N-(1-phenylhexa-1,5-dien-3-yl)aniline | 144661-26-7

• 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-(1-phenylhexa-1,5-dien-3-yl)aniline
• 英文别名: N-(1-phenylhexa-1,5-dien-3-yl)benzenamine；N-(1-Phenylhexa-1,5-dien-3-yl)aniline
• CAS: 144661-26-7
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: JSRIGJPIVTXRGL-UHFFFAOYSA-N

物化性质

• 沸点：
  420.4±44.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  N-(3-phenylallylidene)benzenamine 在 sodium tetrahydroborate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.0h， 生成 N-(1-phenylhexa-1,5-dien-3-yl)aniline
  参考文献：
  名称：

  DDQ促进苄基苯胺烯丙基化的交叉脱氢偶联策略

  摘要：

  报道了由DDQ促进的苄基苯胺的烯丙基化的交叉脱氢偶联策略，其在温和条件下在N-苄基苯胺的烯丙基化中使用非金属醌DDQ作为氧化剂。在该反应中构建了具有高选择性和活性的C–C键，并以高达99％的产率获得了均烯丙基胺。

  DOI：

  10.1016/j.tet.2019.130798

文献信息

• Solvent-free allylation and benzylation of aldimines mediated by zinc powder
  作者：Yumei Zhang、Tingli Yan、Wei Cheng、Jianming Zuo、Weijie Zhao

  DOI：10.1016/j.tetlet.2009.03.184

  日期：2009.6

  A rapid and efficient procedure for allylation and benzylation of aldimines mediated by zinc powder under solvent-free conditions is described. The procedure is operationally simple, higher regioselective, and gives good to excellent yields.

  描述了一种在无溶剂条件下由锌粉介导的醛胺的烯丙基化和苄基化的快速有效方法。该程序操作简单，区域选择性高，并且收率良好。
• Montmorillonite Clay-Catalyzed Three-Component Coupling Reactions: A Facile Synthesis of Homoallylic Amines
  作者：J. S. Yadav、B. V. S. Reddy、A. Krishnam Raju、D. Gnaneshwar

  DOI：10.1002/1615-4169(200210)344:9<938::aid-adsc938>3.0.co;2-z

  日期：2002.10

  Homoallylic amines are synthesized by the three-component coupling reaction of aldehydes, amines and allyltributylstannane using a heterogeneous solid acid catalyst, montmorillonite KSF, under mild reaction conditions to afford the corresponding homoallylic amines in excellent yields.

  在温和的反应条件下，使用多相固体酸催化剂蒙脱土KSF，通过醛，胺和烯丙基三丁基锡烷的三组分偶联反应，可以合成均烯丙基胺，从而以优异的收率得到相应的均烯丙基胺。
• Highly efficient synthesis of homoallylic alcohols and amines via allylation of aldehydes and imines catalyzed by ZrOCl2·8H2O in water
  作者：Wei Shen、Li-Min Wang、Jian-Jun Feng、He Tian

  DOI：10.1016/j.tetlet.2008.04.084

  日期：2008.6

  The allylation of aldehydes and imines has efficiently been carried out by treatment with allyltributylstannane in the presence of a catalytic amount of ZrOCl2·8H2O in water to form the corresponding homoallylic alcohols and amines, respectively, in high yields.

  通过在水中催化量的ZrOCl 2 ·8H 2 O的存在下，用烯丙基三丁基锡烷进行处理，可以有效地进行醛和亚胺的烯丙基化反应，从而分别高产率地形成相应的均烯丙基醇和胺。
• A Simple and Efficient Method for the Three-Component Synthesis of Homoallylic Amines Catalyzed by Indium Triflate
  作者：A. Narsaiah、J. Kumar、P. Narsimha

  DOI：10.1055/s-0029-1219762

  日期：2010.5

  Indium triflate catalyzes efficiently the one-pot three-component condensation of aldehydes, amines, and allyltributylstannane to afford the corresponding products of homoallylic amines in excellent yields at room temperature. All reactions were carried out using the catalyst in 10 mol%. This methodology was successfully applied to a variety of aldehydes and amines. aldehydes - amines - allyltributylstannane

  三氟甲磺酸铟有效地催化醛，胺和烯丙基三丁基锡烷的一锅三组分缩合反应，从而在室温下以优异的收率得到相应的均烯丙基胺产物。所有反应均使用10摩尔％的催化剂进行。该方法已成功应用于各种醛和胺。 醛-胺-烯丙基三丁基锡烷-三氟甲磺酸铟-均烯丙基胺
• A distinct approach for the rapid synthesis of homoallylic amines starting directly from nitro compounds in water
  作者：Biswanath Das、Gandham Satyalakshmi、Kanaparthy Suneel、Boddu Shashikanth

  DOI：10.1016/j.tetlet.2008.10.010

  日期：2008.12

  Three-component reactions of nitroarenes, benzaldehydes, and allyltributylstannane using indium in dilute aqueous HCl at room temperature afford the corresponding homoallylic amines in high yields within 5-10 min. The conversion in one-pot synthesis involves the following steps: (i) reduction of nitro compounds to amines, (ii) formation of imines from amines and aldehydes, and (iii) allylation of imines. (C) 2008 Elsevier Ltd. All rights reserved.