N-Formyl-α-amino-crotonsaeure-methylester | 83698-27-5

• 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: N-Formyl-α-amino-crotonsaeure-methylester
• 英文别名: Methyl-2-formylaminocrotonat；Methyl 2-formamidobut-2-enoate；methyl 2-formamidobut-2-enoate
• CAS: 83698-27-5
• 化学式: C₆H₉NO₃
• 分子量: 143.142
• InChiKey: XBWYJYJJWPTJLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Formyl-α-amino-crotonsaeure-methylester 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 生成 methyl 3-bromo-2-(N-formylimino)butanoate
  参考文献：
  名称：

  Characterization of α-halo-imine intermediates derived from halogenation of dehydroamino acid derivatives

  摘要：

  An efficient one-pot Erlenmeyer-Plochl reaction affords high yields of optically active aliphatic dehydroamino acid derivatives. Subsequent halogenation with NBS or NIS yields the alpha-halo-imine derivatives which undergo kinetically controlled tautomerization with Et3N, resulting in increased E selectivity. Isomerization of these derivatives in the presence of strong base (DABCO) results in exclusive formation of the more stable Z vinyl bromides. High yields of the beta-halo-dehydroamino acids are obtained in all cases.

  DOI：

  10.1016/s0040-4039(00)79004-6
• 作为产物：
  描述：

  甲醇 、 甲酸 、 dehydrobutyrine 生成 N-Formyl-α-amino-crotonsaeure-methylester
  参考文献：
  名称：

  Heyns,K.; Gruetzmacher,H.-F., Zeitschrift fur Naturforschung. Teil B. Anorganische Chemie, organische Chemie, Biochemie, Biophysik, Biologie, 1961, vol. 16, p. 293 - 298

  摘要：

  DOI：

文献信息

• Heyns,K.; Gruetzmacher,H.-F., Zeitschrift fur Naturforschung. Teil B. Anorganische Chemie, organische Chemie, Biochemie, Biophysik, Biologie, 1961, vol. 16, p. 293 - 298
  作者：Heyns,K.、Gruetzmacher,H.-F.

  DOI：——

  日期：——
• Characterization of α-halo-imine intermediates derived from halogenation of dehydroamino acid derivatives
  作者：Andrew P. Combs、Robert W. Armstrong

  DOI：10.1016/s0040-4039(00)79004-6

  日期：1992.10

  An efficient one-pot Erlenmeyer-Plochl reaction affords high yields of optically active aliphatic dehydroamino acid derivatives. Subsequent halogenation with NBS or NIS yields the alpha-halo-imine derivatives which undergo kinetically controlled tautomerization with Et3N, resulting in increased E selectivity. Isomerization of these derivatives in the presence of strong base (DABCO) results in exclusive formation of the more stable Z vinyl bromides. High yields of the beta-halo-dehydroamino acids are obtained in all cases.