2-[(5-methyl-isoxazol-3-yl)methyl]benzimidazole | 356789-25-8

• 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: 2-[(5-methyl-isoxazol-3-yl)methyl]benzimidazole
• 英文别名: 3-(1H-benzimidazol-2-ylmethyl)-5-methyl-1,2-oxazole
• CAS: 356789-25-8
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: VXALZPBDOVIYQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(5-methyl-isoxazol-3-yl)methyl]benzimidazole 、 3-溴丙炔 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 1-propargyl-2-[(methyl-isoxazol-3-yl)methyl]benzimidazole
  参考文献：
  名称：

  Unexpected opening of benzimidazole derivatives during 1,3-dipolar cycloaddition

  摘要：

  Hydroxylamine hydrochloride adds via a Michael reaction on the acetonylidene moiety of (4Z)-(2-oxopropylidene)1,2,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one, leading only to 2-[(5-methyl-isoxazol-3-yl)]methyl]benzimidazoles. This report describes the difference of reactivity of C-phenyl-N-phenyl formohydrazonoyl chloride with benzimidazole. For the N-substituted benzimidazole, an unexpected opening of the azole ring occurs, which was confirmed by single crystal X-ray diffraction analysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.071
• 作为产物：
  描述：

  (Z)-4-(2-oxopropylidene)-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以70%的产率得到2-[(5-methyl-isoxazol-3-yl)methyl]benzimidazole
  参考文献：
  名称：

  Unexpected opening of benzimidazole derivatives during 1,3-dipolar cycloaddition

  摘要：

  Hydroxylamine hydrochloride adds via a Michael reaction on the acetonylidene moiety of (4Z)-(2-oxopropylidene)1,2,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one, leading only to 2-[(5-methyl-isoxazol-3-yl)]methyl]benzimidazoles. This report describes the difference of reactivity of C-phenyl-N-phenyl formohydrazonoyl chloride with benzimidazole. For the N-substituted benzimidazole, an unexpected opening of the azole ring occurs, which was confirmed by single crystal X-ray diffraction analysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.071