(3R,5S,8aR)-3-Phenylhexahydrooxazolo<3,2-a>pyridine-5-carboxylic acid amide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,5S,8aR)-3-Phenylhexahydrooxazolo<3,2-a>pyridine-5-carboxylic acid amide
• 英文别名: (3R,5S,8aR)-3-phenyl-3,5,6,7,8,8a-hexahydro-2H-[1,3]oxazolo[3,2-a]pyridine-5-carboxamide
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: AXBBQAMZWDPWSY-RWMBFGLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (-)-2-氰-6-苯基恶唑哌啶 在 potassium carbonate 双氧水 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 生成 (3R,5S,8aS)-3-Phenylhexahydrooxazolo<3,2-a>pyridine-5-carboxylic acid amide 、 (3R,5S,8aR)-3-Phenylhexahydrooxazolo<3,2-a>pyridine-5-carboxylic acid amide
  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

文献信息

• 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.