2-(N-(4-bromobiphenyl-3-yl)propionamido)-N-tert-butyl-3-methylbutanamide

• 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: 2-(N-(4-bromobiphenyl-3-yl)propionamido)-N-tert-butyl-3-methylbutanamide
• 英文别名: 2-(2-bromo-5-phenyl-N-propanoylanilino)-N-tert-butyl-3-methylbutanamide
• 化学式: C₂₄H₃₁BrN₂O₂
• 分子量: 459.426
• InChiKey: AXCMZPDZRTTXBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(N-(4-bromobiphenyl-3-yl)propionamido)-N-tert-butyl-3-methylbutanamide 在 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 2.0h， 以47%的产率得到N-tert-butyl-2-(3-methyl-2-oxo-6-phenylindolin-1-yl)-3-methylbutanamide
  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
• 作为产物：
  描述：

  异氰酸叔丁酯 、 4-bromo-biphenyl-3-ylamine 、 丙酸 、 异丁醛 以 甲醇 为溶剂， 反应 48.75h， 以54%的产率得到2-(N-(4-bromobiphenyl-3-yl)propionamido)-N-tert-butyl-3-methylbutanamide
  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).