N¹, N⁴-dicyclohexylfumaramide | 873295-56-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N¹, N⁴-dicyclohexylfumaramide
• 英文别名: N.N'-dicyclohexyl-fumaramide；N.N'-Dicyclohexyl-fumaramid；(2E)-N1,N4-Dicyclohexyl-2-butenediamide；(E)-N,N'-dicyclohexylbut-2-enediamide
• CAS: 873295-56-8
• 化学式: C₁₆H₂₆N₂O₂
• 分子量: 278.395
• InChiKey: CPDYQLDEBJQAPQ-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-环己基丙-2-烯酰胺 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到N¹, N⁴-dicyclohexylfumaramide
  参考文献：
  名称：

  Efficient synthesis of fumaric amides through cross-metathesis of acrylic amides with the NHC Grubbs ruthenium catalyst

  摘要：

  Application of the second generation Grubbs metathesis catalyst for the homo-cross-metathesis of acroyl amides from chiral amines is reported. This efficient and high-yielding reaction provides a side-product free synthesis of fumaric acid diamides which are formed with complete (E)-selectivity under the reaction conditions. In particular, products which cannot be synthesized from the corresponding fumaroyl chloride via classic condensation route can now be provided in excellent yields (88-98%) with a catalyst loading from 2.5 mol% to even 0.375 mol%. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.07.116

文献信息

• Self-assembly of small-molecule fumaramides allows transmembrane chloride channel formation
  作者：Arundhati Roy、Amitosh Gautam、Javid Ahmad Malla、Sohini Sarkar、Arnab Mukherjee、Pinaki Talukdar

  DOI：10.1039/c7cc08693h

  日期：——

  Intermolecular hydrogen bonding of N¹,N⁴-dicyclohexylfumaramide favors the formation of self-assembled ion channels, which facilitates selective Cl⁻ transport across a lipid bilayer membrane.

  N1，N4-二环己基富马酰胺的分子间氢键有利于形成自组装离子通道，从而促进氯离子在脂质双分子层膜上的选择性传输。
• A New Reaction of Nitriles. III. Amides from Dinitriles
  作者：Frederic R. Benson、John J. Ritter

  DOI：10.1021/ja01180a075

  日期：1949.12
• Efficient synthesis of fumaric amides through cross-metathesis of acrylic amides with the NHC Grubbs ruthenium catalyst
  作者：Jan Streuff、Kilian Muñiz

  DOI：10.1016/j.jorganchem.2005.07.116

  日期：2005.12

  Application of the second generation Grubbs metathesis catalyst for the homo-cross-metathesis of acroyl amides from chiral amines is reported. This efficient and high-yielding reaction provides a side-product free synthesis of fumaric acid diamides which are formed with complete (E)-selectivity under the reaction conditions. In particular, products which cannot be synthesized from the corresponding fumaroyl chloride via classic condensation route can now be provided in excellent yields (88-98%) with a catalyst loading from 2.5 mol% to even 0.375 mol%. (c) 2005 Elsevier B.V. All rights reserved.