N-allyl-3,5-dimethoxyaniline

• 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-3,5-dimethoxyaniline
• 英文别名: 3,5-dimethoxy-N-prop-2-enylaniline
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: ZMLNZALPWDUGGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对苯醌 、 N-allyl-3,5-dimethoxyaniline 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以72%的产率得到9-allyl-5,7-dimethoxy-9H-carbazol-3-ol
  参考文献：
  名称：

  通过富电子苯胺和醌的单步合成3-羟基咔唑

  摘要：

  在室温下，通过在PhMe / AcOH（4：1）中富电子苯胺和醌的环化反应，可以一步合成3-羟基咔唑。这种化学方法可以耐受各种取代的苯醌和萘醌，但是对苯胺的电子和空间特性均敏感。所需的3-羟基咔唑衍生物通常以中等收率生产。

  DOI：

  10.1016/j.tetlet.2016.11.009
• 作为产物：
  描述：

  烯丙醇 、 3,5-二甲氧基苯胺 在 palladium diacetate 、 三苯基膦 titanium(IV) isopropylate 、 MS 4 Angstroem 作用下， 以 苯 为溶剂， 反应 3.0h， 以98%的产率得到N-allyl-3,5-dimethoxyaniline
  参考文献：
  名称：

  Direct palladium-catalyzed selective monoallylation of anilines using allylic alcohols

  摘要：

  N-Allylation of anilines using allylic alcohols directly to give monoallylic anilines selectively in high yields has been realized by employing palladium acetate-triphenylphosphine as the catalyst. Palladium-catalyzed one-pot cyclization of 2-aminophenols with 2-butene-1,4-diol leads to 3,4-dihydro-2-vinyl-2H-1,4-benzoxazines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01171-0

文献信息

• Sequential Allylic Substitution/Pauson–Khand Reaction: A Strategy to Bicyclic Fused Cyclopentenones from MBH-Acetates of Acetylenic Aldehydes
  作者：Chada Raji Reddy、Paridala Kumaraswamy、Kiran K. Singarapu

  DOI：10.1021/jo500962d

  日期：2014.9.5

  approach for the construction of novel bicyclic fused cyclopentenones starting from Morita–Baylis–Hillman (MBH) acetates of acetylenic aldehydes with flexible scaffold diversity has been achieved using a two-step reaction sequence involving allylic substitution and the Pauson–Khand reaction. This strategy provided a facile access to various bicyclic cyclopentenones fused with either a carbocyclic or a

  使用包含烯丙基取代和Pauson-Khand反应的两步反应序列，已成功构建了一种新的双环稠合环戊烯酮（从具有柔性骨架多样性的炔属乙醛的Morita-Baylis-Hillman（MBH）乙酸酯开始）的构建方法。该策略提供了以良好收率容易地获得与碳环或杂环系统稠合的各种双环环戊烯酮的途径。
• Palladium-catalyzed N-allylation of anilines by direct use of allyl alcohols in the presence of titanium(IV) isopropoxide
  作者：Shyh-Chyun Yang、Wen-Hung Chung

  DOI：10.1016/s0040-4039(98)02456-3

  日期：1999.1

  The direct activation of C-O bonds in allyl alcohols by palladium complexes has been accelerated by carrying out the reactions in the presence of titanium(IV) isopropoxide and 4A molecular sieves. N-Allylation of anilines to give mono- and diallylanilines using allyl alcohols directly has been realized by employing palladium catalysts. (C) 1999 Elsevier Science Ltd. All rights reserved.
• An Efficient Palladium-Catalyzed Route to N-Allylanilines by the Direct Use of Allyl Alcohols
  作者：Shyh-Chyun Yang

  DOI：10.1055/s-1999-3584

  日期：1999.10
• Direct palladium-catalyzed selective monoallylation of anilines using allylic alcohols
  作者：Shyh-Chyun Yang、Chia-Lin Yu、Yan-Chiu Tsai

  DOI：10.1016/s0040-4039(00)01171-0

  日期：2000.9

  N-Allylation of anilines using allylic alcohols directly to give monoallylic anilines selectively in high yields has been realized by employing palladium acetate-triphenylphosphine as the catalyst. Palladium-catalyzed one-pot cyclization of 2-aminophenols with 2-butene-1,4-diol leads to 3,4-dihydro-2-vinyl-2H-1,4-benzoxazines. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Single-step synthesis of 3-hydroxycarbazoles by annulation of electron-rich anilines and quinones
  作者：Eugenia Pushkarskaya、Brian Wong、Chong Han、Simona Capomolla、Chunang Gu、Brian M. Stoltz、Haiming Zhang

  DOI：10.1016/j.tetlet.2016.11.009

  日期：2016.12

  A single-step synthesis of 3-hydroxycarbazoles has been achieved via annulation of electron-rich anilines and quinones in PhMe/AcOH (4:1) at room temperature. This chemistry tolerates various substituted benzoquinones and naphthoquinones, however, is sensitive to both the electronic and steric properties of the anilines. The desired 3-hydroxycarbazole derivatives are generally produced in moderate

  在室温下，通过在PhMe / AcOH（4：1）中富电子苯胺和醌的环化反应，可以一步合成3-羟基咔唑。这种化学方法可以耐受各种取代的苯醌和萘醌，但是对苯胺的电子和空间特性均敏感。所需的3-羟基咔唑衍生物通常以中等收率生产。