(2R,3S)-1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methylaziridine-2-carboxylic acid 1-[methoxy(diphenyl)methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester | 1030379-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methylaziridine-2-carboxylic acid 1-[methoxy(diphenyl)methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
• 英文别名: [(1S,2R,4R)-1-[methoxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2R,3S)-1-(1,3-dioxoisoindol-2-yl)-3-methylaziridine-2-carboxylate
• CAS: 1030379-41-9
• 化学式: C₃₅H₃₆N₂O₅
• 分子量: 564.681
• InChiKey: PIBLPASPEJSENK-MDFODSSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  but-2-enoic acid 1-[methoxy(diphenyl)methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 、 氨基邻苯二甲胺 在 lead(IV) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 (2S,3R)-1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methylaziridine-2-carboxylic acid 1-[methoxy(diphenyl)methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 、 (2R,3S)-1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methylaziridine-2-carboxylic acid 1-[methoxy(diphenyl)methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
  参考文献：
  名称：

  On the scope of diastereoselective aziridination of various chiral auxiliaries derived N- and O-enones with N-aminophthalimide in the presence of lead tetraacetate

  摘要：

  The treatment of a range of N- and O-enones derived from various camphor-based chiral auxiliaries A-D with N-aminoplithalimide in the presence of lead tetraacetate is described. In general, N-phtbalimidoaziridines were obtained with high diastereo-selectivities (up to 98% de) and chemical yields (up to 95%) when 10,10-diphenyl-2,10-camphanediol A derived O-enones with a range of substituents were used under the same reaction conditions. Excellent stereoselectivity was obtained when the N-tosyl camphorpyrazolidinone E derived acrylate was used. The absolute configuration of the new stereogenic center(s) of the major diastereomer was established by X-ray crystallographic analysis. Chiral auxiliary cleavage was achieved under mild reaction conditions. A model to explain the stereochemical induction is also proposed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.028

文献信息

• On the scope of diastereoselective aziridination of various chiral auxiliaries derived N- and O-enones with N-aminophthalimide in the presence of lead tetraacetate
  作者：Pei-Wen Duan、Ching-Chen Chiu、Wei-Der Lee、Li Shiue Pan、Uppala Venkatesham、Zheng-Hao Tzeng、Kwunmin Chen

  DOI：10.1016/j.tetasy.2008.02.028

  日期：2008.4

  The treatment of a range of N- and O-enones derived from various camphor-based chiral auxiliaries A-D with N-aminoplithalimide in the presence of lead tetraacetate is described. In general, N-phtbalimidoaziridines were obtained with high diastereo-selectivities (up to 98% de) and chemical yields (up to 95%) when 10,10-diphenyl-2,10-camphanediol A derived O-enones with a range of substituents were used under the same reaction conditions. Excellent stereoselectivity was obtained when the N-tosyl camphorpyrazolidinone E derived acrylate was used. The absolute configuration of the new stereogenic center(s) of the major diastereomer was established by X-ray crystallographic analysis. Chiral auxiliary cleavage was achieved under mild reaction conditions. A model to explain the stereochemical induction is also proposed. (c) 2008 Elsevier Ltd. All rights reserved.