(2R,3S)-(-)-1-methyl-3-phenylaziridine-2-carboxamide | 960290-87-3

• 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: (2R,3S)-(-)-1-methyl-3-phenylaziridine-2-carboxamide
• 英文别名: (2R,3S)-1-methyl-3-phenylaziridine-2-carboxamide
• CAS: 960290-87-3
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: GQCPWWWXTOIVBD-JIMHFIIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-(-)-1-methyl-3-phenylaziridine-2-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以96%的产率得到(R)-(-)-α-methylamino-β-phenylpropionamide
  参考文献：
  名称：

  Nitrile and Amide Biotransformations for the Synthesis of Enantiomerically Pure 3-Arylaziridine-2-carboxamide Derivatives and Their Stereospecific Ring-Opening Reactions

  摘要：

  [Graphics]Catalyzed by Rhodococcus erythropolis AJ270 (whole cell catalyst) under very mild conditions, a number of racemic trans-3-arylaziridine-2-carbonitriles and amides were efficiently transformed into enantiopure 2R,3S-3-arylaziridine2-carboxamides. While the nitrile hydratase exhibits low selectivity against nitrile substrates, the amidase is highly enantioselective toward 2S,3R-3-arylaziridine-2-carboxamides. Upon the treatment with catalytic hydrogenation, amine, or water in the presence of one equivalent of TFA, the resulting aziridine-2-carboxamides underwent highly efficient and stereospecific ring-opening reactions to produce enantiopure (alpha-amino-, alpha,beta-diamino-, and (alpha-amino-beta-hydroxypropanamide derivatives in high yields.

  DOI：

  10.1021/jo701732h
• 作为产物：
  描述：

  trans-(+/-)-1-methyl-3-phenylaziridine-2-carbonitrile 在 Rhodococcus erythropolis AJ₂₇₀ 作用下， 以 phosphate buffer 为溶剂， 反应 0.7h， 以48%的产率得到(2R,3S)-(-)-1-methyl-3-phenylaziridine-2-carboxamide
  参考文献：
  名称：

  Nitrile and Amide Biotransformations for the Synthesis of Enantiomerically Pure 3-Arylaziridine-2-carboxamide Derivatives and Their Stereospecific Ring-Opening Reactions

  摘要：

  [Graphics]Catalyzed by Rhodococcus erythropolis AJ270 (whole cell catalyst) under very mild conditions, a number of racemic trans-3-arylaziridine-2-carbonitriles and amides were efficiently transformed into enantiopure 2R,3S-3-arylaziridine2-carboxamides. While the nitrile hydratase exhibits low selectivity against nitrile substrates, the amidase is highly enantioselective toward 2S,3R-3-arylaziridine-2-carboxamides. Upon the treatment with catalytic hydrogenation, amine, or water in the presence of one equivalent of TFA, the resulting aziridine-2-carboxamides underwent highly efficient and stereospecific ring-opening reactions to produce enantiopure (alpha-amino-, alpha,beta-diamino-, and (alpha-amino-beta-hydroxypropanamide derivatives in high yields.

  DOI：

  10.1021/jo701732h

文献信息

• Nitrile and Amide Biotransformations for the Synthesis of Enantiomerically Pure 3-Arylaziridine-2-carboxamide Derivatives and Their Stereospecific Ring-Opening Reactions
  作者：Jin-Yuan Wang、De-Xian Wang、Jie Pan、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo701732h

  日期：2007.11.1

  [Graphics]Catalyzed by Rhodococcus erythropolis AJ270 (whole cell catalyst) under very mild conditions, a number of racemic trans-3-arylaziridine-2-carbonitriles and amides were efficiently transformed into enantiopure 2R,3S-3-arylaziridine2-carboxamides. While the nitrile hydratase exhibits low selectivity against nitrile substrates, the amidase is highly enantioselective toward 2S,3R-3-arylaziridine-2-carboxamides. Upon the treatment with catalytic hydrogenation, amine, or water in the presence of one equivalent of TFA, the resulting aziridine-2-carboxamides underwent highly efficient and stereospecific ring-opening reactions to produce enantiopure (alpha-amino-, alpha,beta-diamino-, and (alpha-amino-beta-hydroxypropanamide derivatives in high yields.