• 英文别名: (2R)-1-[(2S)-1-[(1R)-1-phenylethyl]piperidin-2-yl]propan-2-ol
• CAS: 1029020-08-3
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: ZJKIAFIATWANJA-FMKPAKJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-[(2S)-1-[(1R)-1-phenylethyl]-2-piperidinyl]propan-2-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以61%的产率得到(-)-allosedridine
  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：

  1-[(2S)-1-[(1R)-1-phenylethyl]-2-piperidinyl]-2-propanone 在 sodium tetrahydroborate 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以50%的产率得到(R)-1-[(2S)-1-[(1R)-1-phenylethyl]-2-piperidinyl]propan-2-ol
  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.