3-Allyloxy-2-(2,4-dimethoxy-phenyl)-3H-benzoimidazole-5-carboxylic acid allyl-(2,4-dimethoxy-benzyl)-amide | 498539-30-3

• 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: 3-Allyloxy-2-(2,4-dimethoxy-phenyl)-3H-benzoimidazole-5-carboxylic acid allyl-(2,4-dimethoxy-benzyl)-amide
• 英文别名: 2-(2,4-dimethoxyphenyl)-N-[(2,4-dimethoxyphenyl)methyl]-3-prop-2-enoxy-N-prop-2-enylbenzimidazole-5-carboxamide
• CAS: 498539-30-3
• 化学式: C₃₁H₃₃N₃O₆
• 分子量: 543.62
• InChiKey: QWFXWOTYDFNCIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  722.7±70.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-Allyloxy-2-(2,4-dimethoxy-phenyl)-3H-benzoimidazole-5-carboxylic acid allyl-(2,4-dimethoxy-benzyl)-amide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-Allyloxy-2-(2,4-dimethoxy-phenyl)-3H-benzoimidazole-5-carboxylic acid allylamide
  参考文献：
  名称：

  Synthesis of N-alkoxybenzimidazoles and N-alkoxypyrimidazoles

  摘要：

  A variety of novel N-alkoxy aromatic-fused imidazoles have been prepared in a simple two-step process from 2-fluoro nitroaromatics and 2-chloro-3-nitropyridine. The imidazole forming step involves tandem heterocyclisation and O-alkylation with an in situ alkylating agent, and supports prior mechanistic proposals. Additional mechanistic experiments are described. The protocol is versatile with respect to both substrate halo-nitro aromatics and to the nature of the added electrophile (halides) used in the second step, and thereby significantly extends the scope of this reaction and its applicability to diverse synthesis. This methodology can also be used to generate various types of novel N-alkoxypyrimidazoles (4-deazapurine analogues), and an X-ray structure of one such pyrimidazole is presented. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01841-5
• 作为产物：
  描述：

  N-Allyl-N-(2,4-dimethoxy-benzyl)-4-fluoro-3-nitro-benzamide 在 sodium hydride 、 potassium carbonate 作用下， 生成 3-Allyloxy-2-(2,4-dimethoxy-phenyl)-3H-benzoimidazole-5-carboxylic acid allyl-(2,4-dimethoxy-benzyl)-amide
  参考文献：
  名称：

  Synthesis of N-alkoxybenzimidazoles and N-alkoxypyrimidazoles

  摘要：

  A variety of novel N-alkoxy aromatic-fused imidazoles have been prepared in a simple two-step process from 2-fluoro nitroaromatics and 2-chloro-3-nitropyridine. The imidazole forming step involves tandem heterocyclisation and O-alkylation with an in situ alkylating agent, and supports prior mechanistic proposals. Additional mechanistic experiments are described. The protocol is versatile with respect to both substrate halo-nitro aromatics and to the nature of the added electrophile (halides) used in the second step, and thereby significantly extends the scope of this reaction and its applicability to diverse synthesis. This methodology can also be used to generate various types of novel N-alkoxypyrimidazoles (4-deazapurine analogues), and an X-ray structure of one such pyrimidazole is presented. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01841-5