((2S,6S)-1-benzyl-6-methylpiperidin-2-yl)methanol | 1352966-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ((2S,6S)-1-benzyl-6-methylpiperidin-2-yl)methanol
• 英文别名: [(2S,6S)-1-benzyl-6-methylpiperidin-2-yl]methanol
• CAS: 1352966-44-9
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: PHMXMNXOLZNXDC-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  ((2S,6S)-1-benzyl-6-methylpiperidin-2-yl)methanol 在 barium hydroxide octahydrate 、 pyridine-SO3 complex 、 20% palladium hydroxide on charcoal 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 13.75h， 生成 (3R,5S,8aS)-monomorine I
  参考文献：
  名称：

  Synthesis of (−)-dihydropinidine, (2S,6R)-isosolenopsin and (+)-monomorine via a chiral synthon from l-aspartic acid

  摘要：

  The use of beta-amino aldehyde derived from L-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (-)-dihydropinidine center dot HCl, (2S,6R)-isosolenopsin center dot HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed by hydrogenation (reductive cyclization) as the key steps. CD (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.006
• 作为产物：
  描述：

  (S,E)-benzyl 1-(tert-butyldimethylsilyloxy)-6-oxohept-4-en-2-ylcarbamate 在 盐酸 、 乙醇 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 ((2S,6S)-1-benzyl-6-methylpiperidin-2-yl)methanol
  参考文献：
  名称：

  Synthesis of (−)-dihydropinidine, (2S,6R)-isosolenopsin and (+)-monomorine via a chiral synthon from l-aspartic acid

  摘要：

  The use of beta-amino aldehyde derived from L-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (-)-dihydropinidine center dot HCl, (2S,6R)-isosolenopsin center dot HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed by hydrogenation (reductive cyclization) as the key steps. CD (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.006

文献信息

• Imine-epoxide rearrangements in the formation of substituted piperidines. A stereoselective synthesis of (±) solenopsin-A.
  作者：Harry H. Wasserman、Victoria Rusiecki

  DOI：10.1016/s0040-4039(00)80657-7

  日期：1988.1

  The imine-epoxide rearrangement, followed by hydride reduction has been used to prepare substituted piperidine derivatives with control of stereochemistry. An application to the synthesis of (±) solenopsin A is reported.

  亚胺-环氧化物重排，然后氢化物还原已用于在立体化学控制下制备取代的哌啶衍生物。报道了合成（±）slenopsin A的应用。
• Synthesis of (−)-dihydropinidine, (2S,6R)-isosolenopsin and (+)-monomorine via a chiral synthon from l-aspartic acid
  作者：Chada Raji Reddy、Bellamkonda Latha

  DOI：10.1016/j.tetasy.2011.11.006

  日期：2011.11

  The use of beta-amino aldehyde derived from L-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (-)-dihydropinidine center dot HCl, (2S,6R)-isosolenopsin center dot HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed by hydrogenation (reductive cyclization) as the key steps. CD (C) 2011 Elsevier Ltd. All rights reserved.