4-[N-(3-chlorophenyl)amino]-3-(N-cyclohexylamino)-1H-isochromen-1-one | 1208940-82-2

• 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: 4-[N-(3-chlorophenyl)amino]-3-(N-cyclohexylamino)-1H-isochromen-1-one
• 英文别名: 4-(3-Chloroanilino)-3-(cyclohexylamino)isochromen-1-one；4-(3-chloroanilino)-3-(cyclohexylamino)isochromen-1-one
• CAS: 1208940-82-2
• 化学式: C₂₁H₂₁ClN₂O₂
• 分子量: 368.863
• InChiKey: ZMAJNTKKVYJATL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[N-(3-chlorophenyl)amino]-3-(N-cyclohexylamino)-1H-isochromen-1-one 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.03h， 以100%的产率得到N-cyclohexyl-2-(3-chlorophenyl)-1,3-dihydro-1-oxoisoindol-3-carboxamide
  参考文献：
  名称：

  Isolation of Ugi Four-Component Condensation Primary Adducts: A Straightforward Route to Isocoumarins

  摘要：

  Ugi four-component condensation (Ugi-4CC) between 2-formylbenzoic acid, phenacylamine dimethyl acetal, and isocyanides afforded 1H-isochromen-1-ones (isocoumarins). These products, where structure corresponds to the tautomeric enediamine form of the Ugi-4CC primary adducts, were stable enough to allow their isolation and characterization. Stable isocoumarins were also obtained by employing anilines as the amino component in the Ugi four-component condensation.

  DOI：

  10.1021/ol9028622
• 作为产物：
  描述：

  异氰环已烷 、 3-氯苯胺 、 邻羧基苯甲醛 以 甲醇 为溶剂， 反应 1.0h， 以62%的产率得到4-[N-(3-chlorophenyl)amino]-3-(N-cyclohexylamino)-1H-isochromen-1-one
  参考文献：
  名称：

  Isolation of Ugi Four-Component Condensation Primary Adducts: A Straightforward Route to Isocoumarins

  摘要：

  Ugi four-component condensation (Ugi-4CC) between 2-formylbenzoic acid, phenacylamine dimethyl acetal, and isocyanides afforded 1H-isochromen-1-ones (isocoumarins). These products, where structure corresponds to the tautomeric enediamine form of the Ugi-4CC primary adducts, were stable enough to allow their isolation and characterization. Stable isocoumarins were also obtained by employing anilines as the amino component in the Ugi four-component condensation.

  DOI：

  10.1021/ol9028622

文献信息

• Synthesis of diverse phenylglycine derivatives via transformation of Ugi four-component condensation primary adducts
  作者：Stefano Marcaccini、Gloria Menchi、Andrea Trabocchi

  DOI：10.1016/j.tetlet.2011.03.074

  日期：2011.5

  3-(N-Substituted)amino-4-arylamino-1H-isochromenones (isocoumarins) which can be regarded as the enediamine tautomers of the Ugi four-component condensation primary adducts between 2-formylbenzoic acids, arylamines, and isocyanides undergo a facile ring cleavage with amines to give a series of phenylglycine derivatives. Thus, a synthetically useful post-condensation transformation of Ugi four-component

  3-（N-取代的）氨基-4-芳基氨基-1 H-异色酮（异香豆素）可以被视为Ugi四甲酰苯甲酸，芳基胺和异氰酸酯之间的四组分缩合伯加合物的烯二胺互变异构体用胺进行环裂解，得到一系列苯基甘氨酸衍生物。因此，首次描述了Ugi四组分缩合初级加合物的合成有用的缩合后转化。
• Isolation of Ugi Four-Component Condensation Primary Adducts: A Straightforward Route to Isocoumarins
  作者：Cristina Faggi、María García-Valverde、Stefano Marcaccini、Gloria Menchi

  DOI：10.1021/ol9028622

  日期：2010.2.19

  Ugi four-component condensation (Ugi-4CC) between 2-formylbenzoic acid, phenacylamine dimethyl acetal, and isocyanides afforded 1H-isochromen-1-ones (isocoumarins). These products, where structure corresponds to the tautomeric enediamine form of the Ugi-4CC primary adducts, were stable enough to allow their isolation and characterization. Stable isocoumarins were also obtained by employing anilines as the amino component in the Ugi four-component condensation.