(3S,8aR)-3-isopropyl-5-oxo-2,3,5,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine | 122383-36-2

• 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: (3S,8aR)-3-isopropyl-5-oxo-2,3,5,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine
• 英文别名: (3S,8aR)-3-isopropylhexahydro-5H-[1,3]oxazolo[3,2-a]pyridin-5-one；(3S,8aR)-3-isopropyl-5-oxo-2,3,5,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine；(3S,8aR)-3-propan-2-yl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS: 122383-36-2
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: QYLYUDHBNLPRQW-PSASIEDQSA-N

物化性质

• 沸点：
  303.1±21.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,8aR)-3-isopropyl-5-oxo-2,3,5,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以76%的产率得到
  参考文献：
  名称：

  手性前体，用于合成对映体纯的哌啶。（R）-（-）-丝氨酸的全合成

  摘要：

  手性的制备顺式-和反式-oxazolopiperidones 1，2，和3通过替代程序和哌啶生物碱的有效合成（- [R ）- （ - ） -从毒芹碱反式- 1报道。

  DOI：

  10.1016/s0040-4039(00)76803-1
• 作为产物：
  描述：

  5-氧代戊酸甲酯 在 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (3S,8aR)-3-isopropyl-5-oxo-2,3,5,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine
  参考文献：
  名称：

  手性前体，用于合成对映体纯的哌啶。（R）-（-）-丝氨酸的全合成

  摘要：

  手性的制备顺式-和反式-oxazolopiperidones 1，2，和3通过替代程序和哌啶生物碱的有效合成（- [R ）- （ - ） -从毒芹碱反式- 1报道。

  DOI：

  10.1016/s0040-4039(00)76803-1

文献信息

• 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。
• Improvement of the Synthesis of Chiral Non-Racemic Bicyclic Lactams in the Piperidin-2-ones Series
  作者：Laurent Micouin、Jean-Charles Quirion、Henri-Philippe Husson

  DOI：10.1080/00397919608003529

  日期：1996.4

  Abstract Bicyclic lactams 8 have been prepared in enantiomerically pure form from the corresponding amino esters 5 and glutaric anhydride. The key step is the reduction of imides 7 in methanol. Selective reduction of 8 furnished N-substituted lactams 9.

  摘要 双环内酰胺 8 已从相应的氨基酯 5 和戊二酸酐以对映体纯形式制备。关键步骤是在甲醇中还原酰亚胺 7。选择性还原 8 种提供的 N-取代内酰胺 9.
• 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.
• A facile synthesis of chiral bicyclic lactams utilized in the formation of chiral quaternary carbon compounds
  作者：A. I. Meyers、Bruce A. Lefker、Thomas J. Sowin、Larry J. Westrum

  DOI：10.1021/jo00278a053

  日期：1989.8
• 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.