5-fluoro-2-propyl-1H-benzimidazole | 1104075-66-2

• 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: 5-fluoro-2-propyl-1H-benzimidazole
• 英文别名: 5-fluoro-2-propylbenzimidazole；6-fluoro-2-propyl-1H-benzimidazole
• CAS: 1104075-66-2
• 化学式: C₁₀H₁₁FN₂
• 分子量: 178.209
• InChiKey: MOBZCYBRQMHBNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三正丁胺 、 4-氟-1,2-苯二胺 在 2-丁烯腈 、 palladium 10% on activated carbon 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以81%的产率得到5-fluoro-2-propyl-1H-benzimidazole
  参考文献：
  名称：

  多相Pd催化氧化CH活化叔胺微波辅助合成多取代苯并咪唑

  摘要：

  可以使用叔胺代替醛和羧酸衍生物作为合成苯并咪唑的伙伴。开发了多相催化下的脱氢胺活化，用于将叔胺直接转化为苯并咪唑。良好的收率和催化剂的有效回收和再循环是这种新方法的一些优点，这表明使用简单的烯烃作为整体氧化剂。通过使用聚焦微波加热观察到反应速率提高。

  DOI：

  10.1002/ejoc.201101001

文献信息

• Rhodium catalyzed 2‐alkyl‐benzimidazoles synthesis from benzene‐1,2‐diamines and tertiary alkylamines as alkylating agents
  作者：Yamini、Saurabh Sharma、Pralay Das

  DOI：10.1002/aoc.6278

  日期：2021.8

  synthesized from benzene-1,2-diamine and tertiary amines as alkylating agent under polystyrene supported rhodium (Rh@PS) nanoparticles (NPs) catalyzed conditions. The heterogeneous rhodium catalyst was applied first time for the synthesis of 2-alkyl-benzimidazoles. The reaction followed through oxidation of alkylamines, transamination, and oxidative cyclisation with benzene-1,2-diamines for the corresponding

  在聚苯乙烯负载的铑（Rh@PS）纳米颗粒（NPS）催化条件下，以苯-1,2-二胺和叔胺为烷基化剂合成了取代的2-烷基-苯并咪唑。多相铑催化剂首次用于合成2-烷基-苯并咪唑。该反应通过烷基胺的氧化、氨基转移和与苯-1,2-二胺的氧化环化以良好的产率合成相应的产物。该工艺适用于广泛的底物范围，可以容忍多个官能团，并且 Rh@PS 催化剂最多可循环使用 4 次，催化活性没有显着损失。
• Ag–TiO₂/Clay Composite Photocatalyst for the Oxidation–Cyclization of 1,2-Diamine Compounds with Propylene Glycol or Alcohols
  作者：Kaliyamoorthy Selvam、Mari Annadhasan、Rengasamy Velmurugan、Meenakshisundaram Swaminathan

  DOI：10.1246/bcsj.20090319

  日期：2010.7.15

  Silver-loaded TiO2 (Ag–TiO2) and acidic clay (K10 montmorillonite) composite photocatalyst has been successfully applied for the light-induced conversion of o-phenylenediamine (OPD) and its derivatives to substituted benzimidazoles with various alcohols in acetonitrile using UV-A and solar light. The influence of the various photocatalysts, solvents, and substituents on the yield and selectivity of the products has been investigated. The mechanism of photocatalysis is proposed. Loading silver on TiO2 enhances product yield and selectivity both in UV and solar light. In the presence of primary alcohols, 2-aminothiophenol forms only disulfide and hence Ag–TiO2/clay can be used as a green catalyst for the synthesis of disulfides.

  负载银的TiO2（Ag–TiO2）和酸性粘土（K10蒙脱石）复合光催化剂已成功应用于紫外A和太阳光诱导的邻苯二胺（OPD）及其衍生物与多种醇在乙腈中的光催化转化合成取代苯并咪唑。考察了不同光催化剂、溶剂和取代基对产物收率和选择性的影响。提出了光催化机理。在TiO2上负载银可以提高紫外和太阳光下产物的收率和选择性。在存在一级醇的情况下，2-氨基硫酚仅形成二硫化物，因此Ag–TiO2/粘土可用作合成二硫化物的绿色催化剂。
• Synthesis of α-Chloroaldoxime <i>O</i>-Methanesulfonates and Their Use in the Synthesis of Functionalized Benzimidazoles
  作者：Yuhei Yamamoto、Hiroo Mizuno、Takayuki Tsuritani、Toshiaki Mase

  DOI：10.1021/jo8023544

  日期：2009.2.6

  Three different alpha-chloroaldoxime O-methanesulfonates were synthesized to investigate their chemical properties. The compounds were found to be stable and were able to be stored at ambient temperature without any precautions. The reactions with anilines were investigated, and it was found that an additive is required to activate the sulfonate. TMEDA was found to be the most efficient additive, and various benzimidazoles were synthesized through the reaction.
• BENZIMIDAZOLE DERIVATIVES AND METHODS OF USE THEREOF
  申请人：Aslanian Robert G.

  公开号：US20100144591A1

  公开（公告）日：2010-06-10

  The present invention relates to compounds of formula (I); compositions comprising the compounds, and methods of using the compounds to treat or prevent pain, diabetes, a diabetic complication, impaired glucose tolerance (IGT) or impaired fasting glucose (IGT) in a patient.