N-allyl-N-(but-3-enyl)-4-methoxybenzenamine | 443754-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-allyl-N-(but-3-enyl)-4-methoxybenzenamine
• 英文别名: N-but-3-enyl-4-methoxy-N-prop-2-enylaniline
• CAS: 443754-68-5
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: IKHQFROHBLSDTR-UHFFFAOYSA-N

物化性质

• 沸点：
  322.9±42.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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-(but-3-enyl)-4-methoxybenzenamine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到1-(4-甲氧基苯基)-3,6-二氢-2H-吡啶
  参考文献：
  名称：

  FeCl₃-Catalyzed Oxidative Allylation of sp² and sp³ C−H Bond Adjacent to a Nitrogen Atom: Easy Access to Homoallyl Tertiary Amines

  摘要：

  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.

  DOI：

  10.1021/jo1005813
• 作为产物：
  描述：

  N-allyl-4-methoxy-N-methylaniline 、 烯丙基三丁基锡 在 叔丁基过氧化氢 、 iron(III) chloride hexahydrate 作用下， 以 水 、 乙腈 为溶剂， 以65%的产率得到N-allyl-N-(but-3-enyl)-4-methoxybenzenamine
  参考文献：
  名称：

  FeCl₃-Catalyzed Oxidative Allylation of sp² and sp³ C−H Bond Adjacent to a Nitrogen Atom: Easy Access to Homoallyl Tertiary Amines

  摘要：

  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.

  DOI：

  10.1021/jo1005813

文献信息

• Synthesis of medium-sized aryl-fused nitrogenous heterocycles <i>via</i> sequential aryne aza-Claisen rearrangement/ring-closing metathesis
  作者：N. S. V. M. Rao Mangina、Ravinder Guduru、Galla V. Karunakar

  DOI：10.1039/c7ob03166a

  日期：——

  The reaction of arynes and secondary allylamines furnished ortho-allyl-substituted N-arylanilines via an aza-Claisen rearrangement. In this transformation, the sequential formation of C–C and C–N bonds occurred by involving two aryne molecules under metal-free reaction conditions to provide moderate to good yields of the products. The obtained ortho-allyl-substituted N-arylaniline derivatives were

  芳烃和仲烯丙胺的反应通过氮杂-克莱森重排提供邻-烯丙基取代的N-芳基苯胺。在这种转化过程中，通过在无金属反应条件下使两个芳烃分子参与进来，从而形成了C–C和C–N键的顺序形成，从而提供了中等至良好的收率。获得的邻烯丙基取代的N-芳基苯胺衍生物通过闭环复分解（RCM）进一步转化为芳基稠合的中等大小（7-9）含氮杂环分子，例如氮杂，氮杂和苯丙氨酸。