4-(2-(4-methoxyphenyl)propyl)morpholine | 1440521-83-4

• 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: 4-(2-(4-methoxyphenyl)propyl)morpholine
• 英文别名: 4-[2-(4-Methoxyphenyl)propyl]morpholine
• CAS: 1440521-83-4
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: MJVIZETUFXMCBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  茴香烯 在 methoxy(cyclooctadiene)rhodium(I) dimer 、 抗氧剂168 、 氢气 、 M₇₃SIPr 作用下， 以 甲苯 为溶剂， 60.0~120.0 ℃ 、6.0 MPa 条件下， 反应 26.0h， 生成 4-(2-(4-methoxyphenyl)propyl)morpholine
  参考文献：
  名称：

  2‐Arylpropylamines from 1‐Propenylbenzenes in a New One‐Pot Metathesis–Hydroaminomethylation Protocol

  摘要：

  Abstract2‐Arylpropylamines are useful as active pharmaceutical ingredients (APIs) and as synthetic building blocks in fine chemistry. Herein we report a new and efficient methodology to transform naturally occurring 1‐propenylbenzenes into 2‐arylpropylamines employing a one‐pot ethenolysis/hydroaminomethylation protocol. Four consecutive reactions must occur in the same reaction vessel and the careful selection of the reaction conditions was critical to obtain the desired products in high yields. The negative interference between the ethenolysis and the hydroaminomethylation (HAM) catalysts was circumvented by the appropriate adjustment on the molar ratio of the catalysts. As a result, nine 2‐arylpropylamines were obtained in yields ranging in 75–93 %.

  DOI：

  10.1002/cctc.202201186

文献信息

• Glycerol Boosted Rh‐Catalyzed Hydroaminomethylation Reaction: A Mechanistic Insight
  作者：Alejandro Serrano‐Maldonado、Trung Dang‐Bao、Isabelle Favier、Itzel Guerrero‐Ríos、Daniel Pla、Montserrat Gómez

  DOI：10.1002/chem.202001978

  日期：2020.10

  We report a Rh‐catalyzed hydroaminomethylation reaction of terminal alkenes in glycerol that proceeds efficiently under mild conditions to produce the corresponding amines in relatively high selectivity towards linear amines, moderate to excellent yields by using a low catalyst loading (1 mol % [Rh], 2 mol % phosphine) and relative low pressure (H2/CO, 1:1, total pressure 10 bar). This work sheds light

  我们报道了甘油中末端烯烃的Rh催化加氢氨基甲基化反应，该反应在温和条件下有效地进行，以相对高的线性胺选择性生成相应的胺，通过使用低催化剂负载量（1 mol％[Rh]， 2摩尔％的膦）和相对低压（H 2/ CO，1：1，总压力10 bar）。这项工作揭示了甘油在通过氢转移使烯胺还原中的重要性。而且，通过排除有害的醛醇缩合反应，首次在加氢氨基甲基化反应的框架中获得了Rh在缩合步骤中作为化学选择性催化剂的关键作用的证据。氢氨基甲基化是在分子机制下进行的。催化活性物质进入金属基纳米颗粒的结果使催化体系失去活性。
• Homogeneous and Semi-Heterogeneous Magnetically Retrievable Bis-N-Heterocyclic Carbene Rhodium(I) Based Catalysts for Selective Hydroaminomethylation Reactions
  作者：Bishnu Dutta、Rony Schwarz、Suheir Omar、Suzana Natour、Raed Abu-Reziq

  DOI：10.1002/ejoc.201403526

  日期：2015.3

  reactivity and selectivity compared to catalysts containing bidentate phosphine or monodentate NHC ligands. A triethoxysilyl-functionalized bis-NHC ligand was immobilized on magnetic nanoparticles and then utilized to bind a rhodium catalyst. The resulting catalytic system was successfully employed in hydroaminomethylation reactions. The catalyst exhibited excellent reactivity, high selectivity, and was

  研究了铑的各种双-N-杂环卡宾（双-NHC）配合物的制备及其在乙烯基芳烃氢氨甲基化中的应用。测试了各种反应参数，如溶剂、温度和压力，并将优化的方案应用于各种乙烯基芳烃和胺，以良好的收率和对支化产物的高选择性提供相应的胺。与含有双齿膦或单齿 NHC 配体的催化剂相比，基于双 NHC 的催化剂表现出优异的反应性和选择性。三乙氧基甲硅烷基官能化的双 NHC 配体固定在磁性纳米粒子上，然后用于结合铑催化剂。所得催化体系成功用于加氢氨甲基化反应。
• Rhodium-Catalyzed Highly Regioselective Hydroaminomethylation of Styrenes with Tetraphosphorus Ligands
  作者：Shengkun Li、Kexuan Huang、Jiwen Zhang、Wenjun Wu、Xumu Zhang

  DOI：10.1021/ol4012635

  日期：2013.6.21

  The highly linear-selective hydroaminomethylation of styrenes is very challenging. Herein, an efficient, highly chemoselective, and linear-selective hydroaminomethylation (l/b up to >99:1) of styrenes using Rh(nbd)2SbF6 with a pyrrole-based 3,3′,5,5′-substituted tetraphosphorus ligand is documented. This is in sharp contrast to other available processes leading to branched amines and provides a novel

  苯乙烯的高度线性选择性的氢氨基甲基化是非常具有挑战性的。本文中，使用具有吡咯基3,3'，5,5'-取代的Rh（nbd）2 SbF 6的苯乙烯高效，高度化学选择性和线性选择性氢氨基甲基化（l / b高达> 99：1）记录了四磷配体。这与导致支链胺的其他可用方法形成鲜明对比，并为3-芳基丙胺提供了一种新颖的原子经济方法。