1-(4'-methoxyphenyl)-2-(trifluoromethyl)-6-hydroxybenzimidazole | 137927-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(4'-methoxyphenyl)-2-(trifluoromethyl)-6-hydroxybenzimidazole
• 英文别名: 1-(4-methoxyphenyl)-2-trifluoromethyl-6-hydroxybenzimidazol；3-(4-Methoxyphenyl)-2-(trifluoromethyl)benzimidazol-5-ol
• CAS: 137927-35-6
• 化学式: C₁₅H₁₁F₃N₂O₂
• 分子量: 308.26
• InChiKey: UJPTVXMZILZQKA-UHFFFAOYSA-N

物化性质

• 沸点：
  422.1±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,2,2-trifluoro-N-4-methoxyphenyll-N'-4-methoxyphenyl-acetamidine 在 三氟化硼乙醚 sodium perchlorate 作用下， 以 水 、 乙腈 、 苯 为溶剂， 生成 1-(4'-methoxyphenyl)-2-(trifluoromethyl)-6-hydroxybenzimidazole
  参考文献：
  名称：

  Syntheses of 1-aryl-2-trifluoromethylbenzimidazoles via electrochemically prepared p-benzoquinone imines

  摘要：

  Electrooxidation of N-(4-methoxyphenyl)-N'-aryl-2,2,2-trifluoroethanimidamides 1 in an MeCN-H2O-NaClO4-(C)-(Pt) system affords p-benzoquinone imines 2 which are converted to 1-aryl-2-trifluoromethylbenzimidazoles 3 by acid catalyzed cyclization.

  DOI：

  10.1016/s0040-4039(00)79443-3

文献信息

• Thermal electrocyclic spirocyclization of p-benzoquinone imines: A novel synthetic route to trifluoromethylated spirodiazacarbocycles
  作者：Masafumi Kobayashi、Kenji Uneyama、Noritaka Hamada、Setsuo Kashino

  DOI：10.1016/s0040-4039(00)77072-9

  日期：1994.7

  2′-trifluoromethyl-spiro[2,5-cyclohexadiene-1,4′-1H(or 3H)-quinazolin]-4-ones (spirodienone derivatives) (3) and (4), which were transformed to 1,3-diazepine derivative (7) by Lewis acid-catalyzed dienone-phenol rearrangement.

  电化学制备的N-（4-氧代-2,5-环己二烯-1-亚基）-2,2,2,3-三氟乙酰胺（对苯醌衍生物）（2）在DMSO中于120°C加热加热环化成2'-三氟甲基-螺[2,5-环己二烯-1,4'-1 H（或3 H）-喹唑啉] -4-酮（螺二烯酮衍生物）（3）和（4），它们被转化为1,3-二氮杂pine衍生物（7）由路易斯酸催化的二烯酮-苯酚重排。
• Intramolecular Cyclization of N1-(4-Oxo-2,5-cyclohexadien-1-ylidene)-N2-substituted-2,2,2- trifluoroethanimidamides (p-Benzoquinone Imine Derivatives): Syntheses of Trifluoromethylated 6-Hydroxybenzimidazoles and Spiro Dienone Diazacarbocycles
  作者：Masafumi Kobayashi、Kenji Uneyama、Noritaka Hamada、Setsuo Kashino

  DOI：10.1021/jo00125a028

  日期：1995.10

  Lewis acid-catalyzed intramolecular cyclization of N-1-(4-oxo-2,5-cyclohexadien-1-ylidene)-N-2- substituted-2,2,2-trifluoroethanimidamide (p-benzoquinone imine derivatives, 1) prepared by electrooxidation of N-(4-methoxyphenyli-N'-substituted-2,2 2-trifluoroethanimidamides 2 occurred to give 1-substituted-2-(trifluoromethyl)-6-hydroxybenzimidazoles 3. Alternatively, thermal cyclization of 1 gave spiro dienone diazacarbocycles 9 and 10, which were converted into diazepine 12 via a dienone-phenol rearrangement.