N-<(2,2,2-Trichloroethoxy)carbonyl>-(S)-α-(2-propenyl)-α-alanine | 160281-15-2

• 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: N-<(2,2,2-Trichloroethoxy)carbonyl>-(S)-α-(2-propenyl)-α-alanine
• 英文别名: (2S)-2-methyl-2-(2,2,2-trichloroethoxycarbonylamino)pent-4-enoic acid
• CAS: 160281-15-2
• 化学式: C₉H₁₂Cl₃NO₄
• 分子量: 304.558
• InChiKey: YTPIRLJYCPLNHN-QMMMGPOBSA-N

物化性质

• 沸点：
  408.1±45.0 °C(predicted)
• 密度：
  1.427±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(2,2,2-Trichloroethoxy)carbonyl>-(S)-α-(2-propenyl)-α-alanine 在 四氯化锡 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 N--α-alanyl>-(R)-alanine methyl ester
  参考文献：
  名称：

  Synthesis of Modified Partial Structures of the Bacterial Cell Wall. 2. Retarded Metabolism of Lipopeptides by Insertion of .alpha.-Substituted .alpha.-Amino Acids

  摘要：

  The synthesis of the lipopeptide 1, which exhibits both immunological activity (induction of the colony stimulating factor (CSF)) and stability against metabolic degradation, has been described. A detailed investigation of the course of the ene reaction between the dipeptide 21 and butyl glyoxylate enabled us to use this type of pericyclic reaction for the establishment of the essential pentenoic acid side chain in 23. The required amino acid 15 was obtained by enzymatic hydrolysis of the corresponding rac-ester 19. The absolute configuration of 1 was assigned by oxidative cleavage of the double bond in 24 and 25 followed by comparison of the degradation products with authentic samples.

  DOI：

  10.1021/jo00094a038
• 作为产物：
  描述：

  (S)-(-)-α-烯丙基丙氨酸 、 氯甲酸-2,2,2-三氯乙酯 在 sodium hydroxide 作用下， 以58%的产率得到N-<(2,2,2-Trichloroethoxy)carbonyl>-(S)-α-(2-propenyl)-α-alanine
  参考文献：
  名称：

  Synthesis of Modified Partial Structures of the Bacterial Cell Wall. 2. Retarded Metabolism of Lipopeptides by Insertion of .alpha.-Substituted .alpha.-Amino Acids

  摘要：

  The synthesis of the lipopeptide 1, which exhibits both immunological activity (induction of the colony stimulating factor (CSF)) and stability against metabolic degradation, has been described. A detailed investigation of the course of the ene reaction between the dipeptide 21 and butyl glyoxylate enabled us to use this type of pericyclic reaction for the establishment of the essential pentenoic acid side chain in 23. The required amino acid 15 was obtained by enzymatic hydrolysis of the corresponding rac-ester 19. The absolute configuration of 1 was assigned by oxidative cleavage of the double bond in 24 and 25 followed by comparison of the degradation products with authentic samples.

  DOI：

  10.1021/jo00094a038

文献信息

• Synthesis of Modified Partial Structures of the Bacterial Cell Wall. 2. Retarded Metabolism of Lipopeptides by Insertion of .alpha.-Substituted .alpha.-Amino Acids
  作者：Alexandra Frauer、Michaela Mehlfuehrer、Klaus Thirring、Heinz Berner

  DOI：10.1021/jo00094a038

  日期：1994.7

  The synthesis of the lipopeptide 1, which exhibits both immunological activity (induction of the colony stimulating factor (CSF)) and stability against metabolic degradation, has been described. A detailed investigation of the course of the ene reaction between the dipeptide 21 and butyl glyoxylate enabled us to use this type of pericyclic reaction for the establishment of the essential pentenoic acid side chain in 23. The required amino acid 15 was obtained by enzymatic hydrolysis of the corresponding rac-ester 19. The absolute configuration of 1 was assigned by oxidative cleavage of the double bond in 24 and 25 followed by comparison of the degradation products with authentic samples.