(E)-4-amino-2-methylbut-2-enoic acid | 69169-58-0

• 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: (E)-4-amino-2-methylbut-2-enoic acid
• 英文别名: trans-2-methylcrotonic acid；(E)-4-Amino-2-methylbut-2-ensaeure；2-MeTACA
• CAS: 69169-58-0
• 化学式: C₅H₉NO₂
• 分子量: 115.132
• InChiKey: TVVRNFOZHWBSAV-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  惕各酸乙酯 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 54.0h， 生成 (E)-4-amino-2-methylbut-2-enoic acid
  参考文献：
  名称：

  Synthesis and resolution of 2-methyl analogues of GABA

  摘要：

  E-4-Amino-2-methylbut-2-enoic acid, (+/-)-4-amino-2-methylbutanoic acid, (+)-(S)- and (-)-(R)-4-amino-2-methylbutanoic acid, which are analogues of the inhibitory neurotransmitter GABA (gamma-aminobutyric acid, 4-aminobutanoic acid), were synthesised from ethyl 2-methyl-4-phthalimidobut-2-enoate, ethyl 2-methyl-4-phthilimidobutanoate, (+)+2R-(3,3-dimethylbutyro-1,4-lactonyl)]-(2S)-methyl-4-phthalimidobutanoate and (-)-[(2R-(3,3-dimethylbutyro-1,4-lactonyl)]-(2R)-methyl-4-phthalimidobutanoate, respectively. The assignment of the absolute configuration of (+)-(S)- and (-)-(R)-4-amino-2-methylbutanoic acid was based on the X-ray crystallographic structure of the (+)-(R,S)-diastereoisomer, and direct comparison of specific rotations with the published data for (-)-(R)-4-amino-2-methylbutanoic acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.002

文献信息

• Allan,R.D.; Twitchin,B., Australian Journal of Chemistry, 1978, vol. 31, p. 2283 - 2289
  作者：Allan,R.D.、Twitchin,B.

  DOI：——

  日期：——
• Synthesis and resolution of 2-methyl analogues of GABA
  作者：Rujee K. Duke、Mary Chebib、David E. Hibbs、Kenneth N. Mewett、Graham A.R. Johnston

  DOI：10.1016/j.tetasy.2004.04.002

  日期：2004.6

  E-4-Amino-2-methylbut-2-enoic acid, (+/-)-4-amino-2-methylbutanoic acid, (+)-(S)- and (-)-(R)-4-amino-2-methylbutanoic acid, which are analogues of the inhibitory neurotransmitter GABA (gamma-aminobutyric acid, 4-aminobutanoic acid), were synthesised from ethyl 2-methyl-4-phthalimidobut-2-enoate, ethyl 2-methyl-4-phthilimidobutanoate, (+)+2R-(3,3-dimethylbutyro-1,4-lactonyl)]-(2S)-methyl-4-phthalimidobutanoate and (-)-[(2R-(3,3-dimethylbutyro-1,4-lactonyl)]-(2R)-methyl-4-phthalimidobutanoate, respectively. The assignment of the absolute configuration of (+)-(S)- and (-)-(R)-4-amino-2-methylbutanoic acid was based on the X-ray crystallographic structure of the (+)-(R,S)-diastereoisomer, and direct comparison of specific rotations with the published data for (-)-(R)-4-amino-2-methylbutanoic acid. (C) 2004 Elsevier Ltd. All rights reserved.