6-bromo-2-methyl-1-phenyl-1H-benzo[d]imidazole | 112564-28-0

• 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: 6-bromo-2-methyl-1-phenyl-1H-benzo[d]imidazole
• 英文别名: 6-Bromo-2-methyl-1-phenyl-1H-benzimidazole；6-bromo-2-methyl-1-phenylbenzimidazole
• CAS: 112564-28-0
• 化学式: C₁₄H₁₁BrN₂
• 分子量: 287.159
• InChiKey: GSASJGMMCYLKRG-UHFFFAOYSA-N

物化性质

• 沸点：
  429.8±37.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  亚磷酸二乙酯 、 6-bromo-2-methyl-1-phenyl-1H-benzo[d]imidazole 在 四(三苯基膦)钯 三乙胺 作用下， 反应 14.0h， 以49%的产率得到(2-Methyl-3-phenyl-3H-benzoimidazol-5-yl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Tolmachev, A. A.; Kozlov, E. S.; Pinchuk, A. M., Journal of general chemistry of the USSR, 1986, vol. 56, p. 2214 - 2216

  摘要：

  DOI：
• 作为产物：
  描述：

  N'-(4-bromo-2-fluorophenyl)-N-phenylacetimidamide 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以83%的产率得到6-bromo-2-methyl-1-phenyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Benzimidazoles Mediated by KOH/DMSO

  摘要：

  Benzimidazoles are prepared by intramolecular N-arylations of amidines mediated by potassium hydroxide in DMSO at 120 degrees C. In this manner, diversely substituted products have been obtained in moderate to very good yields.

  DOI：

  10.1021/ol403414v

文献信息

• Access to Amidines and Arylbenzimidazoles: Zinc-Promoted Rearrangement of Oxime Acetates
  作者：Zhongzhi Zhu、Jinghe Cen、Xiaodong Tang、Jianxiao Li、Wanqing Wu、Huanfeng Jiang

  DOI：10.1002/adsc.201701490

  日期：2018.5.16

  zinc‐promoted rearrangement of oxime acetates with arylamines for the synthesis of amidines has been developed under mild conditions. This process involves N−O/C−C bond cleavages and C−C/C−N bond formations. Various oxime acetates and arylamines are suitable for this transformation. Furthermore, diverse arylbenzimidazoles could also be prepared through simple one‐pot procedure.

  在温和的条件下，已开发出一种有效且直接的锌促进肟肟与芳胺的锌促进重排以合成for的方法。此过程涉及N / O / C-C键断裂和C-C / C-N键形成。各种肟乙酸酯和芳胺适合于该转化。此外，还可以通过简单的一锅法制备各种芳基苯并咪唑。
• Metal-Free One-Pot Synthesis of<i>N</i>,<i>N′</i>-Diarylamidines and<i>N</i>-Arylbenzimidazoles from Arenediazonium Salts, Nitriles, and Free Anilines
  作者：So Won Youn、Eun Mi Lee

  DOI：10.1021/acs.orglett.6b02994

  日期：2016.11.4

  efficient and facile metal-free, one-pot reaction has been developed to afford diversely substituted N-arylbenzimidazoles through chemoselective in situ generation of N,N′-diarylamidines from arenediazonium salts, nitriles, and free anilines. The advantages of this protocol consist of the operationally easy and simple one-pot procedure under metal-free and mild conditions, the direct use of inexpensive

  已经开发了一种高效且简便的无金属单锅反应，可通过化学方法从槟榔二唑鎓盐，腈和游离苯胺中原位生成N，N'-二芳基idine胺，从而提供不同取代的N-芳基苯并咪唑。该协议的优点包括：在无金属和温和条件下操作简单，操作简单的一锅法；直接使用廉价和可商购的化学药品；因此，具有成本效益且更环保。
• TOLMACHEV A. A.; KOZLOV EH. S.; PINCHUK A. M., ZH. OBSHCH. XIMII, 56,(1986) N 11, 2503-2507
  作者：TOLMACHEV A. A.、 KOZLOV EH. S.、 PINCHUK A. M.

  DOI：——

  日期：——
• AMINOPYRIMIDINE AND AMINOTRIAZINE DERIVATIVES AS MYC PROTEIN MODULATORS
  申请人：[en]SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE

  公开号：WO2024044757A1

  公开（公告）日：2024-02-29

  The present disclosure provides compounds and compositions that are useful as MYC protein modulators and methods of using the same for treating MYC-mediated diseases or disorders.
• Transition-Metal-Free Synthesis of Benzimidazoles Mediated by KOH/DMSO
  作者：Hannah Baars、Astrid Beyer、Stefanie V. Kohlhepp、Carsten Bolm

  DOI：10.1021/ol403414v

  日期：2014.1.17

  Benzimidazoles are prepared by intramolecular N-arylations of amidines mediated by potassium hydroxide in DMSO at 120 degrees C. In this manner, diversely substituted products have been obtained in moderate to very good yields.