1-propargyl-2-[(methyl-isoxazol-3-yl)methyl]benzimidazole | 918890-10-5

• 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-propargyl-2-[(methyl-isoxazol-3-yl)methyl]benzimidazole
• 英文别名: 2-[(5-Methyl-1,2-oxazol-3-yl)methyl]-1-(prop-2-yn-1-yl)-1H-benzimidazole；5-methyl-3-[(1-prop-2-ynylbenzimidazol-2-yl)methyl]-1,2-oxazole
• CAS: 918890-10-5
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: UNFWSGKOVHMDDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-propargyl-2-[(methyl-isoxazol-3-yl)methyl]benzimidazole 、 N-苯基苯羰基亚肼酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以38%的产率得到N'-(N-[4-(5-methyl-1,2-oxazol-3-yl)-2,5-diphenylpyrazol-3-yl]anilino)-N-[2-(prop-2-ynylamino)phenyl]benzenecarboximidamide
  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 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 26.0h， 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

文献信息

• Unexpected opening of benzimidazole derivatives during 1,3-dipolar cycloaddition
  作者：Brahim El Azzaoui、Bouhfid Rachid、Mohamadou Lamine Doumbia、El Mokhtar Essassi、Heinz Gornitzka、Jacques Bellan

  DOI：10.1016/j.tetlet.2006.10.071

  日期：2006.12

  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.