N-phenyl-m-phenoxybenzylamine

• 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-phenyl-m-phenoxybenzylamine
• 英文别名: N-(3-phenoxybenzyl)aniline；N-[(3-phenoxyphenyl)methyl]aniline
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: BEIORKBMNIPTFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-phenyl-m-phenoxybenzylideneamine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以80%的产率得到N-phenyl-m-phenoxybenzylamine
  参考文献：
  名称：

  Synthesis and Reactions of Azomethines Containing a m-Phenoxyphenyl Group: II. Chemical Transformations >of N-Aryl-m-phenoxyphenylmethanimines and Arylhydrazones of m-Phenoxybenzaldehyde

  摘要：

  Chemical transformations of N-aryl-m-phenoxyphenylmethanimines and m-phenoxybenzaidehyde arythydrazones were studied by examples of reduction thereof with complex metal hydrides and reactions with dialkyl phosphates and dialkyl phosphites.

  DOI：

  10.1023/b:rujo.0000043714.74375.30

文献信息

• A nanoscale iron catalyst for heterogeneous direct <i>N</i>- and <i>C</i>-alkylations of anilines and ketones using alcohols under hydrogen autotransfer conditions
  作者：Madhu Nallagangula、Chandragiri Sujatha、Venugopal T. Bhat、Kayambu Namitharan

  DOI：10.1039/c9cc04120f

  日期：——

  report a commercially available nanoscale Fe catalyst for heterogeneous direct N- and C-alkylation reactions of anilines and methyl ketones with alcohols. A hydrogen autotransfer mechanism has been found to operate in these reactions by deuterium labelling studies. In addition, dehydrogenative quinoline synthesis has been demonstrated from amino benzyl alcohols and acetophenones.

  在这里，我们报告了一种可商购的纳米级Fe催化剂，用于苯胺和甲基酮与醇的异质直接N-和C-烷基化反应。通过氘标记研究，发现氢自动转移机制在这些反应中起作用。另外，已经证明从氨基苄醇和苯乙酮合成脱氢喹啉。
• A conjugated ketone as a catalyst in alcohol amination reactions under transition-metal and hetero-atom free conditions
  作者：Xingchao Dai、Xinjiang Cui、Youquan Deng、Feng Shi

  DOI：10.1039/c5ra07681a

  日期：——

  Here, we show the results of a molecular-defined conjugated ketone catalyzed alcohol amination reaction. Under the optimized reaction conditions, the yields to the desired products reached 98%. The reaction mechanism and kinetic study supposed that carbonyl–hydroxyl groups are the catalytically active sites, and the transfer-hydrogenation reactions progress via the recycling of carbonyl and hydroxyl

  在这里，我们显示了分子定义的共轭酮催化的醇胺化反应的结果。在优化的反应条件下，所需产物的产率达到98％。反应机理和动力学研究认为羰基-羟基是催化活性位点，转移加氢反应是通过羰基和羟基的循环进行的。催化过程显示出有望成为乙醇胺化反应的一种有效而经济的途径。
• Insight into O₂-Promoted Base-Catalyzed<i>N</i>-Alkylation of Amines with Alcohols
  作者：Chao Wang、Changpeng Chen、Jian Han、Jingyu Zhang、Yingming Yao、Yingsheng Zhao

  DOI：10.1002/ejoc.201500086

  日期：2015.5

  efficient and practical transition-metal-free CsOH/O2 catalyst system was developed for the N-alkylation of amines with alcohols under argon. This strategy was compatible with many alcohols and exhibits excellent functional group tolerance. More significantly, the selective formation of secondary amines was achieved in excellent yields. The detailed mechanistic study gave a clear understanding of the role

  开发了一种高效实用的不含过渡金属的 CsOH/O2 催化剂体系，用于在氩气下用醇对胺进行 N-烷基化。该策略与许多醇相容，并表现出优异的官能团耐受性。更重要的是，仲胺的选择性形成以极好的收率实现。详细的机理研究清楚地了解了碱和氧在催化循环中的作用。
• Zinc‐Catalyzed N‐Alkylation of Aromatic Amines with Alcohols: A Ligand‐Free Approach
  作者：Velayudham Sankar、Murugavel Kathiresan、Bitragunta Sivakumar、Subramaniyan Mannathan

  DOI：10.1002/adsc.202000499

  日期：2020.10.21

  N‐alkylation reaction of aromatic amines was achieved using aliphatic, aromatic, and heteroaromatic alcohols as the alkylating reagent. A variety of aniline derivatives, including heteroaromatic amines, underwent the N‐alkylation reaction and furnished the corresponding monoalkylated products in good to excellent yields. The application of the reaction is also further demonstrated by the synthesis of a 2‐phenylquinoline

  使用脂肪族，芳香族和杂芳香族醇作为烷基化试剂，可以实现锌的芳香胺的N烷基化反应。各种杂苯胺衍生物，包括杂芳族胺，都经过了N-烷基化反应，并以良好的产率提供了相应的单烷基化产物。由苯乙酮和2-氨基苄醇合成2-苯基喹啉衍生物也进一步证明了该反应的应用。氘标记实验表明，反应是通过借用氢过程进行的。
• Catalytic Hydroboration and Reductive Amination of Carbonyl Compounds by HBpin using a Zinc Promoter
  作者：Ravi Kumar、Parveen Rawal、Indrani Banerjee、Hari Pada Nayek、Puneet Gupta、Tarun K. Panda

  DOI：10.1002/asia.202200013

  日期：2022.3

  Chemoselective hydroboration of aldehydes and ketones with HBpin catalyzed by iminopyridine supported zinc(II) complex under ambient conditions is reported.

  报道了在环境条件下由亚氨基吡啶负载的锌 (II) 络合物催化的醛和酮与 HBpin 的化学选择性硼氢化反应。