(5,6-dimethyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone | 16109-46-9

• 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: (5,6-dimethyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone
• 英文别名: 1-benzoyl-5,6-dimethyl-1H-benzimidazole；1-benzoyl-5,6-dimethyl-1H-benzoimidazole；1-Benzyl-5,6-dimethyl-benzimidazol；1H-Benzimidazole, 1-benzoyl-5,6-dimethyl-；(5,6-dimethylbenzimidazol-1-yl)-phenylmethanone
• CAS: 16109-46-9
• 化学式: C₁₆H₁₄N₂O
• mdl: MFCD00425222
• 分子量: 250.3
• InChiKey: DHAQHTRQAPZNJW-UHFFFAOYSA-N

物化性质

• 沸点：
  439.8±48.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5,6-dimethyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 (5,6-Bis-dibromomethyl-benzoimidazol-1-yl)-phenyl-methanone
  参考文献：
  名称：

  Defined dimensional alterations in enzyme substrates. lin-Naphthoadenine and lin-naphthoadenosine

  摘要：

  DOI：

  10.1021/jo00186a016
• 作为产物：
  描述：

  5,6-二甲基苯并咪唑 、 苯甲醛 在 二叔丁基过氧化物 作用下， 以 乙酸乙酯 为溶剂， 反应 15.0h， 以93%的产率得到(5,6-dimethyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone
  参考文献：
  名称：

  Metal-free cross-dehydrogenative coupling of benzimidazoles with aldehydes to N-acylbenzimidazoles

  摘要：

  A novel and direct cross-dehydrogenative coupling (CDC) between benzimidazoles with aldehydes promoted by di-tert-butyl peroxide (DTBP) was developed. The reactions generated the corresponding N-acylbenzimidazoles in good yields under metal-free conditions. This method has broad substrate scope and high efficiency. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.07.009

文献信息

• Chemoselective acylation of benzimidazoles with phenylacetic acids under different Cu catalysts to give fused five-membered N-heterocycles or tertiary amides
  作者：Shaoyu Mai、Yingwei Zhao、Qiuling Song

  DOI：10.1039/c6ob01167e

  日期：——

  bond formation via a copper-catalyzed aerobic oxidative decarboxylative tandem protocol was realized. The phenylacetic acids which contain ortho-X (X = F or Br) on the aromatic ring will render a fused five-membered heterocycle via a tandem aromatic nucleophilic substitution and aerobic oxidative decarboxylative acylation at the C(sp2)–H bond of benzimidazoles under the Cu(OAc)2/K2CO3/BF3·Et2O catalytic

  通过铜催化的好氧氧化脱羧串联方案实现了C–N键的形成。在芳环上含有邻-X（X = F或Br）的苯乙酸将通过串联芳族亲核取代和苯并咪唑的C（sp 2）-H键上的好氧氧化脱羧酰化反应，形成稠合的五元杂环在Cu（OAc）2 / K 2 CO 3 / BF 3 ·Et 2 O催化体系下，以CuBr为催化剂，吡啶为碱，发生N-酰化反应，得到叔酰胺。
• Metal-free cross-dehydrogenative coupling of benzimidazoles with aldehydes to N-acylbenzimidazoles
  作者：Lin Yu、Min Wang、Lei Wang

  DOI：10.1016/j.tet.2014.07.009

  日期：2014.9

  A novel and direct cross-dehydrogenative coupling (CDC) between benzimidazoles with aldehydes promoted by di-tert-butyl peroxide (DTBP) was developed. The reactions generated the corresponding N-acylbenzimidazoles in good yields under metal-free conditions. This method has broad substrate scope and high efficiency. (C) 2014 Elsevier Ltd. All rights reserved.
• Defined dimensional alterations in enzyme substrates. lin-Naphthoadenine and lin-naphthoadenosine
  作者：Thomas M. Stevenson、Nelson J. Leonard

  DOI：10.1021/jo00186a016

  日期：1984.6