methyl (S)-1-(4-chlorophenyl)aziridine-2-carboxylate | 4916-17-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (S)-1-(4-chlorophenyl)aziridine-2-carboxylate
• 英文别名: 1-(4-Chlorphenyl)-aziridin-carbonsaeure-2-methylester
• CAS: 4916-17-0
• 化学式: C₁₀H₁₀ClNO₂
• 分子量: 211.648
• InChiKey: LISSBMTZNHZBLL-QHGLUPRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.31
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 (+/-)-1-(4-chlorophenyl)aziridine-2-carbonitrile 在 potassium phosphate buffer 、 Rhodococcus erythropolis AJ₂₇₀ cells 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 methyl (R)-(+)-1-(4-chlorophenyl)aziridine-2-carboxylate 、 S-(-)-1-(4-chlorophenyl)aziridine-2-carboxamide 、 R-1-(4-chlorophenyl)aziridine-2-carboxamide 、 methyl (S)-1-(4-chlorophenyl)aziridine-2-carboxylate
  参考文献：
  名称：

  Nitrile Biotransformations for the Efficient Synthesis of Highly Enantiopure 1-Arylaziridine-2-carboxylic Acid Derivatives and Their Stereoselective Ring-Opening Reactions

  摘要：

  Catalyzed by the Rhodococcus erythropolis AJ270 whole cell catalyst under very mild conditions, biotransformations of racemic 1-arylaziridine-2-carbonitriles proceeded efficiently and enantioselectively to produce highly enantiopure S-1-arylaziridine-2-carboxamides and R-1-arylaziridine-2-carboxylic acids in excellent yields. Although the nitrile hydratase exhibits no selectivity against all nitrile substrates, the amidase is highly R-enantioselective towards 1-arylaziridine-2-carboxamides. When treated with benzyl bromide, 1-phenylaziridine-2S-carboxamide underwent a highly regioselective and enantiospecific ring-opening reaction to afford an almost quantitative yield of R-beta-[(benzyl)phenylamino]-alpha-bromopropanamide (C-2 attack) and R-alpha-[(benzyl)phenylamino]-beta-bromopropanamide (C-3 attack) in a 10.5:1 ratio. Further treatment of the resulting ring-opening products with an N-nucleophilic reagent such as amine and azide led to, through most probably the aziridinium intermediate, the formation of S-alpha-substituted-beta-[(benzyl)phenylamino]propanamides in good chemical yields with high enantiomeric purity.

  DOI：

  10.1021/jo062339v