(2R,3R,8aS)-3-(hydroxymethyl)-2-phenylhexahydrooxazolo[3,2-a]pyridin-5-one | 1231260-20-0

• 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: (2R,3R,8aS)-3-(hydroxymethyl)-2-phenylhexahydrooxazolo[3,2-a]pyridin-5-one
• 英文别名: (2R,3R,8aS)-3-(hydroxymethyl)-2-phenyl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS: 1231260-20-0
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: XUVADSPPJWOQAJ-KWCYVHTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙烯基乙酸 、 一氧化碳 、 (1R,2R)-(-)-2-氨基-1-苯基-1,3-丙二醇 在 acetylacetonatodicarbonylrhodium(l) 、 氢气 、 4-甲基苯磺酸吡啶 、 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， 75.0 ℃ 、689.01 kPa 条件下， 反应 1.5h， 以70%的产率得到(2R,3R,8aS)-3-(hydroxymethyl)-2-phenylhexahydrooxazolo[3,2-a]pyridin-5-one
  参考文献：
  名称：

  Rhodium-catalyzed multicomponent synthesis of chiral oxazolopiperidines

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.03.064

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.