4,4'-dimethoxyoctafluoroazobenzene | 2010-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4,4'-dimethoxyoctafluoroazobenzene
• 英文别名: 4,4'-dimethoxyperfluoroazobenzene；4,4'-CH3OC6F4NNC6F4-OCH3；4,4'-Dimethoxy-octafluor-azobenzol；Octafluor-4,4'-dimethoxyazobenzol；bis(2,3,5,6-tetrafluoro-4-methoxyphenyl)diazene
• CAS: 2010-67-5
• 化学式: C₁₄H₆F₈N₂O₂
• 分子量: 386.201
• InChiKey: XFUIVKCEOVKWCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4,4'-dimethoxyoctafluoroazobenzene 在 双氧水 、 三氟乙酸酐 作用下， 生成 4,4'-CH3O-C6F4N(O)NC6F4OCH3
  参考文献：
  名称：

  472.芳族多氟化合物。第二十三部分。聚氟偶氮，-氮氧基-和-氢偶氮苯

  摘要：

  DOI：

  10.1039/jr9650002621
• 作为产物：
  描述：

  2,3,4,5,6-五氟苯胺 在 sodium hypochlorite 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 4,4'-dimethoxyoctafluoroazobenzene
  参考文献：
  名称：

  472.芳族多氟化合物。第二十三部分。聚氟偶氮，-氮氧基-和-氢偶氮苯

  摘要：

  DOI：

  10.1039/jr9650002621

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.8, 3, page 55 - 151
  作者：

  DOI：——

  日期：——
• Hydroxyperfluoroazobenzenes: novel inhibitors of enzymes of androgen biosynthesis
  作者：Michael Jarman、S. Elaine Barrie、John J. Deadman、John Houghton、Raymond McCague、Martin G. Rowlands

  DOI：10.1021/jm00171a019

  日期：1990.9

  In a search for inhibitors of 17 alpha-hydroxylase-C17,20-lyase and testosterone-5 alpha-reductase, target enzymes in the development of drugs to treat hormone-dependent prostatic cancer, we have identified certain compounds chemically derived by the hydrolysis of decafluoroazobenzene (4) as novel inhibitors for these two enzymes. Hydrolysis of 4 gave the known 4-hydroxynonafluoroazobenzene (1) and the novel 2-hydroxynonafluoroazobenzene (2). By AlI3 demethylation of 4,4'-dimethoxyoctafluoroazobenzene (5) or by hydrolysis of 4 under phase-transfer conditions 4,4'-dihydroxyoctafluoroazobenzene (3) was obtained. Compounds 1 and 2 were inhibitors of the hydroxylase (IC50 values, respectively, 30 and 63 microM) and of the lyase (IC50 values 33 and 16 microM) steps on the pathway of androgen biosynthesis. The 2-hydroxy compound 2 underwent spontaneous conversion into octafluorodibenz[b,f][1,4,5]oxadiazepine (6) which had IC50 values, respectively, of 50 and 15 microM for the hydroxylase and lyase steps and which contributed to the observed activity of 2. Effective inhibitors of the 5 alpha-reductase were 1 (Ki 10 microM) and 3 (Ki4 microM): the activities of 1 and 3 were markedly pH dependent, with respective IC50 values of 14 and 5 microM at pH 7.4 and of 2 and 0.8 microM at pH 6.6.
• 472. Aromatic polyfluoro-compounds. Part XXIII. Polyfluoroazo, -azoxy-, and -hydrazo-benzenes
  作者：J. Burdon、C. J. Morton、D. F. Thomas

  DOI：10.1039/jr9650002621

  日期：——