(S,S,E)-N-(2-Oxocyclohexyl)alanine ethyl ester p-nitrophenylhydrazone | 182699-52-1

• 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: (S,S,E)-N-(2-Oxocyclohexyl)alanine ethyl ester p-nitrophenylhydrazone
• 英文别名: ethyl (2S)-2-[[(1S,2E)-2-[(4-nitrophenyl)hydrazinylidene]cyclohexyl]amino]propanoate
• CAS: 182699-52-1
• 化学式: C₁₇H₂₄N₄O₄
• 分子量: 348.402
• InChiKey: VMJALGHPQNXRNF-SBKSMOTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S,S,E)-N-(2-Oxocyclohexyl)alanine ethyl ester p-nitrophenylhydrazone 在 titanium(III) chloride 作用下， 以 丙酮 为溶剂， 以62%的产率得到(-)-(S)-N-(2-Oxocyclohexyl)alanine ethyl ester
  参考文献：
  名称：

  Reactivity of conjugated azoalkenes towards α-amino acid ethyl esters

  摘要：

  The synthesis of Z- and E-arylhydrazones by 1,4-conjugate addition of glycine, L-alanine and L-tyrosine ethyl esters to phenylazostilbene 1, p-nitrophenylazostilbene 2 and p-nitrophenylazocyclohexene 3 is described. Optically active N-functionalized 2-aminocyclohexanones 22-26 are obtained by TiCl3-catalysed hydrolysis of the corresponding hydrazones. However, they have been shown to be unstable, as they undergo easy oxidation by air. X-Ray analysis of the phenylhydrazone 8a in the Z configuration is also reported.

  DOI：

  10.1039/p19960001961
• 作为产物：
  描述：

  L-丙氨酸乙酯盐酸盐 、 cyclohexen-1-yl-(4-nitrophenyl)diazene 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以44%的产率得到(S,S,E)-N-(2-Oxocyclohexyl)alanine ethyl ester p-nitrophenylhydrazone
  参考文献：
  名称：

  Reactivity of conjugated azoalkenes towards α-amino acid ethyl esters

  摘要：

  The synthesis of Z- and E-arylhydrazones by 1,4-conjugate addition of glycine, L-alanine and L-tyrosine ethyl esters to phenylazostilbene 1, p-nitrophenylazostilbene 2 and p-nitrophenylazocyclohexene 3 is described. Optically active N-functionalized 2-aminocyclohexanones 22-26 are obtained by TiCl3-catalysed hydrolysis of the corresponding hydrazones. However, they have been shown to be unstable, as they undergo easy oxidation by air. X-Ray analysis of the phenylhydrazone 8a in the Z configuration is also reported.

  DOI：

  10.1039/p19960001961

文献信息

• Reactivity of conjugated azoalkenes towards α-amino acid ethyl esters
  作者：Silvano Bozzini、Fulvia Felluga、Giorgio Nardin、Alessandro Pizzioli、Giuliana Pitacco、Ennio Valentin

  DOI：10.1039/p19960001961

  日期：——

  The synthesis of Z- and E-arylhydrazones by 1,4-conjugate addition of glycine, L-alanine and L-tyrosine ethyl esters to phenylazostilbene 1, p-nitrophenylazostilbene 2 and p-nitrophenylazocyclohexene 3 is described. Optically active N-functionalized 2-aminocyclohexanones 22-26 are obtained by TiCl3-catalysed hydrolysis of the corresponding hydrazones. However, they have been shown to be unstable, as they undergo easy oxidation by air. X-Ray analysis of the phenylhydrazone 8a in the Z configuration is also reported.