C^α-methyl-D,L-cinnamylglycinamide | 144095-20-5

• 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: C^α-methyl-D,L-cinnamylglycinamide
• 英文别名: 2-amino-2-methyl-5-phenylpent-4-enamide
• CAS: 144095-20-5
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: AAYJFJQAAMNQBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  C^α-methyl-D,L-cinnamylglycinamide 生成 C^α-methyl-L-cinnamylglycine
  参考文献：
  名称：

  Enzymatic resolution of α,α-disubstituted α-amino acid esters and amides

  摘要：

  The scope and limitations of the enzymatic resolution of alpha,alpha-disubstituted alpha-amino acid amides by an amino acid amidase from Mycobacterium neoaurum and of the corresponding ethyl esters with Pig liver esterase (PLE) have been studied. Moderate enantiomeric excesses were obtained with PLE, with only a narrow substrate specificity. Mycobacterium neoaurum on the contrary yields a broad range of S-alpha,alpha-disubstituted alpha-amino acids 1 and the corresponding R-amides 2.

  DOI：

  10.1016/s0957-4166(00)80217-7
• 作为产物：
  描述：

  (Z)-2-Methyl-5-phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-pent-4-enoic acid amide 在 盐酸 、 水 作用下， 生成 C^α-methyl-D,L-cinnamylglycinamide
  参考文献：
  名称：

  Enantiopure Cα-tetrasubstituted α-amino acids. Chemo-enzymatic synthesis and application to turn-forming peptides

  摘要：

  By a chemo-enzymatic approach we carried out a large-scale synthesis of four enantiopure, sterically constrained, C-alpha-tetra-substituted alpha -amino acids, all characterized by a sidechain (CCdelta)-C-gamma double bond. By using one of them (L-Mag), we prepared an N-alpha-protected tetrapeptide benzylamide which was shown to adopt a beta -turn conformation and to efficiently undergo ring-closing olefin metathesis. (C) 2001 Elsevier Science Led. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00548-8