E-phenyl-2-azo-6-acetyl-morphine | 1019857-06-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: E-phenyl-2-azo-6-acetyl-morphine
• CAS: 1019857-06-7
• 化学式: C₂₅H₂₅N₃O₄
• 分子量: 431.491
• InChiKey: PODITHQICITKQB-UYMVDLBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.72
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  苯胺 、 甲醇(6 -乙酰吗啡) 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.33h， 以42%的产率得到E-phenyl-2-azo-6-acetyl-morphine
  参考文献：
  名称：

  Synthesis and characterization of novel azo-morphine derivatives for possible use in abused drugs analysis

  摘要：

  A new simple and fast spectroscopic method was presented as a new marker for heroin use. Novel azo-morphine derivatives with spectroscopic absorption peaks ranging from 330-470 nm, were synthesized by the coupling of morphine (M) and 6-acetyl morphine (6-AM) with freshly prepared diazonium salt of aniline hydrochloride at 0 degrees C. However, no reaction was observed with codeine under the same reaction conditions. Separation of azo dyes was performed by TLC using tetrahydrofuran and dichloromethane in the ratio 1: 1. The chemical structure of the products was established by their microanalysis, NMR, IR, UV-vis, and mass spectroscopies. Electronic absorption and excitation spectra of the dyes were measured in solvents of different polarities. The dyes exhibited positive solvatochromism, i.e., a bathochromic band shift as the solvent polarity is increased. Also, the fluorescence quantum yield was sensitive to the polarity and the pH of the medium. The UV-vis spectroscopy of spiked compounds in human urine samples was also reported. The drugs (M, 6-AM and mixture of both) were coupled with freshly prepared diazonium salt even at very low concentration of the drugs 10(-9) M. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.034