N,N-divinylethylamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-divinylethylamine
• 英文别名: N,N-bis(ethenyl)ethanamine
• 化学式: C₆H₁₁N
• 分子量: 97.16
• InChiKey: TVYQYOWWDPJXTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三乙胺 在 [(1,3-bis((di-tert-butylphosphino)methyl)benzene(-1H))IrH2] 3,3-二甲基-1-丁烯 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 生成 N,N-diethylvinylamine 、 N,N-divinylethylamine
  参考文献：
  名称：

  Novel synthesis of enamines by iridium-catalyzed dehydrogenation of tertiary aminesElectronic supplementary information (ESI) available: detailed experimental procedures and spectroscopic information. See http://www.rsc.org/suppdata/cc/b3/b304357f/

  摘要：

  报道了一种新的获得烯胺的途径，即“三元胺在铱催化剂的“钳状配体”催化下脱氢”。

  DOI：

  10.1039/b304357f

文献信息

• Novel synthesis of enamines by iridium-catalyzed dehydrogenation of tertiary aminesElectronic supplementary information (ESI) available: detailed experimental procedures and spectroscopic information. See http://www.rsc.org/suppdata/cc/b3/b304357f/
  作者：Xiawei Zhang、Amy Fried、Spencer Knapp、Alan S. Goldman

  DOI：10.1039/b304357f

  日期：——

  A novel route to enamines is reported, the dehydrogenation of tertiary amines catalyzed by a “pincer-ligated” iridium catalyst.

  报道了一种新的获得烯胺的途径，即“三元胺在铱催化剂的“钳状配体”催化下脱氢”。
• Catalytic dehydrogenation of cyclooctane and triethylamine using aliphatic iridium pincer complexes
  作者：Alexey V. Polukeev、Roman Gritcenko、Klara J. Jonasson、Ola F. Wendt

  DOI：10.1016/j.poly.2014.06.016

  日期：2014.12

  The majority of the known pincer iridium based catalysts for dehydrogenation of alkanes has arene-based backbones. Here, the catalytic activity of aliphatic iridium pincer complexes, viz, the cyclohexane-based phosphine complex (PCyP)IrHCl (4) (PCyP = cis-1,3-bis-[(di-tert-butylphosphino)methyl]cyclohexane}(-)) and the 2-methylpropane-based phosphinite complex (POCOP)IrHCl (5) (POCOP = 1,3-bis-(di-tert-butyl-phosphinito)-2-methylpropane(-)), in dehydrogenation of cyclooctane and triethylamine was studied. They give TONs that are in the range of 0-200. In addition, improved procedures for synthesis and metallation of the PCyP ligand (3) are presented. (C) 2014 Elsevier Ltd. All rights reserved.
• Formation of Enamines via Catalytic Dehydrogenation by Pincer-Iridium Complexes
  作者：Yansong J. Lu、Xiawei Zhang、Santanu Malakar、Karsten Krogh-Jespersen、Faraj Hasanayn、Alan S. Goldman

  DOI：10.1021/acs.joc.9b02846

  日期：2020.3.6

  lesser crowding of the di-isopropylphosphino-substituted catalysts. Experimentally determined kinetic isotope effects in conjunction with DFT-based analysis support a dehydrogenation mechanism involving initial pre-equilibrium oxidative addition of the amine α-C-H bond followed by rate-determining elimination of the β-C-H bond.

  发现二异丙基膦基取代的夹钳连接的铱催化剂对于简单叔胺的脱氢以产生烯胺比先前报道的二叔丁基膦基取代的物种明显更有效。还发现，二异丙基膦基取代的配合物催化几种β-官能化叔胺的脱氢反应，得到相应的1，2-二官能化烯烃。二叔丁基膦基取代的物质对这种底物无效；据推测，明显的差异归因于二异丙基膦基取代的催化剂较少的拥挤。