N-cinnamyl-naphthylamine | 22774-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-cinnamyl-naphthylamine
• 英文别名: N-cinnamyl-α-naphthylamine；naphthalen-1-yl-(3-phenyl-allyl)-amine；Cinnamyl-1-naphthylamin；N-(3-phenylprop-2-enyl)naphthalen-1-amine
• CAS: 22774-95-4
• 化学式: C₁₉H₁₇N
• 分子量: 259.351
• InChiKey: CYLXFMNXWCACBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-cinnamyl-naphthylamine 在 氧气 、 tris(p-bromophenylammoniumyl) hexachloroantimonate 作用下， 以 乙腈 为溶剂， 反应 46.0h， 以64%的产率得到2-phenylbenzo[h]quinoline
  参考文献：
  名称：

  从N-肉桂基苯胺到sp3 C的2-芳基喹啉的意外构造？催化自由基阳离子盐诱导的H有氧氧化

  摘要：

  cinnamylanilines的一个意想不到的反应物通过的自由基阳离子盐诱导有氧氧化实现SP 3 Ç  H键，从而提供了一系列的2- arylquinolines。机理研究表明，肉桂基苯胺被氧化成亚胺，亚胺被相应的亚胺分解生成的苯胺攻击。进一步分子内环化和芳构化后，获得了2-芳基喹啉。该反应提供了一种从容易获得的起始原料中构建2-芳基喹啉的新方法。

  DOI：

  10.1002/adsc.201500574
• 作为产物：
  描述：

  N-(3-phenylallylidene)naphthalene-1-amine 在 二甲基苯基硅烷 、 gold 、 水 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以67%的产率得到N-cinnamyl-naphthylamine
  参考文献：
  名称：

  Exclusive Chemoselective Reduction of Imines in the Coexistence of Aldehydes Using AuNPore Catalyst

  摘要：

  Aldimines ((RHC)-H-1=NR2) were reduced in the coexistence of aldehydes ((RCHO)-C-1) with 100% chemoselectivity by the use of AuNPore giving corresponding amines ((RH2C)-H-1-NHR2) in high chemical yields.

  DOI：

  10.1021/ol500958p

文献信息

• pH-Mediated Selective Synthesis of N-Allylic Alkylation or N-Alkylation Amines with Allylic Alcohols via an Iridium Catalyst in Water
  作者：Nianhua Luo、Yuhong Zhong、Hongling Shui、Renshi Luo

  DOI：10.1021/acs.joc.1c01930

  日期：2021.11.5

  Amination of allylic alcohols is an effective approach in the facile synthesis of N-allylic alkylation or N-alkylation amines. Recently, a series of catalysts were devised to push forward this transformation. However, current synthetic methods are typically limited to achieve either N-allylic alkylation or N-alkylation products via a certain catalyst. In this article, a pH-mediated selective synthesis of N-allylic

  烯丙醇的胺化是一种简便合成N-烯丙基烷基化或N-烷基化胺的有效方法。最近，设计了一系列催化剂来推动这一转变。然而，目前的合成方法通常仅限于通过某种催化剂获得N-烯丙基烷基化或N-烷基化产物。在本文中，揭示了通过铱催化剂以水作为环境友好溶剂，选择性合成N-烯丙基烷基化或N-烷基化胺与烯丙基醇，从而实现N-烯丙基烷基化和N-烷基化产物的高产率。此外，具有低催化剂负载的克级实验提供了获得用于合成抗真菌药物萘替芬的独特入口的潜力。
• Thermal Rearrangement of<i>N</i>-(Substituted allyl)-1-naphthylamines
  作者：Seisaku Inada、Ryu-ichiro Kurata

  DOI：10.1246/bcsj.54.1581

  日期：1981.5

  The title reaction was examined and the results were compared with those of the thermal reaction of the corresponding N-tosyl derivatives.

  检查标题反应并将结果与​​相应 N-甲苯磺酰基衍生物的热反应结果进行比较。
• PEG-4000-promoted palladium-catalyzed <i>N</i> -allylation in water: aminonaphthalene as an example
  作者：Chun-Jen Shih、Yi-Jen Shue、Shiang-Yu Yang、Shyh-Chyun Yang

  DOI：10.1002/aoc.2899

  日期：2012.10

  process using palladium associated with ligands in a PEG4000–water system leading to N‐allylation was described in this study. PEG‐4000 was found to improve the palladium‐catalyzed allylic amination of allylic acetates with aminonaphthalenes and gave overall good to high yields of the corresponding N‐allylic aminonaphthalenes. Copyright © 2012 John Wiley & Sons, Ltd.

  在这项研究中描述了一种环境友好，高效的催化过程，该过程使用钯与PEG4000-水系统中的配体缔合，从而导致N-烯丙基化。发现PEG-4000可以改善钯催化的烯丙基乙酸酯与氨基萘的烯丙基胺化反应，并且可以使相应的N-烯丙基氨基萘的收率总体提高。版权所有©2012 John Wiley＆Sons，Ltd.
• Pd(OAc)2/dppf as an efficient and highly active catalyst for the allylation of amines, alcohols and carboxylic acids with 1-phenyl-1-propyne
  作者：Yogesh S. Wagh、Dinesh N. Sawant、Pawan J. Tambade、Kishor P. Dhake、Bhalchandra M. Bhanage

  DOI：10.1016/j.tet.2011.02.008

  日期：2011.4

  Pd(OAc)(2)/1,1'-bis(diphenylphosphino)ferrocene as an efficient, highly active catalyst for the allylation of amines, alcohols and carboxylic acids with 1-phenyl-1-propyne has been developed. The effect of various reaction parameters, such as ligand, time, solvent, temperature, metal: ligand ratio and catalyst concentration on yields of the product were investigated. The optimized procedure works well under mild operating conditions and permits rapid generation of a library for various allylated products. (C) 2011 Elsevier Ltd. All rights reserved.
• Vizgert,R.V. et al., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 914 - 919
  作者：Vizgert,R.V. et al.

  DOI：——

  日期：——