(4R,7S)-1-acryloyl-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole | 1314042-61-9

• 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-acryloyl-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole
• 英文别名: 1-[(4R,7S)-4-methyl-3-phenyl-7-propan-2-yl-4,5,6,7-tetrahydroindazol-1-yl]prop-2-en-1-one
• CAS: 1314042-61-9
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: ZECGMTWBSQDCLG-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,7S)-1-acryloyl-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole 在 4-二甲氨基吡啶 、 (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 二氯甲烷 为溶剂， 反应 14.0h， 生成 3-苯基-l-薄荷吡唑
  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：

  (-)-薄荷酮 在 盐酸 、 一水合肼 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 甲苯 为溶剂， 反应 20.5h， 生成 (4R,7S)-1-acryloyl-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole 、 2-acryloyl-2-phenyl-l-menthopyrazole
  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

• A practical method for the aziridination of α,β-unsaturated carbonyl compounds with a simple carbamate utilizing sodium hypochlorite pentahydrate
  作者：Takehiro Umeda、Satoshi Minakata

  DOI：10.1039/d1ra04297a

  日期：——

  N-chloro-N-sodio-carbamate by the reaction of simple tert-butyl carbamate with sodium hypochlorite pentahydrate (NaOCl·5H2O) would be a practical and green method for the aziridination of α,β-unsaturated carbonyl compounds. The process described herein is transition-metal free, all of the materials are commercially available, the byproducts (NaCl and H2O) are environmentally benign and the reaction is stereoselective

  简单的氨基甲酸叔丁酯与五水合次氯酸钠(NaOCl·5H 2 O)反应高效生成N-氯代-N-钠-氨基甲酸叔丁酯是一种实用且绿色的α,β氮丙啶化方法-不饱和羰基化合物。本文所述的方法不含过渡金属，所有材料均可商购，副产物（NaCl 和 H 2 O）对环境无害且反应具有立体选择性。所得氮丙啶是氨基酸的潜在前体。