(S)-4-(1-[(R)-1-phehyl-2-hydroxyethyl]piperidin-2-yl)butanol | 1043392-03-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (S)-4-(1-[(R)-1-phehyl-2-hydroxyethyl]piperidin-2-yl)butanol
• 英文别名: 4-[(2S)-1-[(1R)-2-hydroxy-1-phenylethyl]piperidin-2-yl]butan-1-ol
• CAS: 1043392-03-5
• 化学式: C₁₇H₂₇NO₂
• 分子量: 277.407
• InChiKey: QLZKYUCDROSUTQ-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-(1-[(R)-1-phehyl-2-hydroxyethyl]piperidin-2-yl)butanol 、 二碳酸二叔丁酯 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以83%的产率得到(S)-4-(1-(tert-butoxycarbonyl)piperidin-2-yl)butanol
  参考文献：
  名称：

  Enantioselective synthesis of (S)-1,6,7,8,9,9a-hexahydroquinolizin-4-one. Formal synthesis of the lycopodium alkaloids senepodine G and cermizine C

  摘要：

  The synthesis of the title compound, a key intermediate in the synthesis of some lycopodium and lupin alkaloids, is reported. From a stereochemical standpoint the key steps are the stereoselective cyclocondensation of ketodiester 1 with (R)-phenylglycinol and the stereocontrolled reduction, with retention of configuration, of the oxazolidine ring in the resulting oxazolopiperidone lactam 2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.022
• 作为产物：
  描述：

  methyl 4-[(3R,8aR)-5-oxo-3-phenyl-3,6,7,8-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridin-8a-yl]butanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以68%的产率得到(S)-4-(1-[(R)-1-phehyl-2-hydroxyethyl]piperidin-2-yl)butanol
  参考文献：
  名称：

  Enantioselective synthesis of (S)-1,6,7,8,9,9a-hexahydroquinolizin-4-one. Formal synthesis of the lycopodium alkaloids senepodine G and cermizine C

  摘要：

  The synthesis of the title compound, a key intermediate in the synthesis of some lycopodium and lupin alkaloids, is reported. From a stereochemical standpoint the key steps are the stereoselective cyclocondensation of ketodiester 1 with (R)-phenylglycinol and the stereocontrolled reduction, with retention of configuration, of the oxazolidine ring in the resulting oxazolopiperidone lactam 2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.022

文献信息

• Enantioselective synthesis of (S)-1,6,7,8,9,9a-hexahydroquinolizin-4-one. Formal synthesis of the lycopodium alkaloids senepodine G and cermizine C
  作者：Mercedes Amat、Rosa Griera、Robert Fabregat、Joan Bosch

  DOI：10.1016/j.tetasy.2008.04.022

  日期：2008.5

  The synthesis of the title compound, a key intermediate in the synthesis of some lycopodium and lupin alkaloids, is reported. From a stereochemical standpoint the key steps are the stereoselective cyclocondensation of ketodiester 1 with (R)-phenylglycinol and the stereocontrolled reduction, with retention of configuration, of the oxazolidine ring in the resulting oxazolopiperidone lactam 2. (C) 2008 Elsevier Ltd. All rights reserved.