(4aS,5aS,10bR)-2,3,4,4a,6,10b-hexahydro-1H,5aH-indeno[1',2':4,5][1,3]oxazolo[3,2-a]pyridin-1-one | 1196714-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (4aS,5aS,10bR)-2,3,4,4a,6,10b-hexahydro-1H,5aH-indeno[1',2':4,5][1,3]oxazolo[3,2-a]pyridin-1-one
• 英文别名: (1R,7S,9S)-8-oxa-2-azatetracyclo[7.7.0.02,7.011,16]hexadeca-11,13,15-trien-3-one
• CAS: 1196714-45-0
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: JUGUQEVYHHFRCF-FPMFFAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• 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：

  聚合甲醛 、 N-[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]but-3-enamide 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 2,2'-双(二苯基磷)联苯 作用下， 以 水 、 甲苯 为溶剂， 反应 0.5h， 以80%的产率得到(4aS,5aS,10bR)-2,3,4,4a,6,10b-hexahydro-1H,5aH-indeno[1',2':4,5][1,3]oxazolo[3,2-a]pyridin-1-one
  参考文献：
  名称：

  Microwave-Assisted Domino Hydroformylation without Syngas

  摘要：

  氢甲酰化是一种强大的反应，但一直因使用气态H2和CO而饱受一些负面偏见。现在，在微波辐射下，只需几分钟，就可以使用水合甲醛作为H2和CO的替代品，在复杂的底物上进行氢甲酰化和不同的环羟基化反应。森本开发的催化系统（用于分解甲醛的Rh/BINAP和用于氢甲酰化的Rh/Xantphos）与微波介电加热和含有配体原子的复杂底物兼容，无需使用外部气态H2和CO（气瓶）供应，也无需任何特殊的安全限制或装置，即可快速进行多米诺氢甲酰化环化反应。

  DOI：

  10.1055/s-0030-1259281

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.
• Microwave-Assisted Domino Hydroformylation without Syngas
  作者：Maurizio Taddei、Elena Cini、Etienne Airiau、Nicolas Girard、André Mann、Jessica Salvadori

  DOI：10.1055/s-0030-1259281

  日期：2011.1

  Hydroformylation is a powerful reaction that has suffered for some negative prejudices related to the use of gaseous H2 and CO. Now it is possible to carry out hydroformylation and different cyclohydrocarbonylations, even on complex substrates, using aqueous formalin as H2 and CO surrogate in few minutes under microwave irradiation. The catalytic system developed by Morimoto (Rh/BINAP for decomposition of formaldehyde and Rh/Xantphos for hydroformylation) is compatible with microwave dielectric heating and with complex substrates containing ligand atoms allowing rapid domino hydroformylation cyclization reactions without using the external supply of gaseous H2 and CO (gas cylinder) and without any particular safety limitation or device.

  氢甲酰化是一种强大的反应，但一直因使用气态H2和CO而饱受一些负面偏见。现在，在微波辐射下，只需几分钟，就可以使用水合甲醛作为H2和CO的替代品，在复杂的底物上进行氢甲酰化和不同的环羟基化反应。森本开发的催化系统（用于分解甲醛的Rh/BINAP和用于氢甲酰化的Rh/Xantphos）与微波介电加热和含有配体原子的复杂底物兼容，无需使用外部气态H2和CO（气瓶）供应，也无需任何特殊的安全限制或装置，即可快速进行多米诺氢甲酰化环化反应。