(3aS,8aR)-3-acryloyl-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one | 172821-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (3aS,8aR)-3-acryloyl-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one
• 英文别名: (3aR,8bS)-1-prop-2-enoyl-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-2-one
• CAS: 172821-12-4
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: ZLJHVZZVSXMZPJ-PWSUYJOCSA-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：
  0.23
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  间戊二烯 、 (3aS,8aR)-3-acryloyl-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one 在 氯化二乙基铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以69%的产率得到(3aR,8bS)-1-[(1R,2S)-2-methylcyclohex-3-ene-1-carbonyl]-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-2-one
  参考文献：
  名称：

  由氨基茚满醇衍生的手性助剂介导的高度非对映选择性狄尔斯-阿尔德反应：构象对非对映选择性的作用

  摘要：

  The oxazolidinone 2 derived from amino indanol 1 functions as a very efficient chiral auxiliary for the Diels-Alder reaction. The effect of conformation has been explored using a range of constrained phenyl glycinol analogues.

  DOI：

  10.1016/0040-4039(95)01584-5
• 作为产物：
  描述：

  (3aS,8aR)-3-((1S,6S)-4,6-Dimethyl-cyclohex-3-enecarbonyl)-3,3a,8,8a-tetrahydro-indeno[1,2-d]oxazol-2-one 在 过氧化氢,锂盐(1:1) 、 三乙胺 、 lithium bromide 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (3aS,8aR)-3-acryloyl-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one
  参考文献：
  名称：

  由氨基茚满醇衍生的手性助剂介导的高度非对映选择性狄尔斯-阿尔德反应：构象对非对映选择性的作用

  摘要：

  The oxazolidinone 2 derived from amino indanol 1 functions as a very efficient chiral auxiliary for the Diels-Alder reaction. The effect of conformation has been explored using a range of constrained phenyl glycinol analogues.

  DOI：

  10.1016/0040-4039(95)01584-5

文献信息

• Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with <i>N</i>-Chloro-<i>N</i>-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts
  作者：Yuta Murakami、Youhei Takeda、Satoshi Minakata

  DOI：10.1021/jo2010632

  日期：2011.8.5

  Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the "matching" stereochemical combination of chiral auxiliary/ammonium salt. For example, when 3-phenyl-(4R,7S)-4-methyl-7-isopropyl-4,S,6,7-tetrahydroindazole (L-menthopyrazole) as a chiral auxiliary and a cinchonidine-derived chiral ammonium salt as a catalyst were applied to the reaction system, perfect diastereoselectivity was realized. Furthermore, the preparation of enantiomerically pure aziridines by removal of the chiral auxiliary was demonstrated.
• Highly diastereoselective diels-alder reaction mediated by a chiral auxiliary derived from amino indanol: The role of conformation on diastereoselectivity
  作者：Ian W. Davies、Chris H. Senanayake、Laurie Castonguay、Robert D. Larsen、Thomas R. Verhoeven、Paul J. Reider

  DOI：10.1016/0040-4039(95)01584-5

  日期：1995.10

  The oxazolidinone 2 derived from amino indanol 1 functions as a very efficient chiral auxiliary for the Diels-Alder reaction. The effect of conformation has been explored using a range of constrained phenyl glycinol analogues.