N,N-二烯丙基萘-1-胺 | 30438-97-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N,N-二烯丙基萘-1-胺
• 英文名称: N,N-diallyl-1-naphthylamine
• 英文别名: N,N-diallylnaphthalen-1-amine；N,N-bis(prop-2-enyl)naphthalen-1-amine
• CAS: 30438-97-2
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: UKACWJFNPSCMPG-UHFFFAOYSA-N

物化性质

• 沸点：
  329.0±31.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-二烯丙基萘-1-胺 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 生成 2-bromo-N,N-bis(prop-2-enyl)naphthalen-1-amine
  参考文献：
  名称：

  10.1055/3-0028-1083311

  摘要：

  DOI：

  10.1055/3-0028-1083311
• 作为产物：
  描述：

  1-叠氮基萘 、 3-溴丙烯 在 tris(dibenzylideneacetone)dipalladium (0) tin(ll) chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.17h， 以87%的产率得到N,N-二烯丙基萘-1-胺
  参考文献：
  名称：

  SnCl2 mediated efficient N,N-dialkylation of azides to tertiary-amine via potential stannaimine intermediate

  摘要：

  A base free one-pot conversion of azides to N,N-dialkylamine is described. A two-step reaction pathway has been postulated invoking the intermediacy of stannaimine. This new carbon-nitrogen bond formation strategy adds to the repertoire of tin(II) chemistry. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.12.017

文献信息

• Synthesis of medium-sized aryl-fused nitrogenous heterocycles <i>via</i> sequential aryne aza-Claisen rearrangement/ring-closing metathesis
  作者：N. S. V. M. Rao Mangina、Ravinder Guduru、Galla V. Karunakar

  DOI：10.1039/c7ob03166a

  日期：——

  The reaction of arynes and secondary allylamines furnished ortho-allyl-substituted N-arylanilines via an aza-Claisen rearrangement. In this transformation, the sequential formation of C–C and C–N bonds occurred by involving two aryne molecules under metal-free reaction conditions to provide moderate to good yields of the products. The obtained ortho-allyl-substituted N-arylaniline derivatives were

  芳烃和仲烯丙胺的反应通过氮杂-克莱森重排提供邻-烯丙基取代的N-芳基苯胺。在这种转化过程中，通过在无金属反应条件下使两个芳烃分子参与进来，从而形成了C–C和C–N键的顺序形成，从而提供了中等至良好的收率。获得的邻烯丙基取代的N-芳基苯胺衍生物通过闭环复分解（RCM）进一步转化为芳基稠合的中等大小（7-9）含氮杂环分子，例如氮杂，氮杂和苯丙氨酸。
• Synthesis of Pyrrole Derivatives from Diallylamines by One-Pot Tandem Ring-Closing Metathesis and Metal-Catalyzed Oxidative Dehydrogenation
  作者：Weiqiang Chen、Jianhui Wang

  DOI：10.1021/om400046r

  日期：2013.3.25

  A series of aryl-substituted pyrrole derivatives was synthesized from diallylamines through a ruthenium carbene catalyzed ring-closing metathesis reaction and in situ oxidative dehydrogenation reaction catalyzed by FeCl3·6H2O or CuCl2·2H2O in the presence of O2. The reaction was mild, simple, and convenient. An oxygen atmosphere played a critical role in obtaining high conversion of substituted pyrroles

  在O 2存在下，通过钌卡宾催化的闭环复分解反应和FeCl 3 ·6H 2 O或CuCl 2 ·2H 2 O催化的原位氧化脱氢反应，由二烯丙基胺合成了一系列芳基取代的吡咯衍生物。反应温和，简单，方便。在拟议的催化体系中，氧气气氛对于获得高取代的吡咯转化率起着至关重要的作用。
• Direct palladium(0)-catalyzed amination of allylic alcohols with aminonaphthalenes
  作者：Yi-Jen Shue、Shyh-Chyun Yang、Hwe-Chen Lai

  DOI：10.1016/s0040-4039(02)02861-7

  日期：2003.2

  The direct activation of CO bonds in allylic alcohols by palladium complexes has been accelerated by carrying out the reactions in the presence of titanium reagents. The palladium-catalyzed amination of allylic alcohols using aminonaphthalenes gave N-allylic naphthylamines in good yields. The monoallylation products are formed in the main.

  通过在钛试剂的存在下进行反应，已经加速了钯配合物在烯丙基醇中对CO键的直接活化。使用氨基萘的钯催化的烯丙基醇的胺化以良好的收率得到了N-烯丙基萘胺。单烯丙基化产物在主体中形成。
• 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.
• Cobalt-Catalyzed Cycloisomerization of N,N-Diallylanilines
  作者：Jun Liu、Zhanhui Yang、Minfang Zheng、Hongfei Wu、Ning Chen、Jiaxi Xu

  DOI：10.1055/s-0037-1611832

  日期：2019.9

  efficient bench-stable catalysts for the oligomerization of ethylenes. Herein, their further application was developed in the catalytic transformation of N,N-diallylanilines to pyrrolidines through a cycloisomerization process. In this protocol, chlorobenzene is a vital additive to promote reaction efficiency. Cobalt catalysts bearing 2-imino-1,10-phenanthroline ligands are quite efficient bench-stable catalysts

  抽象的 带有2-亚氨基-1，10-菲咯啉配体的钴催化剂是用于乙烯低聚的非常有效的台稳催化剂。在本文中，它们的进一步应用被开发为通过环异构化过程将N，N-二烯丙基苯胺催化转化为吡咯烷。在该协议中，氯苯是提高反应效率的重要添加剂。 带有2-亚氨基-1，10-菲咯啉配体的钴催化剂是用于乙烯低聚的非常有效的台稳催化剂。在本文中，它们的进一步应用被开发为通过环异构化过程将N，N-二烯丙基苯胺催化转化为吡咯烷。在该协议中，氯苯是提高反应效率的重要添加剂。