(2S,3R,8aS)-3-methyl-2-phenylhexahydro-5H-[1,3]oxazolo[3,2-a]pyridin-5-one | 1115303-09-7

• 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,3R,8aS)-3-methyl-2-phenylhexahydro-5H-[1,3]oxazolo[3,2-a]pyridin-5-one
• 英文别名: (2S,3R,8aS)-3-methyl-2-phenyl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS: 1115303-09-7
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: XRTNQZADCRUCBB-DDTOSNHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  N-[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]but-3-enamide 、 一氧化碳 在 (acetylacetonato)dicarbonylrhodium (l) 、 氢气 、 对甲苯磺酸 、 6,6′-[(3,3′-二叔丁基-5,5′-二甲氧基-1,1′-二苯基-2,2′-二基)双(氧)]双(二苯并[d,f][1,3,2]二噁磷杂庚英) 作用下， 以 四氢呋喃 为溶剂， 70.0 ℃ 、500.01 kPa 条件下， 反应 12.0h， 以78%的产率得到(2S,3R,8aS)-3-methyl-2-phenylhexahydro-5H-[1,3]oxazolo[3,2-a]pyridin-5-one
  参考文献：
  名称：

  通过加氢甲酰化驱动的多米诺序列对氮杂杂环的一般方法。

  摘要：

  描述了易于获得的乙烯基乙酰胺的加氢甲酰化多米诺反应的发展。末端双键的极高区域选择性加氢甲酰基化提供了一个瞬态N-酰基，可以被各种亲核试剂捕获，以非对映选择性的方式产生多个氮杂-杂环骨架。

  DOI：

  10.1002/chem.200801795

文献信息

• Four-Component Reactions toward Fused Heterocyclic Rings
  作者：Etienne Airiau、Nicolas Girard、André Mann、Jessica Salvadori、Maurizio Taddei

  DOI：10.1021/ol902279m

  日期：2009.11.19

  A multicomponent reaction between H-2, CO, an unsaturated carboxylic acid derivative, and binucleophiles has been discovered, This process represents a combination of diversity-oriented synthesis and multicomponent reactions including amidation and hydroformylation, followed by nucleophilic addition to an N-acyliminium ion allowing the generation of six new bonds. Using pi-nucleophiles, the sequence turns into a multicomponent Pictet-Spengler reaction.
• 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.
• A General Approach to Aza-Heterocycles by Means of Domino Sequences Driven by Hydroformylation
  作者：Etienne Airiau、Thomas Spangenberg、Nicolas Girard、Angèle Schoenfelder、Jessica Salvadori、Maurizio Taddei、André Mann

  DOI：10.1002/chem.200801795

  日期：2008.12.8

  The development of hydroformylative domino reactions of easily accessible vinyl acetamides is described. Extremely regioselective hydroformylation of terminal double bounds provides a transient N-acyliminium that can be trapped by various nucleophiles to give several aza-heterocylic scaffolds in a diastereoselective manner.

  描述了易于获得的乙烯基乙酰胺的加氢甲酰化多米诺反应的发展。末端双键的极高区域选择性加氢甲酰基化提供了一个瞬态N-酰基，可以被各种亲核试剂捕获，以非对映选择性的方式产生多个氮杂-杂环骨架。