(1-methyl-1H-benzo[d]imidazol-2-yl)(phenyl)methanol | 17452-05-0

• 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: (1-methyl-1H-benzo[d]imidazol-2-yl)(phenyl)methanol
• 英文别名: (1-methyl-1H-benzoimidazol-2-yl)-phenyl-methanol；(1-methyl-1H-benzimidazol-2-yl)(phenyl)methanol；(1-methylbenzimidazol-2-yl)-phenylmethanol
• CAS: 17452-05-0
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: XYXZIVDSZIRGFM-UHFFFAOYSA-N

物化性质

• 熔点：
  157 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  459.1±38.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  (1-methyl-1H-benzo[d]imidazol-2-yl)(phenyl)methanol 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 18.0h， 生成 2-(methoxy(phenyl)methyl)-1,3-dimethyl-1H-benzo[d]imidazol-3-ium triflate
  参考文献：
  名称：

  O-甲基化布雷斯洛中间体的结构和反应活性

  摘要：

  尽可能接近：由于Breslow中间体通常以酮形式存在，因此其O保护的互变异构体可能被视为与其最接近的可分离亲戚。已经合成了一系列这些化合物，确定了它们的结构，并研究了它们与亲电试剂的反应动力学。

  DOI：

  10.1002/anie.201204524
• 作为产物：
  描述：

  2-(羟基苯基甲基)苯并咪唑 在 sodium hydroxide 、 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.5h， 生成 (1-methyl-1H-benzo[d]imidazol-2-yl)(phenyl)methanol
  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。
• Formation of Deoxybenzoins from 1,3-Dimethyl-2-(.ALPHA.-benzyloxybenzyl)benzimidazolium Iodides through Rearrangement Followed by Expulsion of Azolium Ylide.
  作者：Akira MIYASHITA、Yoshiyuki MATSUOKA、Ken-ichi IWAMOTO、Takeo HIGASHINO

  DOI：10.1248/cpb.42.1960

  日期：——

  Treatment of several 1, 3-dimethyl-2-(α-benzyloxybenzyl)benzimidazolium iodides 1 with K2CO3 gave deoxybenzoins 2 in moderate yields. Deoxybenzoins 2 were produced through rearrangement of benzyl groups followed by expulsion of 1, 3-dimethylbenzimidazolium ylide (4). The reaction is classified as a Witting rearrangement.

  几个1, 3-二甲基-2-(α-苄氧基苯基)苯并咪唑铵碘化物1与K2CO3反应，得到较为适中的产率的去氧苯酮2。去氧苯酮2是通过苄基的重排后排除1, 3-二甲基苯并咪唑铵耦合物（4）生成的。该反应被归类为Witting重排反应。
• A New Method of Synthesizing Deoxybenzoins from 1,3-Dimethyl-2-(.ALPHA.-benzyloxybenzyl)imidazolium and 1,3-Dimethyl-2-(.ALPHA.-benzyloxybenzyl)benzimidazolium Iodides Based on Wittig-Type Rearrangement.
  作者：Akira MIYASHITA、Yoshiyuki MATSUOKA、Yumiko SUZUKI、Ken-ichi IWAMOTO、Takeo HIGASHINO

  DOI：10.1248/cpb.45.1235

  日期：——

  The treatment of 1, 3-dimethyl-2-(α-benzyloxybenxyl)benzimidazolium iodides 1 with a base gave deoxybenzoins 2 in moderate yields. Sodium hydride (NaH), potassium carbonate (K2CO3), and cesium carbonate (Cs2CO3) were effective bases in this reaction. Deoxybenzoins 2 were produced through rearrangement of the benzyl group followed by expulsion of the 1, 3-dimethylbenzimidazolium ylide (A). The rearrangement proceeds in a way similar to Witting rearrangement. Deoxybenzoins 2 were also formed in good yields from 1, 3-dimethyl-2-(α-benzyloxybenxyl)-imidazolium iodides 4 upon similar treatment. However, the quaternary salts having a thiazolium moiety 5a and a pyridinium moiety 6a failed to produce deoxybenzoin (2a).

  对1, 3-二甲基-2-(α-苄氧苄基)苯并咪唑铵碘化物1进行碱性处理后，得到中等产率的去氧苄酮2。氢化钠（NaH）、碳酸钾（K2CO3）和碳酸铯（Cs2CO3）在此反应中是有效的碱。去氧苄酮2是通过苄基的重排，随后排出1, 3-二甲基苯并咪唑铵烯体（A）而生成的。该重排过程类似于维廷重排。对1, 3-二甲基-2-(α-苄氧苄基)-咪唑铵碘化物4进行类似处理时，去氧苄酮2也以良好的产率形成。然而，具有噻唑铵基团5a和吡啶铵基团6a的季铵盐未能产生去氧苄酮（2a）。
• Synthesis and Reactivities of 1,3-Dimethyl-2-(a-hydroxybenzyl)imidazolium and 1,3-Dimethyl-2-(a-hydroxybenzyl)benzimidazolium Iodides
  作者：Akira Miyashita、Akihito Kurachi、Yoshiyuki Matsuoka、Noriko Tanabe、Yumiko Suzuki、Ken-ichi Iwamoto、Takeo Higashino

  DOI：10.3987/com-96-s40

  日期：——

  1,3-Dimethyl-2-(alpha-hydroxybenzyl)benzimidazolium iodide (3a) was synthesized from 1-methylbenzimidazole (10) through two steps involving lithiation and quaternization. Treatment of 3a with 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (6) afforded 4-benzoyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (15a). 4-Benzoylquinazoline (14a) and 7-benzoyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (16a) were given by reaction of 3a with 4-chloroquinazolin (5) and 7-chloro-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine. (7). Treatment of 3a with benzaldehyde (9a) gave benzoin (8a). Similar results were obtained in the reactions of 1,3-dimethyl-2-(alpha-hydroxybenzyl)imidazo iodide (4a).
• Formation of ?-(1-methyl-2-benzimidazolyl)benzyl benzoates by the combined action of aromatic aldehydes and acyl halides on 1-methylbenzimidazole
  作者：B. I. Khristich、A. M. Simonov、O. I. Roslyakova

  DOI：10.1007/bf00516467

  日期：1983.8