2-(2-bromobenzyl)-N,N'-bis(4-methoxybenzyl)-2-methylmalonamide | 1174193-14-6

• 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-(2-bromobenzyl)-N,N'-bis(4-methoxybenzyl)-2-methylmalonamide
• 英文别名: 2-[(2-bromophenyl)methyl]-N,N'-bis[(4-methoxyphenyl)methyl]-2-methylpropanediamide
• CAS: 1174193-14-6
• 化学式: C₂₇H₂₉BrN₂O₄
• 分子量: 525.442
• InChiKey: RAODRCHCYJPRLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-bromobenzyl)-N,N'-bis(4-methoxybenzyl)-2-methylmalonamide 在 (R)-MOP 、 palladium diacetate 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (S)-3-methyl-N,1-bis(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxamide 、 (R)-3-methyl-N,1-bis(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxamide
  参考文献：
  名称：

  Desymmetrization of malonamides via an enantioselective intramolecular Buchwald–Hartwig reaction

  摘要：

  A new form of enantioselective nitrogen arylation reaction is described. Beginning with symmetrical alpha-(2-bromobenzyl)malonamides, intramolecular palladium-catalyzed cross-coupling using a catalyst system including 3.3 mol % Pd(OAc)(2) and 6.6 mol % of the chiral biaryl monophosphine (R)-MOP, desymmetrized quinolinone products are obtained in nearly quantitative yields in enantiomeric ratios up to 88:12. This Letter represents a rare example of enantioselective Buchwald-Hartwig reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.133
• 作为产物：
  描述：

  、 4-甲氧基苄胺 在 三乙胺 作用下， 以 氯仿 为溶剂， 以760 mg的产率得到2-(2-bromobenzyl)-N,N'-bis(4-methoxybenzyl)-2-methylmalonamide
  参考文献：
  名称：

  Desymmetrization of malonamides via an enantioselective intramolecular Buchwald–Hartwig reaction

  摘要：

  A new form of enantioselective nitrogen arylation reaction is described. Beginning with symmetrical alpha-(2-bromobenzyl)malonamides, intramolecular palladium-catalyzed cross-coupling using a catalyst system including 3.3 mol % Pd(OAc)(2) and 6.6 mol % of the chiral biaryl monophosphine (R)-MOP, desymmetrized quinolinone products are obtained in nearly quantitative yields in enantiomeric ratios up to 88:12. This Letter represents a rare example of enantioselective Buchwald-Hartwig reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.133