N-Diethylaminomethyl-benzimidazol | 72732-15-1

• 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: N-Diethylaminomethyl-benzimidazol
• 英文别名: 1-Diethylaminomethyl-benzimidazol；1-((diethylamino)-methyl)-benzimidazole；N,N-diethylaminomethyl-1H-benzimidazole；N-((1H-benzo[d]imidazol-1-yl)methyl)-N-ethylethanamine；1-Diaethylaminomethyl-1H-benzimidazol；benzoimidazol-1-ylmethyl-diethyl-amine；N-(benzimidazol-1-ylmethyl)-N-ethylethanamine
• CAS: 72732-15-1
• 化学式: C₁₂H₁₇N₃
• mdl: MFCD01312151
• 分子量: 203.287
• InChiKey: AKDMRCSMKPFUQM-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124 °C(Solv: ethanol (64-17-5))
• 沸点：
  157 °C
• 密度：
  1.0710 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯并咪唑 、 diethyl(methoxymethyl)amine 在 hafnium tetrakis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 0.2h， 以99%的产率得到N-Diethylaminomethyl-benzimidazol
  参考文献：
  名称：

  Hf(OTf)₄-Catalyzed Regioselective N-Aminomethylation of Indoles and Related NH-Containing Heterocycles

  摘要：

  Under Lewis acidic conditions using Hf(OTf)(4), the aminomethylation of an indole derivative with a typical N,O-acetal preferentially produced kinetically favored N-aminomethylated indole derivatives instead of thermodynamically favored 3-aminomethylated indoles.

  DOI：

  10.1021/jo1006043

文献信息

• The Condensation of Aldehydes and Amines with Nitrogenous Five-atom Ring Systems¹
  作者：G. Bryant Bachman、Lowell V. Heisey

  DOI：10.1021/ja01216a018

  日期：1946.12
• Fadda; Etman; Ali, Pharmazie, 1991, vol. 46, # 1, p. 52 - 53
  作者：Fadda、Etman、Ali

  DOI：——

  日期：——
• Murti, Yogesh; Arora, Rashmi; Pathak, Devender, Journal of the Indian Chemical Society, 2010, vol. 87, # 5, p. 627 - 631
  作者：Murti, Yogesh、Arora, Rashmi、Pathak, Devender

  DOI：——

  日期：——
• Synthesis, pharmacological screening, quantum chemical and in vitro permeability studies of N-Mannich bases of benzimidazoles through bovine cornea
  作者：E. Philip Jesudason、S.K. Sridhar、E.J. Padma Malar、P. Shanmugapandiyan、Mohammed Inayathullah、V. Arul、D. Selvaraj、R. Jayakumar

  DOI：10.1016/j.ejmech.2008.03.043

  日期：2009.5

  A novel series of N-Mannich bases of benzimidazole derivatives were synthesized and characterized by H-1 NMR, IR spectral studies and elemental analysis. The compounds were screened for analgesic and anti-inflammatory activity. 1-((Diethylamino)-methyl)-2-styryl benzimidazole 4 at 40 mg/kg was found to be equipotent to paracetamol. 1-((Piperidin-1-yl) methyl)-2-styryl-benzimidazole 6 at 40 mg/kg was found to be more potent than Diclofenac. Corneal permeability and quantum chemical calculations were performed to correlate the hydrogen bonding ability with permeability and activity. The energies of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) were correlated with pharmacological activity. The semi-empirical PM3 calculations (quantum chemical calculations) revealed that E-LUMO and energy gap Delta E were capable of accounting for the high in vitro bovine corneal permeability and activity of the compounds. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Hf(OTf)₄-Catalyzed Regioselective <i>N</i>-Aminomethylation of Indoles and Related NH-Containing Heterocycles
  作者：Norio Sakai、Kazuyori Shimamura、Reiko Ikeda、Takeo Konakahara

  DOI：10.1021/jo1006043

  日期：2010.6.4

  Under Lewis acidic conditions using Hf(OTf)(4), the aminomethylation of an indole derivative with a typical N,O-acetal preferentially produced kinetically favored N-aminomethylated indole derivatives instead of thermodynamically favored 3-aminomethylated indoles.