(4R,7S)-1-[{(2'S)-(1'-benzyloxycarbonyl)aziridin-2'-yl}carbonyl]-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole | 1314042-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4R,7S)-1-[{(2'S)-(1'-benzyloxycarbonyl)aziridin-2'-yl}carbonyl]-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole
• 英文别名: benzyl (2S)-2-[(4R,7S)-4-methyl-3-phenyl-7-propan-2-yl-4,5,6,7-tetrahydroindazole-1-carbonyl]aziridine-1-carboxylate
• CAS: 1314042-77-7
• 化学式: C₂₈H₃₁N₃O₃
• 分子量: 457.572
• InChiKey: DICKVSOKVVLPKR-CETINUKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (4R,7S)-1-[{(2'S)-(1'-benzyloxycarbonyl)aziridin-2'-yl}carbonyl]-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole 在 4-二甲氨基吡啶 作用下， 反应 5.0h， 以78%的产率得到(S)-(-)-N-Z-吖丙啶-2-羧酸甲酯
  参考文献：
  名称：

  Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with N-Chloro-N-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts

  摘要：

  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.

  DOI：

  10.1021/jo2010632
• 作为产物：
  描述：

  (3R,6S)-2-Benzoyl-3-methyl-6-isopropylcyclohexanone 在 盐酸 、 一水合肼 、 三乙胺 、 (2S,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-2-[(R)-(prop-2-en-1-yloxy)(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium bromide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 54.0h， 生成 (4R,7S)-1-[{(2'S)-(1'-benzyloxycarbonyl)aziridin-2'-yl}carbonyl]-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole
  参考文献：
  名称：

  Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with N-Chloro-N-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts

  摘要：

  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.

  DOI：

  10.1021/jo2010632

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.