(3R)-3-phenyltetrahydro-2H-oxazolo[3,2-a]pyridin-5(3H)-one | 835876-41-0

• 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: (3R)-3-phenyltetrahydro-2H-oxazolo[3,2-a]pyridin-5(3H)-one
• 英文别名: (3R)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridin-5-one；(3R)-3-phenyl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS: 835876-41-0
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: QOERGTUYRSMLQN-AMGKYWFPSA-N

物化性质

• 沸点：
  395.1±31.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3R,5R)-3-phenylhexahydro-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile 在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以60%的产率得到(3R)-3-phenyltetrahydro-2H-oxazolo[3,2-a]pyridin-5(3H)-one
  参考文献：
  名称：

  N-(氰甲基)恶唑烷系统的还原和氧化转化以扩大哌啶的手性库

  摘要：

  已利用两种新反应来修饰含有手性、非外消旋 N-（氰甲基）恶唑烷系统的哌啶支架。首先研究了雷尼镍介导的脱氰作用，然后是使用高锰酸钾的氧化过程，以提供对映体纯内酰胺，包括氧代哌啶酸衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400404

文献信息

• Rhodium-catalyzed multicomponent synthesis of chiral oxazolopiperidines
  作者：Jessica Salvadori、Etienne Airiau、Nicolas Girard、André Mann、Maurizio Taddei

  DOI：10.1016/j.tet.2010.03.064

  日期：2010.5

  A multicomponent reaction that employs an unsaturated carboxylic acid, a 1,2 or 1,3 amino alcohol and gaseous CO and H-2 has been discovered. Thus, hydrocarbonylation of the carboxylic acid double bond generates a linear aldehyde, that is, immediately transformed into an oxazolidine. Further microwave assisted intramolecular lactamization delivers oxazolopiperidines with the generation of six new bonds in a one-pot single step. Bicylic, tricyclic, tetracyclic, and spirocyclic oxazolopiperidines can be prepared in good yields and acceptable stereoselection. The reaction did not occur under conventional heating even at higher temperature and pressure and for longer time, showing that microwave heating is indispensable to the process. (C) 2010 Published by Elsevier Ltd.
• CARBAZOLE-CONTAINING AMIDES, CARBAMATES, AND UREAS AS CRYPTOCHROME MODULATORS
  申请人：Synchronicity Pharma, Inc.

  公开号：EP3129366B1

  公开（公告）日：2021-06-09
• Reductive and Oxidative Transformations of the<i>N</i>-(Cyanomethyl)oxazolidine System to Expand the Chiral Pool of Piperidines
  作者：David François、Erwan Poupon、Nicole Kunesch、Henri-Philippe Husson

  DOI：10.1002/ejoc.200400404

  日期：2004.12

  Two new reactions have been exploited to modify piperidine scaffolds containing the chiral, non-racemic N-(cyanomethyl)oxazolidine system. A Raney nickel mediated decyanation was studied first, followed by an oxidative process using potassium permanganate to furnish enantiopure lactams including oxopipecolic acid derivatives. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  已利用两种新反应来修饰含有手性、非外消旋 N-（氰甲基）恶唑烷系统的哌啶支架。首先研究了雷尼镍介导的脱氰作用，然后是使用高锰酸钾的氧化过程，以提供对映体纯内酰胺，包括氧代哌啶酸衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)