N-(3,5-dimethoxybenzyl)aniline | 625407-59-2

• 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-(3,5-dimethoxybenzyl)aniline
• 英文别名: N-[(3,5-dimethoxyphenyl)methyl]aniline
• CAS: 625407-59-2
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: BCDMYZJLMDIQNR-UHFFFAOYSA-N

物化性质

• 沸点：
  391.4±27.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  烯丙基三甲氧基硅烷 、 N-(3,5-dimethoxybenzyl)aniline 在 silver trifluoromethanesulfonate 、 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三氟甲磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 15.33h， 以88%的产率得到N-[1-(3,5-dimethoxyphenyl)-3-butenyl]-N-phenylamine
  参考文献：
  名称：

  A silver triflate-catalyzed cascade of in situ-oxidation and allylation of arylbenzylamines

  摘要：

  A silver-triflate catalyzed cascade of in situ-oxidation and allylation of arylbenzylamines is reported. The 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate is employed as a mild oxidant which is compatible with both catalyst and ligand. Racemic BINAP is also utilized to assist with the catalyst in regulating the yields of products. Various homoallylic amines are obtained in 39-99% yields. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.06.076
• 作为产物：
  描述：

  在 水 作用下， 生成 N-(3,5-dimethoxybenzyl)aniline
  参考文献：
  名称：

  芳香族和脂肪族硝基化合物与有机卤化物的无催化剂还原偶联

  摘要：

  已经实现了硝基化合物与有机卤化物的罕见还原偶联。该反应通过将硝基部分还原为亚硝基中间体而引发。因此，不仅芳香族而且硝基脂肪族化合物也有效地转化为单烷基化的胺，并用有机卤化物作为烷基化剂。考虑到亚硝基化合物的先天反应性，不需要催化剂，导致对两种起始原料中的芳基卤化物取代基具有较高的耐受性。

  DOI：

  10.1002/anie.201814197

文献信息

• Mimicking transition metals in borrowing hydrogen from alcohols
  作者：Ananya Banik、Jasimuddin Ahmed、Swagata Sil、Swadhin K. Mandal

  DOI：10.1039/d1sc01681d

  日期：——

  Borrowing hydrogen from alcohols, storing it on a catalyst and subsequent transfer of the hydrogen from the catalyst to an in situ generated imine is the hallmark of a transition metal mediated catalytic N-alkylation of amines. However, such a borrowing hydrogen mechanism with a transition metal free catalytic system which stores hydrogen molecules in the catalyst backbone is yet to be established

  从醇中借用氢气，将其储存在催化剂上，然后将氢气从催化剂转移到原位生成的亚胺，这是过渡金属介导的胺催化N-烷基化的标志。然而，这种在催化剂主链中储存氢分子的无过渡金属催化系统的借氢机制尚未建立。在此，我们证明苯酚基配体可以模仿过渡金属在储存和转移氢分子中的作用，从而导致借氢介导的醇类苯胺烷基化，包括广泛的底物范围。通过各种光谱技术、氘标记实验和 DFT 研究表征几种中间体，对机制途径进行了仔细检查，得出的结论是，基于苯酚基的主链通过脱芳构化过程依次添加 H + 、 H˙ 和一个电子，随后将其用作还原剂。相当于催化方式中的C-N双键。
• ROMP-Boranes as Moisture-Tolerant and Recyclable Lewis Acid Organocatalysts
  作者：Fernando Vidal、James McQuade、Roger Lalancette、Frieder Jäkle

  DOI：10.1021/jacs.0c05454

  日期：2020.8.26

  linear copolymer and a cross-linked organogel. The polymers proved highly efficient as recyclable catalysts in the reductive N-alkylation of arylamines under mild conditions and at exceptionally low catalyst loadings. The modular design presented herein can be readily adapted to other finely tuned triarylboranes, enabling wide applications of ROMP-borane polymers as well-defined supported organocatalysts

  尽管广泛用于催化，但通常采用的多步合成和高负载限制了高活性定制芳基硼烷路易斯酸和路易斯对的更广泛实施。迄今为止，开发可回收系统的尝试取得了有限的成功，因为尚未开发出通用的多功能平台。我们展示了一种基于开环复分解聚合 (ROMP) 的出色控制和官能团耐受性的新方法。高度路易斯酸性硼烷官能化苯基降冰片烯的 ROMP 可提供可溶性线性共聚物和交联有机凝胶。在温和条件下和极低的催化剂负载量下，该聚合物被证明作为芳胺还原性 N-烷基化反应中的可回收催化剂非常有效。
• Cobalt–Rhodium Heterobimetallic Nanoparticle-Catalyzed N-Alkylation of Amines with Alcohols to Secondary and Tertiary Amines
  作者：Hyunho Chung、Young Keun Chung

  DOI：10.1021/acs.joc.8b01109

  日期：2018.8.3

  selectively catalyze both mono- and bis-N-alkylation through the coupling of simple alcohols with amines, yielding a range of secondary and tertiary amines in good to excellent isolated yields. The reaction can be applied to benzyl alcohol with optically active 1-phenylethan-1-amines, and secondary amines were isolated in quantitative yields with an excellent enantiomeric excess (ee > 94%). Selectivity

  不需要碱或其他添加剂，Co 2 Rh 2 / C可以通过简单的醇与胺的偶联选择性催化单-和双-N-烷基化，生成一系列仲胺和叔胺，分离收率好至极好。该反应可与具有光学活性的1-苯基乙-1-胺一起用于苄醇，并以定量收率分离仲胺，其对映体过量极佳（ee> 94％）。通过改变反应温度和所用催化剂的量来实现选择性。该催化体系具有许多优点，包括环保和简单的后处理程序。催化剂可以成功回收并重复使用十次，而活性没有任何重大损失。
• Polymeric Bimetallic Catalyst-Promoted In-Water Dehydrative Alkylation of Ammonia and Amines with Alcohols
  作者：Yoichi Yamada、Yasuhiro Uozumi、Hidetoshi Ohta、Yoshinari Yuyama

  DOI：10.1055/s-0033-1338797

  日期：——

  A dehydrative alkylation with three kinds of Ir/B heterobimetallic polymeric catalysts in water is reported. The polymeric heterobimetallic catalysts were readily prepared by ionic convolution of a poly(catechol borate) and iridium complexes. The N-alkylation of ammonia and amines with alcohols, as alkylating agents, was carried out with a heterogeneous catalyst (1 mol% Ir) at 100 degrees C without the use of organic solvents under aerobic and aqueous conditions to afford the corresponding alkylated amines in high yield.
• In-Water Dehydrative Alkylation of Ammonia and Amines with Alcohols by a Polymeric Bimetallic Catalyst
  作者：Hidetoshi Ohta、Yoshinari Yuyama、Yasuhiro Uozumi、Yoichi M. A. Yamada

  DOI：10.1021/ol201422s

  日期：2011.8.5

  An in-water dehydrative alkylation with a novel heteroblmetallic polymeric catalyst Is described. Thus, a boron iridium heteroblmetallic polymeric catalyst was prepared by ionic convolution of a poly(catechol borate) and an Iridium complex. The alkylation of ammonia and amines with alcohols, alkylating agents, was performed with 1 mol % Ir of the heterogeneous catalyst In water without the use of organic solvents under aerobic conditions to give the corresponding alkylated amines.