4-butyryl-1-cyclohexyl-3-methyl-3,4-dihydroquinoxalin-2(1H)-one | 1139917-64-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-butyryl-1-cyclohexyl-3-methyl-3,4-dihydroquinoxalin-2(1H)-one
• 英文别名: 4-butanoyl-1-cyclohexyl-3-methyl-3H-quinoxalin-2-one
• CAS: 1139917-64-8
• 化学式: C₁₉H₂₆N₂O₂
• 分子量: 314.428
• InChiKey: SZIXCROMFXIXKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(1-(cyclohexylamino)-1-oxopropan-2-yl)-N-(2-iodophenyl)butyramide 在 caesium carbonate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到4-butyryl-1-cyclohexyl-3-methyl-3,4-dihydroquinoxalin-2(1H)-one
  参考文献：
  名称：

  Ugi-Post Functionalization, from a Single Set of Ugi-Adducts to Two Distinct Heterocycles by Microwave-Assisted Palladium-Catalyzed Cyclizations: Tuning the Reaction Pathways by Ligand Switch

  摘要：

  Linear amides 4, prepared in one step by the Ugi four-component reaction, were converted to 3,4-dihydroquinoxalin-3-ones (5) or to 2-(2-oxoindolin-1-yl)acetamides (6) dependent on the catalytic conditions. While microwave irradiation was found to be determinant on the reaction efficiency, the choice of ligand diverged the reaction pathways. Heating a solution of 4 in dioxane/MeCN (v/v = 85/ 15) under microwave irradiation conditions in the presence of Pd(dba)(2) (0.05 equiv) and CS2CO3 (2 equiv), using XPhos as a supporting ligand, afforded the 3,4-dihydroquinoxalin-3-ones (5) via an intramolecular N-arylation of the secondary amide. On the other hand, using BINAP as ligand under otherwise identical conditions, intramolecular alpha-CH arylation of tertiary amide occurred to furnish the oxindoles (6).

  DOI：

  10.1021/jo900210x

文献信息

• Ugi-Post Functionalization, from a Single Set of Ugi-Adducts to Two Distinct Heterocycles by Microwave-Assisted Palladium-Catalyzed Cyclizations: Tuning the Reaction Pathways by Ligand Switch
  作者：William Erb、Luc Neuville、Jieping Zhu

  DOI：10.1021/jo900210x

  日期：2009.4.17

  Linear amides 4, prepared in one step by the Ugi four-component reaction, were converted to 3,4-dihydroquinoxalin-3-ones (5) or to 2-(2-oxoindolin-1-yl)acetamides (6) dependent on the catalytic conditions. While microwave irradiation was found to be determinant on the reaction efficiency, the choice of ligand diverged the reaction pathways. Heating a solution of 4 in dioxane/MeCN (v/v = 85/ 15) under microwave irradiation conditions in the presence of Pd(dba)(2) (0.05 equiv) and CS2CO3 (2 equiv), using XPhos as a supporting ligand, afforded the 3,4-dihydroquinoxalin-3-ones (5) via an intramolecular N-arylation of the secondary amide. On the other hand, using BINAP as ligand under otherwise identical conditions, intramolecular alpha-CH arylation of tertiary amide occurred to furnish the oxindoles (6).