N-cinnamyl-2,4-dimethylaniline

• 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-cinnamyl-2,4-dimethylaniline
• 英文别名: 2,4-dimethyl-N-[(E)-3-phenylprop-2-enyl]aniline
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: QVTVHHHXPWPYHE-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯基-1-丙炔 、 2,4-二甲基苯胺 在 四(三苯基膦)钯 、 苯甲酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以91%的产率得到N-cinnamyl-2,4-dimethylaniline
  参考文献：
  名称：

  A Convenient and Efficient Route for the Allylation of Aromatic Amines and α-Aryl Aldehydes with Alkynes in the Presence of a Pd(0)/PhCOOH Combined Catalyst System

  摘要：

  The allylation of aromatic amines with alkynes proceeded smoothly in the presence of catalytic amounts of Pd(PPh3)(4) and benzoic acid. The allylation products were obtained in high yields in a regio- and stereoselective manner. The effect of various groups on the nitrogen atom of anilines was studied. Regardless of the substituent (electron withdrawing or electron donating) on the aromatic ring, the reaction proceeded well. Various functionalities, including -CH3, -OMe, -Cl, -CN, -COOMe, -NO2 and -COCH3 were tolerated under the reaction conditions. Similarly, the allylation of alpha-aryl aldehydes proceeded well with the same level of regio- and stereoselectivity as the allylation of aromatic amines. This reaction provides the second example of the transition metal catalyzed direct alpha-allylation of aldehydes.

  DOI：

  10.1021/jo0485684

文献信息

• Direct palladium/carboxylic acid-catalyzed allylation of anilines with allylic alcohols in water
  作者：Shyh-Chyun Yang、Yi-Chun Hsu、Kim-Hong Gan

  DOI：10.1016/j.tet.2006.02.035

  日期：2006.4

  The direct activation of C-O bonds in allylic alcohols in water as a suspension medium by palladium complexes has been accelerated by carrying out the reactions in the presence of a carboxylic acid. The palladium-catalyzed allylation of anilines using allylic alcohols directly gave allylic anilines in good yields. (c) 2006 Elsevier Ltd. All rights reserved.
• A Convenient and Efficient Route for the Allylation of Aromatic Amines and α-Aryl Aldehydes with Alkynes in the Presence of a Pd(0)/PhCOOH Combined Catalyst System
  作者：Nitin T. Patil、Huanyou Wu、Isao Kadota、Yoshinori Yamamoto

  DOI：10.1021/jo0485684

  日期：2004.12.1

  The allylation of aromatic amines with alkynes proceeded smoothly in the presence of catalytic amounts of Pd(PPh3)(4) and benzoic acid. The allylation products were obtained in high yields in a regio- and stereoselective manner. The effect of various groups on the nitrogen atom of anilines was studied. Regardless of the substituent (electron withdrawing or electron donating) on the aromatic ring, the reaction proceeded well. Various functionalities, including -CH3, -OMe, -Cl, -CN, -COOMe, -NO2 and -COCH3 were tolerated under the reaction conditions. Similarly, the allylation of alpha-aryl aldehydes proceeded well with the same level of regio- and stereoselectivity as the allylation of aromatic amines. This reaction provides the second example of the transition metal catalyzed direct alpha-allylation of aldehydes.