1-(benzyl)-4,5,6,7-tetrahydro-1H-benzimidazole-2-carboxylic acid methyl ester | 675123-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(benzyl)-4,5,6,7-tetrahydro-1H-benzimidazole-2-carboxylic acid methyl ester
• 英文别名: Methyl 1-benzyl-4,5,6,7-tetrahydrobenzimidazole-2-carboxylate
• CAS: 675123-13-4
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: NKZZSRRMGLWTNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1-(benzyl)-4,5,6,7-tetrahydro-1H-benzimidazole-2-carboxylic acid methyl ester 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以56%的产率得到3-benzyl-2-methoxycarbonyl-1,3-diazaspiro[4.4]non-1-en-4-one
  参考文献：
  名称：

  Oxidative Rearrangement of Imidazoles with Dimethyldioxirane

  摘要：

  Tetrahydrobenzimidazoles, on treatment with dimethyldioxirane, rearrange to provide 5-imidazolones exclusively. These rearrangements proceed with a broad range of substrates and with good to excellent levels of diastereoselectivity.

  DOI：

  10.1021/ol036403w
• 作为产物：
  描述：

  4,5,6,7-四氢-1H-苯并咪唑 在 sodium hydride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.5h， 生成 1-(benzyl)-4,5,6,7-tetrahydro-1H-benzimidazole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Oxidative Rearrangement of Imidazoles with Dimethyldioxirane

  摘要：

  Tetrahydrobenzimidazoles, on treatment with dimethyldioxirane, rearrange to provide 5-imidazolones exclusively. These rearrangements proceed with a broad range of substrates and with good to excellent levels of diastereoselectivity.

  DOI：

  10.1021/ol036403w

文献信息

• Oxidative Rearrangement of Imidazoles with Dimethyldioxirane
  作者：Carl J. Lovely、Hongwang Du、Yong He、H. V. Rasika Dias

  DOI：10.1021/ol036403w

  日期：2004.3.1

  Tetrahydrobenzimidazoles, on treatment with dimethyldioxirane, rearrange to provide 5-imidazolones exclusively. These rearrangements proceed with a broad range of substrates and with good to excellent levels of diastereoselectivity.
• Oxidative reactions of tetrahydrobenzimidazole derivatives with N-sulfonyloxaziridines
  作者：Rasapalli Sivappa、Panduka Koswatta、Carl J. Lovely

  DOI：10.1016/j.tetlet.2007.06.088

  日期：2007.8

  An investigation of the utility of N-sulfonyloxaziridines to effect the oxidative rearrangement of tetrahydrobenzimidazoles to spiro fused 5-imidazolones is reported. In addition to the anticipated rearrangement manifold, it was found that 2-amino substituted derivatives afford products resulting from rearrangement, or alternatively from addition of methanol or water depending on the nature of the N-substituents and reaction conditions. (c) 2007 Elsevier Ltd. All rights reserved.