(Z)-2-((benzyloxy)carbonyl)amino-3-(4-nitrophenyl)-2-propenamide | 1373888-84-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-2-((benzyloxy)carbonyl)amino-3-(4-nitrophenyl)-2-propenamide
• 英文别名: Cbz-p-NO2ΔPhe-NH2
• CAS: 1373888-84-6
• 化学式: C₁₇H₁₅N₃O₅
• 分子量: 341.323
• InChiKey: KQTKXAJKDBUXGB-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  124.56
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-溴丙酮酸乙酯 、 (Z)-2-((benzyloxy)carbonyl)amino-3-(4-nitrophenyl)-2-propenamide 在 碳酸氢钠 、 吡啶 、 三氟乙酸酐 、 ammonium hydroxide 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 14.75h， 以87%的产率得到ethyl (Z)-2-[1-(((benzyloxy)carbonyl)amino)-2-(4-nitrophenyl)vinyl]oxazole-4-carboxylate
  参考文献：
  名称：

  Scope and Limitations of a Modified Hantzsch Reaction for the Synthesis of Oxazole-Dehydroamino Acid Derivatives from Dehydroamino Acid Amides

  摘要：

  A variety of oxazole derivatives that possess an alpha,beta-unsaturated substituent at the 2-position were conveniently synthesized in good yields via a Hantzsch-type reaction between dehydroamino acid amides and P-bromopyruvate derivatives. Furthermore, oxazoles with substituents at the 2- and 5-positions were also obtained in good yields using the corresponding beta-substituted beta-bromopyruvate derivatives. A revised reaction mechanism to explain the enhanced reactivity of dehydroamino acid amides for the Hantzsch-oxazole-type reaction is presented.

  DOI：

  10.3987/com-11-12372
• 作为产物：
  描述：

  (Z)-3-(4-nitrophenyl)-2-(phenylmethoxycarbonylamino)prop-2-enoic acid 在 N,N'-二环己基碳二亚胺 、 N-羟基丁二酰亚胺 、 ammonium hydroxide 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 1.08h， 以82%的产率得到(Z)-2-((benzyloxy)carbonyl)amino-3-(4-nitrophenyl)-2-propenamide
  参考文献：
  名称：

  Scope and Limitations of a Modified Hantzsch Reaction for the Synthesis of Oxazole-Dehydroamino Acid Derivatives from Dehydroamino Acid Amides

  摘要：

  A variety of oxazole derivatives that possess an alpha,beta-unsaturated substituent at the 2-position were conveniently synthesized in good yields via a Hantzsch-type reaction between dehydroamino acid amides and P-bromopyruvate derivatives. Furthermore, oxazoles with substituents at the 2- and 5-positions were also obtained in good yields using the corresponding beta-substituted beta-bromopyruvate derivatives. A revised reaction mechanism to explain the enhanced reactivity of dehydroamino acid amides for the Hantzsch-oxazole-type reaction is presented.

  DOI：

  10.3987/com-11-12372