N-(3-(p-tolyl)propyl)aniline | 1739-14-6

• 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-(3-(p-tolyl)propyl)aniline
• 英文别名: N-[3-(4-methylphenyl)propyl]aniline
• CAS: 1739-14-6
• 化学式: C₁₆H₁₉N
• 分子量: 225.334
• InChiKey: YWHKWPNZMCOLNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-苯甲酰替苯胺 在 苯硅烷 、 C₁₉H₂₆ClIrN₃⁽¹⁺⁾*Cl^(1-) 作用下， 以 对二甲苯 为溶剂， 反应 24.0h， 生成 N-(3-(p-tolyl)propyl)aniline
  参考文献：
  名称：

  铱催化的羧酸还原胺化

  摘要：

  我们的 Ir 催化的羧酸与胺的还原胺化反应产生结构多样的N-烷基化胺，收率非常好（多达 60 个例子）。该协议具有条件温和、操作方便、功能容错性好等优点。通过合成两种药物分子——Cinacalcet 和 ( R )-Fendiline，突出了合成价值。

  DOI：

  10.1016/j.jcat.2023.01.030

文献信息

• A 2,6-Bis(phenylamino)pyridinato Titanium Catalyst for the Highly Regioselective Hydroaminoalkylation of Styrenes and 1,3-Butadienes
  作者：Jaika Dörfler、Till Preuß、Alexandra Schischko、Marc Schmidtmann、Sven Doye

  DOI：10.1002/anie.201403203

  日期：2014.7.21

  hydroaminoalkylation of terminal alkenes, 1,3‐dienes, or styrenes allows a direct and highly atom efficient (100 %) synthesis of amines which can result in the formation of two regioisomers, the linear and the branched product. We present a new titanium catalyst with 2,6‐bis(phenylamino)pyridinato ligands for intermolecular hydroaminoalkylation reactions of styrenes and 1‐phenyl‐1,3‐butadienes that delivers the

  与c  C键的形成末端烯烃，1,3-二烯，或苯乙烯的催化hydroaminoalkylation允许胺的直接和高度原子效率的（100％）的合成可导致形成两种区域异构体的，直链和支链产物。我们提出了一种新型的带有2,6-双（苯基氨基）吡啶基配体的钛催化剂，用于苯乙烯和1-苯基-1,3-丁二烯的分子间加氢烷基化反应，可提供相应的线性加氢烷基化产物，具有出色的区域选择性。
• Heterogeneous Ru/TiO₂ for hydroaminomethylation of olefins: multicomponent synthesis of amines
  作者：Jinghua An、Zhuyan Gao、Yehong Wang、Zhixin Zhang、Jian Zhang、Lu Li、Bo Tang、Feng Wang

  DOI：10.1039/d1gc00113b

  日期：——

  Synthesizing amines via the hydroaminomethylation (HAM) reaction of olefins, a multicomponent reaction, has been regarded as one of the most attractive methods compared with the traditional methods considering the atom economy and environmental friendliness. However, the use of homogeneous catalysts, complex ligands containing diphosphine or nitrogen, and base or acid additives has severely hampered

  合成胺通过烯烃，多组分反应的hydroAMinomethylation（HAM）反应，被认为是与考虑到原子经济性和环境友好性的传统方法相比，最有吸引力的方法之一。然而，均相催化剂，含有二膦或氮的复杂配体以及碱或酸添加剂的使用严重地阻碍了这些方法的使用。在本文中，开发了没有任何添加剂的有效的异质Ru / TiO 2催化的烯烃HAM反应。可以从包括芳族和脂族烯烃在内的烯烃中成功地获得包括仲胺和叔胺在内的各种胺。系统研究表明，Ruδ +的电子密度较低Ru / TiO 2的酸位较高，导致烯烃的高HAM反应活性。最重要的是，硝基苯衍生物也可以优良的产率通过Ru / TiO 2转化为相应的产物。
• Fast Titanium‐Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine
  作者：Jens Bielefeld、Sven Doye

  DOI：10.1002/anie.202001111

  日期：2020.4.6

  The scientific interest in catalytic hydroaminoalkylation reactions of alkenes has vastly increased over the past decade, but these reactions have struggled to become a viable option for general laboratory or industrial use because of reaction times of several days. The titanium-based catalytic system introduced in this work not only reduces the reaction time by several orders of magnitude, into the

  在过去的十年中，人们对烯烃催化加氢氨基烷基化反应的科学兴趣大大增加，但由于反应时间长达数天，这些反应一直难以成为一般实验室或工业用途的可行选择。这项工作中引入的钛基催化系统不仅将反应时间缩短了几个数量级，达到几分钟的范围，而且该催化剂也被证明可以很容易地从普通起始材料中获得，成本约为 1 欧元每毫摩尔催化剂。我们还能够正式对甲胺进行 CH 活化，并通过胺的甲硅烷基保护和简单的水脱保护实现与多种烯烃的偶联。
• [Ind₂TiMe₂]: A Catalyst for the Hydroaminomethylation of Alkenes and Styrenes
  作者：Raphael Kubiak、Insa Prochnow、Sven Doye

  DOI：10.1002/anie.200906557

  日期：2010.3.29

  Metal‐catalyzed hydroaminomethylations of styrenes, which take place by CH bond activation, can be achieved in the presence of the catalyst [Ind2TiMe2] (Ind=η5‐indenyl). Corresponding reactions of 1‐alkenes with N‐methylanilines performed at temperatures between 80 °C and 105 °C usually take place with regioselectivities of better than 99:1 in favor of the branched product.

  金属催化hydroaminomethylations苯乙烯的，其被C发生 H键活化，可以在催化剂的存在下[工业可实现2时间2 ]（茚=η 5 -茚基）。1-烯烃与N-甲基苯胺的相应反应通常在80°C至105°C之间进行，区域选择性优于99：1，有利于支链产物。
• Regioselective Hydroaminomethylation of Vinylarenes by a Sol–Gel Immobilized Rhodium Catalyst
  作者：Zackaria Nairoukh、Jochanan Blum

  DOI：10.1021/jo402632s

  日期：2014.3.21

  In the course of our studies toward the development of new heterogeneous conditions for better controlling regioselectivity in organic reactions, we investigated the application of sol-gel immobilized organometallic catalyst for regioselective hydroaminomethylation of vinylarenes with aniline or nitroarene derivatives in an aqueous microemulsion. By immobilization of 6 mol % [Rh(cod)Cl]2 within a hydrophobic silica sol-gel matrix we were able to perform efficient hydroaminomethylation under mild conditions and isolate 2-arylpropylamines with high regioselectivity. The regioselectivity of the reaction was found to be mainly dependent on the hydrophobicity of the catalyst support. It is also significantly affected by the electronic nature of the substrates, by the reaction temperature, and by syngas pressure. The heterogenized catalyst can be reused for several times.