(1R,2R,3S,6S)-(-)-2-[2-[1,3]-dioxolan-2-yl-ethyl]-3-ethyl-1-(1-phenyl-2-hydroxyethyl)-6-propylpiperidine | 213014-69-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (1R,2R,3S,6S)-(-)-2-[2-[1,3]-dioxolan-2-yl-ethyl]-3-ethyl-1-(1-phenyl-2-hydroxyethyl)-6-propylpiperidine
• 英文别名: (2R)-2-[(2R,3S,6S)-2-[2-(1,3-dioxolan-2-yl)ethyl]-3-ethyl-6-propylpiperidin-1-yl]-2-phenylethanol
• CAS: 213014-69-8
• 化学式: C₂₃H₃₇NO₃
• 分子量: 375.552
• InChiKey: KLBRIRZNLYPWTB-UVUJQTEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,6S)-(-)-2-[2-[1,3]-dioxolan-2-yl-ethyl]-3-ethyl-1-(1-phenyl-2-hydroxyethyl)-6-propylpiperidine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 盐酸 、 乙醇 、 乙酸乙酯 为溶剂， 以73%的产率得到(5S,8S,8aR)-(+)-8-ethyl-5-propyl-octahydroindolizidine hydrochloride
  参考文献：
  名称：

  A short enantioselective access to 2,3,6-trialkylpiperidines and 5,8-dialkylindolizidines

  摘要：

  An enantioselective access to 2,3,6-trialkylpiperidines 5 is described. This sequence is illustrated by the four-step syntheses, from salts 1, of piperidine 6 and indolizidines 7 and 8. The overall yields are in the range 10-15%. The stereochemistry of intermediates is discussed, supported by two X-ray studies, and comparison with analogs. Stereochemical properties of intermediate oxazolidine derivatives 4 were used to orient the syntheses towards different diastereoisomers such as 7 or 8. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00566-3
• 作为产物：
  描述：

  (3R,8aS)-(-)-6-ethyl-3-phenyl-3,7,8,8a-tetrahydro-2H-oxazolo<3,2-a>pyridine 在 magnesium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (1R,2R,3S,6S)-(-)-2-[2-[1,3]-dioxolan-2-yl-ethyl]-3-ethyl-1-(1-phenyl-2-hydroxyethyl)-6-propylpiperidine
  参考文献：
  名称：

  A short enantioselective access to 2,3,6-trialkylpiperidines and 5,8-dialkylindolizidines

  摘要：

  An enantioselective access to 2,3,6-trialkylpiperidines 5 is described. This sequence is illustrated by the four-step syntheses, from salts 1, of piperidine 6 and indolizidines 7 and 8. The overall yields are in the range 10-15%. The stereochemistry of intermediates is discussed, supported by two X-ray studies, and comparison with analogs. Stereochemical properties of intermediate oxazolidine derivatives 4 were used to orient the syntheses towards different diastereoisomers such as 7 or 8. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00566-3

文献信息

• A short enantioselective access to 2,3,6-trialkylpiperidines and 5,8-dialkylindolizidines
  作者：Yung-Sing Wong、Dino Gnecco、Christian Marazano、Angèle Chiaroni、Claude Riche、Annick Billion、Bhupesh C. Das

  DOI：10.1016/s0040-4020(98)00566-3

  日期：1998.8

  An enantioselective access to 2,3,6-trialkylpiperidines 5 is described. This sequence is illustrated by the four-step syntheses, from salts 1, of piperidine 6 and indolizidines 7 and 8. The overall yields are in the range 10-15%. The stereochemistry of intermediates is discussed, supported by two X-ray studies, and comparison with analogs. Stereochemical properties of intermediate oxazolidine derivatives 4 were used to orient the syntheses towards different diastereoisomers such as 7 or 8. (C) 1998 Elsevier Science Ltd. All rights reserved.