methyl (S)-(-)-3-(benzylamino)-4-carbamoylbutanoate | 496881-80-2

• 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)-(-)-3-(benzylamino)-4-carbamoylbutanoate
• 英文别名: methyl (3S)-5-amino-3-(benzylamino)-5-oxopentanoate
• CAS: 496881-80-2
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: CCECXVZBMISRGB-NSHDSACASA-N

物化性质

• 沸点：
  461.5±45.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (S)-(-)-3-(benzylamino)-4-carbamoylbutanoate 在 碘苯二乙酸 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 dimethyl (3R,3'R)-(+)-3,3'-bis[(N-benzyl-N-benzyloxycarbonyl)amino]-4,4'-ureylenedibutanoate
  参考文献：
  名称：

  Synthesis of (R)-3,4-Diaminobutanoic Acid by Desymmetrization of Dimethyl 3-(Benzylamino)glutarate through Enzymatic Ammonolysis

  摘要：

  Lipase B from Candida antarctica is shown to be a highly efficient catalyst for the desymmetrization of dimethyl 3-(benzylamino)glutarate (1) through aminolysis and ammonolysis reactions. Using this procedure, enantiopure monoamides are obtained in high yield. The synthetic value of these compounds is demonstrated by the preparation of an enantiopure nonnatural amino acid, i.e. (R)-3,4-diaminobutanoic acid [(+)-12].

  DOI：

  10.1021/jo026254f
• 作为产物：
  描述：

  戊烯二酸二甲酯 在 Candida antarctica lipase B 、 氨 作用下， 以 1,4-二氧六环 为溶剂， 反应 144.0h， 生成 methyl (S)-(-)-3-(benzylamino)-4-carbamoylbutanoate
  参考文献：
  名称：

  Synthesis of (R)-3,4-Diaminobutanoic Acid by Desymmetrization of Dimethyl 3-(Benzylamino)glutarate through Enzymatic Ammonolysis

  摘要：

  Lipase B from Candida antarctica is shown to be a highly efficient catalyst for the desymmetrization of dimethyl 3-(benzylamino)glutarate (1) through aminolysis and ammonolysis reactions. Using this procedure, enantiopure monoamides are obtained in high yield. The synthetic value of these compounds is demonstrated by the preparation of an enantiopure nonnatural amino acid, i.e. (R)-3,4-diaminobutanoic acid [(+)-12].

  DOI：

  10.1021/jo026254f

文献信息

• Synthesis of (<i>R</i>)-3,4-Diaminobutanoic Acid by Desymmetrization of Dimethyl 3-(Benzylamino)glutarate through Enzymatic Ammonolysis
  作者：Mónica López-García、Igancio Alfonso、Vicente Gotor

  DOI：10.1021/jo026254f

  日期：2003.1.1

  Lipase B from Candida antarctica is shown to be a highly efficient catalyst for the desymmetrization of dimethyl 3-(benzylamino)glutarate (1) through aminolysis and ammonolysis reactions. Using this procedure, enantiopure monoamides are obtained in high yield. The synthetic value of these compounds is demonstrated by the preparation of an enantiopure nonnatural amino acid, i.e. (R)-3,4-diaminobutanoic acid [(+)-12].