(4R,9aS)-9a-benzyl-4-phenylhexahydropyrido[2,1-c][1,4]oxazin-1-one | 158221-60-4

• 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: (4R,9aS)-9a-benzyl-4-phenylhexahydropyrido[2,1-c][1,4]oxazin-1-one
• 英文别名: (4R,9aR)-9a-Benzyl-4-phenylhexahydropyrido<2,1-c><1,4>oxazin-1-one；(4R,9aR)-9a-benzyl-4-phenyl-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,4]oxazin-1-one
• CAS: 158221-60-4
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: BAUAMYLUJPLHKB-PZJWPPBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,9aS)-9a-benzyl-4-phenylhexahydropyrido[2,1-c][1,4]oxazin-1-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 1.0h， 以70%的产率得到(R)-2-Benzyl-2-piperidinecarboxylic acid
  参考文献：
  名称：

  Asymmetric Synthesis. 32. A New Access to Enantiomerically Pure (S)-(-)-Pipecolic Acid and 2- or 6-Alkylated Derivatives

  摘要：

  Enantiomerically pure (S)-(-)-pipecolic acid (5) was synthesized in four steps and 47% overall yield starting from 2-cyano-6-phenyloxazolopiperidine (1). A general strategy is described for preparing 2-alkylated and 6-alkylated pipecolic acid 7a-c and 11a-c using diastereoselective procedures.

  DOI：

  10.1021/jo00093a007
• 作为产物：
  描述：

  (3R,5R)-3-(4-iodobutyl)-2-oxo-5-phenyl-morpholine-4-carboxylic acid tert-butyl ester 在 六甲基磷酰三胺 、 双(三甲基硅烷基)氨基钾 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 32.0h， 生成 (4R,9aS)-9a-benzyl-4-phenylhexahydropyrido[2,1-c][1,4]oxazin-1-one
  参考文献：
  名称：

  An efficient, asymmetric synthesis of pipecolic acid and 2-alkyl pipecolic acids

  摘要：

  Both (R)- and (S)-pipecolic acids and their 2-alkyl derivatives have been synthesized via diastereoselective alkylations of (R)-5-phenylmorpholin-2-one 5. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.025

文献信息

• An efficient, asymmetric synthesis of pipecolic acid and 2-alkyl pipecolic acids
  作者：Duen-Ren Hou、Shin-Yi Hung、Chung-Cheng Hu

  DOI：10.1016/j.tetasy.2005.10.025

  日期：2005.11

  Both (R)- and (S)-pipecolic acids and their 2-alkyl derivatives have been synthesized via diastereoselective alkylations of (R)-5-phenylmorpholin-2-one 5. (c) 2005 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis. 32. A New Access to Enantiomerically Pure (S)-(-)-Pipecolic Acid and 2- or 6-Alkylated Derivatives
  作者：J.-F. Berrien、J. Royer、H.-P. Husson

  DOI：10.1021/jo00093a007

  日期：1994.7

  Enantiomerically pure (S)-(-)-pipecolic acid (5) was synthesized in four steps and 47% overall yield starting from 2-cyano-6-phenyloxazolopiperidine (1). A general strategy is described for preparing 2-alkylated and 6-alkylated pipecolic acid 7a-c and 11a-c using diastereoselective procedures.