N-allyl-N-benzyl-4-methoxybenzenamine | 150596-76-2

• 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-allyl-N-benzyl-4-methoxybenzenamine
• 英文别名: N-Allyl-N-benzyl-4-methoxyaniline；N-benzyl-4-methoxy-N-prop-2-enylaniline
• CAS: 150596-76-2
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: FHTAWZCAZGNGQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-allyl-N-benzyl-4-methoxybenzenamine 在 三氟化硼乙醚 作用下， 反应 4.5h， 以74%的产率得到N-Benzyl-2-allyl-4-methoxyaniline
  参考文献：
  名称：

  一种简单实用的二苯并[c，f]噻唑并[3,2-a]氮杂环庚烷化合物：新型熔融四环氮杂环庚烷系统

  摘要：

  从容易获得的取代的N-烯丙基-N-苄基苯胺开始，采用四步方案成功合成了一组新的功能化的二苯并[ c，f ]噻唑并[3,2- a ]氮杂s。标题化合物的合成是通过吗啡啶与巯基乙酸的环缩合完成的。通过在二氯甲烷中用氯铬酸吡啶鎓选择性氧化二氢吗啡啶来制备吗啡啶。通过酸催化取代的2-烯丙基-N-苄基苯胺的分子内Friedel-Crafts烷基化反应获得二氢吗啡啶，后者又由N-烯丙基-制备N-苄基苯胺通过芳香氨基-克莱森重排。还报告了通过高分辨率NMR对所有合成化合物的结构解析。 氨基克莱森重排-分子内Friedel-Crafts烷基化-2-烯丙基-N-苄基苯胺-二氢吗啡啶-二苯并[ c，f ]噻唑并[3,2- a ]氮杂

  DOI：

  10.1055/s-0029-1218674
• 作为产物：
  描述：

  N-烯丙基-P-甲氧基苯胺 、 氯化苄 在 silica gel 作用下， 反应 6.0h， 以85%的产率得到N-allyl-N-benzyl-4-methoxybenzenamine
  参考文献：
  名称：

  Highly selective N-Alkylation of amines promoted on silica: An efficient and recyclable surface

  摘要：

  胺类的N-烷基化面临竞争性过烷基化的问题。同时，强碱和其他苛刻条件的使用大大限制了提供实际、普遍和选择性的程序。研究发现活化硅胶能够促进胺类的N-烷基化。在此，我们研究了与各种烷基卤化物作用的胺类N-烷基化，最终构建了在环境温度下、具有可再生硅胶的单烷基或双烷基化胺的实用、高选择性和环保条件。

  DOI：

  10.1039/b905878h

文献信息

• Lewis acid-promoted 3-aza-Cope rearrangement of N-alkyl-N-allylanilines
  作者：Lars G. Beholz、John R. Stille

  DOI：10.1021/jo00071a018

  日期：1993.9

  The 3-aza-Cope rearrangement of N-alkyl-N-allylaniline substrates, which required 250-degrees-C to proceed thermally, was promoted by Lewis acid reagents at 111-140-degrees-C. Systematic studies of this reaction were performed to examine a number of reaction variables such as concentration, the stoichiometry of the Lewis acid with the substrate, the optimum temperature for rearrangement, and the type of Lewis acid reagent. Of the many Lewis acids investigated, ZnCl2 (140-degrees-C) and Et2O.BF3 (111-degrees-C) were the most generally successful reagents for promoting the aromatic 3-aza-Cope rearrangement. With respect to substrate variation, the presence of a methoxy substituent para to the N-allyl group slowed the reaction slightly, while a meta substituent accelerated the rate of [3,3] rearrangement and produced moderate site selectivity on the aromatic ring. Lewis acid-promoted rearrangement of an unsymmetrically substituted allyl moiety resulted in [3,3] sigmatropic rearrangement to give the 1-hexen-3-yl substituent on the aromatic ring. Overall, both ZnCl2 and Et2O.BF3 were shown to efficiently accelerate the regiospecific 3-aza-Cope rearrangement of N-alkyl-N-allylanilines for the purpose of forming a carbon-carbon bond between a secondary alkyl substituent and an aromatic ring.
• FeCl₃-Catalyzed Oxidative Allylation of sp² and sp³ C−H Bond Adjacent to a Nitrogen Atom: Easy Access to Homoallyl Tertiary Amines
  作者：Gullapalli Kumaraswamy、Akula Narayana Murthy、Arigala Pitchaiah

  DOI：10.1021/jo1005813

  日期：2010.6.4

  Oxidative allylation to sp(2)- and sp(3)-carbon attached to the nitrogen atom was accomplished. The alpha-allylation of tertiary amines was catalyzed by easily available hydrated iron(III) chloride in combination with air or aqueous (BuOOH)-Bu-t. Remarkably, N-allyl- and N-propagyl-tethered tertiary amines were also allylated through this protocol.
• Microwave-assisted aza-Cope rearrangement of N-allylanilines
  作者：Israel González、Iria Bellas、Ana Souto、Ramón Rodríguez、Jacobo Cruces

  DOI：10.1016/j.tetlet.2008.01.078

  日期：2008.3

  The aza-Cope rearrangement of N-allylanilines is described. The use of BF3 center dot OEt2 and microwave irradiation allows to run the transformation under mild conditions and in reaction times of minutes. (c) 2008 Published by Elsevier Ltd.