3-benzyl-2-cyano-4,5-dimethoxybenzoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzyl-2-cyano-4,5-dimethoxybenzoic acid
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: ICIUMHAIUQBNHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-溴-4,5-二甲氧基苯甲酸 、 苯乙腈 在 lithium diisopropyl amide 作用下， 生成 藜芦酸 、 3-benzyl-2-cyano-4,5-dimethoxybenzoic acid 、 3-[Cyano(phenyl)methyl]-4,5-dimethoxybenzoic acid
  参考文献：
  名称：

  Preparation of 2-Cyanobenzoic Acids from the Reaction of Bromobenzoic Acids with Arylacetonitriles and LDA

  摘要：

  The reaction of various bromobenzoic acids 1 with arylacetonitriles 3 in the presence of LDA at -70 degrees C gave predominantly 2-cyanobenzoic acids 4 plus minor amounts of 3-(arylcyanomethyl)benzoic acids 5 and debrominated benzoic acids 6. The reaction is thought to proceed through a benzyne-3-carboxylate intermediate 2, which is formed at -70 degrees C upon the addition of the arylacetonitrile 3 to a solution of the appropriate lithium halobenzoate and excess LDA. The base-initiated generation of an aryne intermediate from a haloarene at such low temperatures is unprecedented. To confirm the orientation of the cyano and carboxylic acid groups, 4-methoxy-2-cyanobenzoic acid (4f) was converted to the corresponding anhydride (8) via phthalic acid (7) and to 3,3-dimethyl- and 3,3-di-n-butyl-2,3-dihydro-5-methoxy-4-(4-methoxyphenyl)-methyl-1H-isoindol-1-ones (9).

  DOI：

  10.1021/jo9711293

文献信息

• Preparation of 2-Cyanobenzoic Acids from the Reaction of Bromobenzoic Acids with Arylacetonitriles and LDA
  作者：Anlai Wang、John A. Maguire、Ed Biehl

  DOI：10.1021/jo9711293

  日期：1998.4.1

  The reaction of various bromobenzoic acids 1 with arylacetonitriles 3 in the presence of LDA at -70 degrees C gave predominantly 2-cyanobenzoic acids 4 plus minor amounts of 3-(arylcyanomethyl)benzoic acids 5 and debrominated benzoic acids 6. The reaction is thought to proceed through a benzyne-3-carboxylate intermediate 2, which is formed at -70 degrees C upon the addition of the arylacetonitrile 3 to a solution of the appropriate lithium halobenzoate and excess LDA. The base-initiated generation of an aryne intermediate from a haloarene at such low temperatures is unprecedented. To confirm the orientation of the cyano and carboxylic acid groups, 4-methoxy-2-cyanobenzoic acid (4f) was converted to the corresponding anhydride (8) via phthalic acid (7) and to 3,3-dimethyl- and 3,3-di-n-butyl-2,3-dihydro-5-methoxy-4-(4-methoxyphenyl)-methyl-1H-isoindol-1-ones (9).