3-(2-Aminophenyl)isocoumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-(2-Aminophenyl)isocoumarin
• 英文别名: 3-(2-Aminophenyl)isochromen-1-one
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: AXCMQTDAZWPAKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基苯乙炔 、 2-碘苯甲酸 在 四(三苯基膦)钯 三乙胺 、 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到3-(2-Aminophenyl)isocoumarin
  参考文献：
  名称：

  Synthesis of Isocoumarins from o-Iodobenzoic Acid and Terminal Acetylenes Mediated by Palladium Complexes and Zinc Chloride

  摘要：

  o-Iodobenzoic acid (1) reacts with various terminal acetylenes (HC=CR) in the presence of Pd(PPh(3))(4), Et(3)N, and ZnCl2 in DMF to give the corresponding 3-substituted isocoumarins (C6H4COOC(R)CH: R = n-C4H9 (2a); n-C3H7 (3a); CH2OCH3 (4a); C(CH3)(2)OH (5a); CH2OH (6a); C6H5 (7a);p-CH3C6H4 (8a); 1-cyclohexenyl (9a); o-NH2C6H4 (10a)) in fair to excellent yields, In some of these catalytic reactions, substituted isocoumarin b (C6H4COOC(R)C(C=CR)) and alkylidenephthalide c were isolated in a few percent yields, Under similar conditions, treatment of 1 with a trimethylsilyl 1,3-diyne 12 led to the formation of products 3-(2-indolyl)isocoumarin (13) and an indolylphthalide 14 in a 95:5 ratio. The reaction of o-1-pentynylbenzoic acid with ZnCl2 and Et(3)N gave 3a as the sole product indicating that ZnCl2 is likely responsible for the selective formation of the six-membered isocoumarin ring, Based on this observation and the known palladium chemistry, a mechanism involving the participation of palladium complexes in the alkynylation of 1 and zinc chloride in the heteroannulation of the reaction intermediate o-1-alkynylbenzoate is proposed for the present catalytic reactions.

  DOI：

  10.1021/jo00117a023

文献信息

• Synthesis of Isocoumarins from o-Iodobenzoic Acid and Terminal Acetylenes Mediated by Palladium Complexes and Zinc Chloride
  作者：Hong-Yueh Liao、Chien-Hong Cheng

  DOI：10.1021/jo00117a023

  日期：1995.6

  o-Iodobenzoic acid (1) reacts with various terminal acetylenes (HC=CR) in the presence of Pd(PPh(3))(4), Et(3)N, and ZnCl2 in DMF to give the corresponding 3-substituted isocoumarins (C6H4COOC(R)CH: R = n-C4H9 (2a); n-C3H7 (3a); CH2OCH3 (4a); C(CH3)(2)OH (5a); CH2OH (6a); C6H5 (7a);p-CH3C6H4 (8a); 1-cyclohexenyl (9a); o-NH2C6H4 (10a)) in fair to excellent yields, In some of these catalytic reactions, substituted isocoumarin b (C6H4COOC(R)C(C=CR)) and alkylidenephthalide c were isolated in a few percent yields, Under similar conditions, treatment of 1 with a trimethylsilyl 1,3-diyne 12 led to the formation of products 3-(2-indolyl)isocoumarin (13) and an indolylphthalide 14 in a 95:5 ratio. The reaction of o-1-pentynylbenzoic acid with ZnCl2 and Et(3)N gave 3a as the sole product indicating that ZnCl2 is likely responsible for the selective formation of the six-membered isocoumarin ring, Based on this observation and the known palladium chemistry, a mechanism involving the participation of palladium complexes in the alkynylation of 1 and zinc chloride in the heteroannulation of the reaction intermediate o-1-alkynylbenzoate is proposed for the present catalytic reactions.