2-乙酰氧基甲基-1-甲基-1H-苯并咪唑 | 14484-09-4

• 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: 2-乙酰氧基甲基-1-甲基-1H-苯并咪唑
• 英文名称: (1-methyl-1H-benzo[d]imidazol-2-yl)methyl acetate
• 英文别名: 1-Methyl-2-acetoxymethyl-benzimidazol；2-Acetoxymethyl-1-methyl-benzimidazol；2-acetoxymethyl-1-methyl-1H-benzoimidazole；acetic acid-(1-methyl-1H-benzimidazol-2-ylmethyl ester)；Essigsaeure-(1-methyl-1H-benzimidazol-2-ylmethylester)；(1-Methylbenzimidazol-2-yl)methyl acetate
• CAS: 14484-09-4
• 化学式: C₁₁H₁₂N₂O₂
• mdl: MFCD25959068
• 分子量: 204.228
• InChiKey: KHVMIEMUCBWVMY-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69 °C
• 沸点：
  361.8±25.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-乙酰氧基甲基-1-甲基-1H-苯并咪唑 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以76%的产率得到(1-甲基-1H-苯并咪唑-2-基)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
• 作为产物：
  描述：

  2-羟甲基苯并咪唑 在 甲醇 、 溶剂黄146 作用下， 生成 2-乙酰氧基甲基-1-甲基-1H-苯并咪唑
  参考文献：
  名称：

  Sacharowa et al., Zhurnal Obshchei Khimii, 1953, vol. 23, p. 1225,1229; engl. Ausg. S. 1289, 1292

  摘要：

  DOI：

文献信息

• Selective C–H trifluoromethylation of benzimidazoles through photoredox catalysis
  作者：Guo-Lin Gao、Chao Yang、Wujiong Xia

  DOI：10.1039/c6cc08975e

  日期：——

  This protocol presented a new strategy for visible-light induced C-H trifluoromethyltion at C4 of benzimidazoles using Togini's reagent in the presense of fac-Ir(ppy)3. It's Highlighted by its operational simplicity, mild...

  该协议提出了一种新的策略，以fac-Ir（ppy）3为代表，使用Togini试剂在苯并咪唑的C4处引起CH三氟甲基CH的三氟甲基化反应。它以其操作简单，温和而着称。
• Synthesis, Cytotoxicity, and DNA Interactions of New Cisplatin Analogues Containing Substituted Benzimidazole Ligands
  作者：Fatma Gümüş、Gökçen Eren、Leyla Açık、Ayten Çelebi、Fatma Öztürk、Şükran Yılmaz、Rahşan Ilıkçı Saǧkan、Sibel Gür、Aykut Özkul、Ayhan Elmalı、Yalçın Elerman

  DOI：10.1021/jm8000983

  日期：2009.3.12

  Six new platinum(II) complexes with 1-H or methyl-2-chloromethyl or acetoxymethyl or 2'-hydroxyethylbenzimidazole carrier ligands were synthesized and evaluated for their reactivity against model nucleophile I-, cellular uptake, and in vitro anti proliferative activities against the human MCF-7 breast and HeLa cervix cancer cell lines. The effect of the compounds on pBR322 plasmid DNA was studied by gel electrophoretic mobility measurements. Flow cytometric analysis was also carried out to study the effect of representative compounds 1 and 2, bearing 2-chloromethyl or -acetoxymethylbenzimidazole carrier ligands, on the cell cycle distribution of MCF-7 and HeLa cells, respectively. In general, it was found that Pt(II) complexes were less cytotoxic than cisplatin and were comparable to carboplatin. The results of the plasmid DNA interaction and the restriction studies suggest that changing the chemical structure of the benzimidazole ligands may modulate DNA binding mode and the sequence selectivity. Compounds I and 2 had no significant effect on the cell cycle profile of the cells used. However, Compound 2 induced a significant increase in the SubG1 cell population at a concentration of 20 mu M.