N,N'-(phenylmethylene)bis(2-methylpropanamide) | 17102-76-0

• 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: N,N'-(phenylmethylene)bis(2-methylpropanamide)
• 英文别名: 2-methyl-N-[(2-methylpropanoylamino)-phenylmethyl]propanamide
• CAS: 17102-76-0
• 化学式: C₁₅H₂₂N₂O₂
• 分子量: 262.352
• InChiKey: FIBCIPQSUYIDMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  异丁酰胺 、 苯甲醛 在 三甲基氯硅烷 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以92%的产率得到N,N'-(phenylmethylene)bis(2-methylpropanamide)
  参考文献：
  名称：

  N,N′-(Phenylmethylene)diacetamide Analogues as Economical and Efficient Ligands in Copper-Catalyzed Arylation of Aromatic Nitrogen-Containing Heterocycles

  摘要：

  N,N′-(苯亚甲基)二乙酰胺类似物是通过醛与酰胺或尿素的缩合反应简单制备而成的，发现其在铜催化的芳基卤化物与各种杂环核苷酸的偶联反应中是有效的配体。新开发的配体在该转化过程中显示了广泛的应用范围。包括咪唑、苯并咪唑、呋喃、吲哚和苯并三唑等化合物成功地与多样化的芳香卤化物发生芳基化反应，得到相应的产物，产率中等到优秀。

  DOI：

  10.1055/s-0028-1087350

文献信息

• A convenient synthesis of bisamides with BF3 etherate as catalyst
  作者：Yi Zhang、Zhihao Zhong、Yingmei Han、Ruirui Han、Xu Cheng

  DOI：10.1016/j.tet.2013.11.017

  日期：2013.12

  A convenient synthesis of bisamide from aldehyde and amide with BF3 etherate as catalyst was reported. Both aryl and aliphatic bisamides could be prepared with this procedure in high yield at room temperature and the catalyst loading as low as 0.5 mol % was achieved. Fine-tuned solvent was utilized for both rapid conversion and simple isolation. Two CB2 receptor inverse agonists were synthesized with

  从醛和酰胺与BF双酰胺的一种方便的合成3作为报道醚合物催化剂。可以通过该方法在室温下以高收率制备芳基和脂族双酰胺，并且催化剂的负载量低至0.5 mol％。微调的溶剂可用于快速转化和简单分离。两个CB 2受体反向激动剂，用该协议以高收率合成。
• Synthesis and Preliminary Pharmacological Evaluation of a Series of N,N′-Arylidenebis(acid amides)
  作者：Theron A. Ebel、Arthur A. Harwood、Allan M. Burkman

  DOI：10.1021/jm00317a045

  日期：1967.9
• <i>N</i>,<i>N</i>′-(Phenylmethylene)diacetamide Analogues as Economical and Efficient Ligands in Copper-Catalyzed Arylation of Aromatic Nitrogen-Containing Heterocycles
  作者：Yuan-Jiang Pan、Jie-Ping Wan、Yun-Feng Chai、Jian-Mei Wu

  DOI：10.1055/s-0028-1087350

  日期：2008.12

  N,N′-(Phenylmethylene)diacetamide analogues which were simply prepared from the condensation reaction of an aldehyde with an amide or urea were found to be efficient ligands in copper-catalyzed coupling reaction of aryl halides with various azole nucleophiles. The newly developed ligand showed broad application scope in this conversion. Compounds including imidazoles, benzoimidazoles, pyrrole, indole, and benzotriazole were successfully arylated with diversified aromatic halides to give corresponding products in moderate to excellent yields.

  N,N′-(苯亚甲基)二乙酰胺类似物是通过醛与酰胺或尿素的缩合反应简单制备而成的，发现其在铜催化的芳基卤化物与各种杂环核苷酸的偶联反应中是有效的配体。新开发的配体在该转化过程中显示了广泛的应用范围。包括咪唑、苯并咪唑、呋喃、吲哚和苯并三唑等化合物成功地与多样化的芳香卤化物发生芳基化反应，得到相应的产物，产率中等到优秀。