2-amino-3-(3'-methylphenyl)-5-nitrobenzofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-amino-3-(3'-methylphenyl)-5-nitrobenzofuran
• 英文别名: 3-(3-Methylphenyl)-5-nitro-1-benzofuran-2-amine
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: LAMGQHNAHKBODX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间甲基苯乙腈 、 2-氯-4-硝基苯酚 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以36%的产率得到2-amino-3-(3'-methylphenyl)-5-nitrobenzofuran
  参考文献：
  名称：

  The reaction of 2-chloro-4-nitrophenol and the isomeric chloronitrobenzenes with LDA under aryne-forming conditions

  摘要：

  The unprecedented base-initiated generation of a nitrobenzyne and subsequent addition of preformed arylacetonitrile anion nucleophiles is reported. In all cases, 2-amino-5-nitro-3-benzo[b]furans are obtained as major product with small amounts of 3-arylmethyl-2-cyano-4-nitrophenols. A mechanism involving ring closure of phenoxide and nitrile groups of the initial aryne-nitrile anion adduct is proposed to account for the formation of the benzofurans. The three isomeric chloronitrobenzynes,however, do not give aryne products when treated with LDA, but rather are reduced to the corresponding bis-dichloroazoxybenzenes. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00971-5

文献信息

• The reaction of 2-chloro-4-nitrophenol and the isomeric chloronitrobenzenes with LDA under aryne-forming conditions
  作者：Sagun Tandel、Anlai Wang、Terra C Holdeman、Hongming Zhang、Edward R Biehl

  DOI：10.1016/s0040-4020(98)00971-5

  日期：1998.12

  The unprecedented base-initiated generation of a nitrobenzyne and subsequent addition of preformed arylacetonitrile anion nucleophiles is reported. In all cases, 2-amino-5-nitro-3-benzo[b]furans are obtained as major product with small amounts of 3-arylmethyl-2-cyano-4-nitrophenols. A mechanism involving ring closure of phenoxide and nitrile groups of the initial aryne-nitrile anion adduct is proposed to account for the formation of the benzofurans. The three isomeric chloronitrobenzynes,however, do not give aryne products when treated with LDA, but rather are reduced to the corresponding bis-dichloroazoxybenzenes. (C) 1998 Elsevier Science Ltd. All rights reserved.