(-)-(S,S,E)-N-(2-Oxo-1,2-diphenylethyl)tyrosine ethyl ester p-nitrophenylhydrazone

• 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-Oxo-1,2-diphenylethyl)tyrosine ethyl ester p-nitrophenylhydrazone
• 英文别名: ethyl (2S)-3-(4-hydroxyphenyl)-2-[[(1S,2E)-2-[(4-nitrophenyl)hydrazinylidene]-1,2-diphenylethyl]amino]propanoate
• 化学式: C₃₁H₃₀N₄O₅
• 分子量: 538.603
• InChiKey: CIKZNMVLKRSYCL-RLQCFBBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙醯苯偶姻 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 (-)-(S,S,E)-N-(2-Oxo-1,2-diphenylethyl)tyrosine 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.