(S)-methyl 4-azido-4-phenylbutanoate | 1387516-97-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-methyl 4-azido-4-phenylbutanoate
• 英文别名: methyl (4S)-4-azido-4-phenylbutanoate
• CAS: 1387516-97-3
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: NNXBDMRQCVKVGT-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-methyl 4-azido-4-phenylbutanoate 在 palladium 10% on activated carbon 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 5-phenylpyrrolidin-2-one
  参考文献：
  名称：

  Tandem Ring-Opening Decarboxylation of Cyclopropane Hemimalonates with Sodium Azide: A Short Route to γ-Aminobutyric Acid Esters

  摘要：

  Cyclopropane hemimalonates, when treated with sodium azide, undergo a tandem ring-opening decarboxylation to produce gamma-azidobutyric acids in good yields. These adducts were hydrogenated to form gamma-aminobutyric acid (GABA) methyl esters.

  DOI：

  10.1021/jo3010606
• 作为产物：
  描述：

  (2S)-1-(methoxycarbonyl)-2-phenylcyclopropanecarboxylic acid 在 sodium azide 、 氯化铵 作用下， 以 甲乙醚 、 水 为溶剂， 反应 2.0h， 以78%的产率得到(S)-methyl 4-azido-4-phenylbutanoate
  参考文献：
  名称：

  Tandem Ring-Opening Decarboxylation of Cyclopropane Hemimalonates with Sodium Azide: A Short Route to γ-Aminobutyric Acid Esters

  摘要：

  Cyclopropane hemimalonates, when treated with sodium azide, undergo a tandem ring-opening decarboxylation to produce gamma-azidobutyric acids in good yields. These adducts were hydrogenated to form gamma-aminobutyric acid (GABA) methyl esters.

  DOI：

  10.1021/jo3010606

文献信息

• Tandem Ring-Opening Decarboxylation of Cyclopropane Hemimalonates with Sodium Azide: A Short Route to γ-Aminobutyric Acid Esters
  作者：Michael R. Emmett、Huck K. Grover、Michael A. Kerr

  DOI：10.1021/jo3010606

  日期：2012.8.3

  Cyclopropane hemimalonates, when treated with sodium azide, undergo a tandem ring-opening decarboxylation to produce gamma-azidobutyric acids in good yields. These adducts were hydrogenated to form gamma-aminobutyric acid (GABA) methyl esters.