(9ci)-1-乙基-alpha-甲基-1H-苯并咪唑-2-甲醇 | 299936-69-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (9ci)-1-乙基-alpha-甲基-1H-苯并咪唑-2-甲醇
• 英文名称: N-ethyl-2-(α-hydroxyethyl)benzimidazole
• 英文别名: 1-(1-Ethylbenzimidazol-2-yl)ethan-1-ol；1-(1-ethylbenzimidazol-2-yl)ethanol
• CAS: 299936-69-9
• 化学式: C₁₁H₁₄N₂O
• mdl: MFCD01547011
• 分子量: 190.245
• InChiKey: JDTYBLPYFVFWHB-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  352.2±25.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (9ci)-1-乙基-alpha-甲基-1H-苯并咪唑-2-甲醇 在 溶剂黄146 、 bis(2-methyl-1H-benzimidazolinium) dichromate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以89%的产率得到1-(1-乙基-1H-苯并咪唑-2-基)乙酮
  参考文献：
  名称：

  Ramaiah; Dubey; Ramanatham, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1765 - 1767

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(1-乙基-1H-苯并咪唑-2-基)乙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以69%的产率得到(9ci)-1-乙基-alpha-甲基-1H-苯并咪唑-2-甲醇
  参考文献：
  名称：

  Alternate Method for the Synthesis of N‐Alkyl/aralkyl‐2‐(α‐hydroxy Alkyl/aralkyl)benzimidazoles via Regiospecific Acetylation

  摘要：

  Acetylation of 1H-2-(alpha-hydroxyalkyl/aryl) benzimidazoles 2 with Ac2O results in the regiospecific formation of O-acetoxy derivative 3, which on alkylation with alkylating agents in nonaqueous media under phase-transfer catalytic conditions affords N-alkyl derivatives 4. The latter, on hydrolysis in an aqueous basic medium, results in the title compounds 5 in good yields in high purity. Alternatively, 5 can also be obtained by reduction of 1-substituted-2-acetyl/benzoylbenzimidazoles 8 using NaBH4.

  DOI：

  10.1080/00397910701265556

文献信息

• Synthesis and in vitro antifungal evaluation of benzoimidazolyl-piperazinyl-phenylmethanone derivatives.
  作者：Rani S Kankate、Parag S Gide、Deepak P Belsare

  DOI：10.13005/ojc/300446

  日期：2014.12.31

  Benzimidazole and piperazines are the important pharmacophores in the structures of many antifungal compounds. Further, the phenylmethanone are also a unique class of compounds whose antifungal profile is not much exploited. So to exploit their antifungal potential we have selected these three combinations and framed the novel parent structure for our research work. In this study a novel series of benzimidazoles derivatives was synthesized by microwave irradiation and characterized by 1H NMR, 13C NMR, Infra Red (IR), and Mass Spectroscopy (MS), and by elemental analysis. The screening of compound for in vitro (turbidimetric method) antifungal activity against C.albicans revealed activity in many of the compounds as comparable to that of ketoconazole.

  苯并咪唑和哌嗪是许多抗真菌化合物结构中的重要药效团。此外，苯甲酮也是一类独特的化合物，其抗真菌特性尚未得到充分开发。为了挖掘其抗真菌潜力，我们选择了这三种组合，并为我们的研究工作构建了新型母体结构。在本研究中，通过微波辐射合成了系列新型苯并咪唑衍生物，并通过1H NMR、13C NMR、红外（IR）和质谱（MS）以及元素分析进行了表征。对化合物进行体外（浊度计法）抗真菌活性筛选，针对白色念珠菌（C.albicans）的活性测试显示，许多化合物的活性可与酮康唑相媲美。
• Dubey; Kumar, C. Ravi; Babu, Balaji, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 12, p. 3128 - 3130
  作者：Dubey、Kumar, C. Ravi、Babu, Balaji

  DOI：——

  日期：——
• Investigations of unsaturated azoles. 13. Synthesis and some reactions of 1-alkylbenzimidazoles
  作者：I. I. Popov

  DOI：10.1007/bf01164866

  日期：1996.6
• [EN] PYRAZOLOPYRIDINONE COMPOUNDS<br/>[FR] COMPOSÉS PYRAZOLOPYRIDINONES
  申请人：[en]BEIGENE, LTD.

  公开号：WO2023011456A1

  公开（公告）日：2023-02-09

  Disclosed herein is a compound of Formula (I) for activating T cells, promoting T cell proliferation, and/or exhibiting antitumor activity, a method of using the compounds disclosed herein for treating cancer, and a pharmaceutical composition comprising the same.
• Alternate Method for the Synthesis of N‐Alkyl/aralkyl‐2‐(α‐hydroxy Alkyl/aralkyl)benzimidazoles via Regiospecific Acetylation
  作者：P. K. Dubey、P.V.V. Prasada Reddy、K. Srinivas

  DOI：10.1080/00397910701265556

  日期：2007.5.1

  Acetylation of 1H-2-(alpha-hydroxyalkyl/aryl) benzimidazoles 2 with Ac2O results in the regiospecific formation of O-acetoxy derivative 3, which on alkylation with alkylating agents in nonaqueous media under phase-transfer catalytic conditions affords N-alkyl derivatives 4. The latter, on hydrolysis in an aqueous basic medium, results in the title compounds 5 in good yields in high purity. Alternatively, 5 can also be obtained by reduction of 1-substituted-2-acetyl/benzoylbenzimidazoles 8 using NaBH4.