2-[fluoro(trifluoromethoxy)methyl]-1H-benzimidazole | 224783-43-1

• 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: 2-[fluoro(trifluoromethoxy)methyl]-1H-benzimidazole
• 英文别名: 2-[trifluoromethoxy(fluoro)methyl]benzimidazole；2-(trifluoromethoxyfluoromethyl)benzimidazole
• CAS: 224783-43-1
• 化学式: C₉H₆F₄N₂O
• 分子量: 234.153
• InChiKey: WODXDGLRIWEHDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二茂铁甲醇 、 2-[fluoro(trifluoromethoxy)methyl]-1H-benzimidazole 在 HBF₄ 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到1-ferrocenylmethyl-2-(trifluoromethoxyfluoromethyl)benzimidazole
  参考文献：
  名称：

  Synthesis and structure of biologically active ferrocenylalkyl polyfluoro benzimidazoles

  摘要：

  The title compounds were synthesized in quantitative yields by interacting cl-hydroxyalkyl ferrocenes with polyfluoroalkyl benzimidazoles in an aqueous-organic medium in the presence of HBF4. The resulting diastereomers and enantiomers were resolved using HPLC on silica bonded chiral stationary phases based on chiral cyclodextrins and cyclic antibiotics. The X-ray determination of molecular and crystal structure of 1-ferrocenylmethyl-2-(trifluoromethoxyfluoromethyl)benzimidazole (1) was carried out. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)01097-3
• 作为产物：
  描述：

  三氟甲基三氟乙烯基醚 、 邻苯二胺 以 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到2-[fluoro(trifluoromethoxy)methyl]-1H-benzimidazole
  参考文献：
  名称：

  含氟苯并咪唑衍生物的合成

  摘要：

  通过邻苯二胺、3,4-二氨基甲苯和1,2-二氨基-4-氯苯与六氟丙烯或全氟（甲基乙烯基醚）在DMF中反应得到各种含氟苯并咪唑。开发了一种新的有效合成2-(1,2,2,2-四氟乙基)苯并咪唑的方法，在乙酸乙酯中，在二乙胺或二甲胺存在下，邻苯二胺与六氟丙烯反应。

  DOI：

  10.1007/s11172-010-0060-0

文献信息

• Chekhlov; Martynov, Doklady Chemistry, 1999, vol. 368, # 4-6, p. 249 - 253
  作者：Chekhlov、Martynov

  DOI：——

  日期：——
• Synthesis of fluorine-containing benzimidazole derivatives
  作者：T. P. Vasilyeva、N. M. Karimova、Yu. V. Slavich

  DOI：10.1007/s11172-010-0060-0

  日期：2010.1

  fluorine-containing benzimidazoles were obtained by the reaction of o-phenylene-diamine, 3,4-diaminotoluene, and 1,2-diamino-4-chlorobenzene with hexafluoropropene or perfluoro(methyl vinyl ether) in DMF. A new efficient method of synthesis of 2-(1,2,2,2-tet-rafluoroethyl)benzimidazole by the reaction of o-phenylenediamine with hexafluoropropene in the presence of diethylamine or dimethylamine in ethyl acetate is developed

  通过邻苯二胺、3,4-二氨基甲苯和1,2-二氨基-4-氯苯与六氟丙烯或全氟（甲基乙烯基醚）在DMF中反应得到各种含氟苯并咪唑。开发了一种新的有效合成2-(1,2,2,2-四氟乙基)苯并咪唑的方法，在乙酸乙酯中，在二乙胺或二甲胺存在下，邻苯二胺与六氟丙烯反应。
• Synthesis and structure of biologically active ferrocenylalkyl polyfluoro benzimidazoles
  作者：Lubov’ V. Snegur、Victor I. Boev、Yury S. Nekrasov、Mikhail M. Ilyin、Vadim A. Davankov、Zoya A. Starikova、Alexander I. Yanovsky、Alexey F. Kolomiets、Valery N. Babin

  DOI：10.1016/s0022-328x(98)01097-3

  日期：1999.5

  The title compounds were synthesized in quantitative yields by interacting cl-hydroxyalkyl ferrocenes with polyfluoroalkyl benzimidazoles in an aqueous-organic medium in the presence of HBF4. The resulting diastereomers and enantiomers were resolved using HPLC on silica bonded chiral stationary phases based on chiral cyclodextrins and cyclic antibiotics. The X-ray determination of molecular and crystal structure of 1-ferrocenylmethyl-2-(trifluoromethoxyfluoromethyl)benzimidazole (1) was carried out. (C) 1999 Elsevier Science S.A. All rights reserved.