dicyclohexylammonium 2-cyanoacrylate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: dicyclohexylammonium 2-cyanoacrylate
• 英文别名: Dicyclohexylamine 2-cyanoacrylate；2-cyanoprop-2-enoic acid;N-cyclohexylcyclohexanamine
• 化学式: C₄H₃NO₂*C₁₂H₂₃N
• 分子量: 278.395
• InChiKey: KBUNPAIJSVOOSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丁二酰亚胺 、 dicyclohexylammonium 2-cyanoacrylate 以 二氯甲烷 为溶剂， 反应 48.0h， 以74%的产率得到2-Cyano-3-(2,5-dioxopyrrolidin-1-yl)propanoate;dicyclohexylazanium
  参考文献：
  名称：

  Nitrogen Pronucleophiles in the Self-Catalytic Michael Reaction

  摘要：

  The self-catalytic Michael reaction of several nitrogen pronucleophiles with dicyclohexylammonium 2-diethylphosphonoacrylate and dicyclohexylammonium 2-cyanoacrylate proceeded highly efficiently at room temperature to give the corresponding 1,4-adducts.

  DOI：

  10.1080/00397910008087224
• 作为产物：
  描述：

  聚合甲醛 、 氰乙酸 、 二环己胺 在 三乙胺 作用下， 以 苯 为溶剂， 反应 0.33h， 以75%的产率得到dicyclohexylammonium 2-cyanoacrylate
  参考文献：
  名称：

  Self-Catalytic Michael Reaction, An Efficient Route to 2-Cyanoalkanoic Acids

  摘要：

  The self - catalytic Michael reaction of several 1,3-dicarbonyl compounds with dicyclohexylammonium 2-cyanoacrylate proceeded highly efficiently at room temperature to give the corresponding 1,4-adducts.

  DOI：

  10.1080/00397910008087367

文献信息

• ALPHA-CYANOACRYLATE ESTER SYNTHESIS
  申请人：Henkel Ireland Limited

  公开号：US20130171092A1

  公开（公告）日：2013-07-04

  The high temperatures required for cracking the cyanoacrylate oligomers, produced by the Knovenagel condensation of formaldehyde and a cyanoacetate, limit the synthetic diversity and the number of different side chains that can be incorporated into a cyanoacrylate prepared using this method. Accordingly, the diversity of cyanoacrylate monomers prepared industrially is quite limited. Disclosed herein is a method for the preparation of alpha-Cyanoacrylate ester monomers from a variety of phosphonium and ammonium alpha-cyanoacrylate salts. The phosphonium and ammonium alpha-cyanoacrylate salts are of the general formula:

  产生于甲醛和氰乙酸酯的Knovenagel缩合反应的氰丙烯酸酯寡聚体裂解所需的高温限制了使用该方法制备的氰丙烯酸酯中可以纳入的不同侧链的数量和合成多样性。因此，工业上制备的氰丙烯酸酯单体的多样性相当有限。本文公开了一种从各种磷铵和铵盐α-氰丙烯酸酯制备α-氰丙烯酸酯单体的方法。这些磷铵和铵盐α-氰丙烯酸酯的一般化学式为：
• [EN] ALPHA-CYANOACRYLATE ESTER SYNTHESIS<br/>[FR] SYNTHÈSE D'ESTERS D'ALPHA-CYANOACRYLATE
  申请人：LOCTITE R & D LTD

  公开号：WO2012041395A1

  公开（公告）日：2012-04-05

  The high temperatures required for cracking the cyanoacrylate oligomers, produced by the Knovenagel condensation of formaldehyde and a cyanoacetate, limit the synthetic diversity and the number of different side chains that can be incorporated into a cyanoacrylate prepared using this method. Accordingly, the diversity of cyanoacrylate monomers prepared industrially is quite limited. Disclosed herein is a method for the preparation of alpha-Cyanoacrylate ester monomers from a variety of phosphonium and ammonium alpha-cyanoacrylate salts. The phosphonium and ammonium alpha-cyanoacrylate salts are of the general formula: (I).

  通过Knovenagel缩合反应产生的氰丙烯酸酯寡聚体裂解所需的高温限制了合成多样性和可用于使用该方法制备的氰丙烯酸酯中所包含的不同侧链的数量。因此，工业上制备的氰丙烯酸酯单体的多样性相当有限。本文披露了一种从各种磷铵和铵盐氰丙烯酸酯制备α-氰丙烯酸酯单体的方法。磷铵和铵盐氰丙烯酸酯的一般化学式为：(I)。
• C-Alkylation of hydroxyarenes by Michael reaction
  作者：Henryk Krawczyk、Ryszard Bodalski

  DOI：10.1039/b101210j

  日期：——

  Electron-rich hydroxyarenes undergo self-catalytic Michael reaction with the dicyclohexylammonium acrylate 1. The regiochemistry of this reaction is markedly dependent on structural features of the starting hydroxyarenes. While at 25 °C and in nonpolar solvents phenol and most of its monosubstituted derivatives are converted into the corresponding O-adducts, conjugate addition of disubstituted phenols and naphthols leads to the C-adducts exclusively. An analogous reaction pattern is observed with the dicyclohexylammonium acrylate 2 as the Michael acceptor.

  富电子羟基芳烃与丙烯酸二环己胺1发生自催化迈克尔反应。该反应的立体化学明显取决于起始羟基芳烃的结构特征。在25°C和非极性溶剂中，苯酚及其大部分单取代衍生物转化为相应的O-加合物，而二取代苯酚和萘酚的共轭加成则仅产生C-加合物。以丙烯酸二环己胺2作为迈克尔受体时，观察到类似的反应模式。
• Nitrogen Pronucleophiles in the Self-Catalytic Michael Reaction
  作者：Henryk Krawczyk

  DOI：10.1080/00397910008087224

  日期：2000.4

  The self-catalytic Michael reaction of several nitrogen pronucleophiles with dicyclohexylammonium 2-diethylphosphonoacrylate and dicyclohexylammonium 2-cyanoacrylate proceeded highly efficiently at room temperature to give the corresponding 1,4-adducts.
• Self-Catalytic Michael Reaction, An Efficient Route to 2-Cyanoalkanoic Acids
  作者：Henryk Krawczyk

  DOI：10.1080/00397910008087367

  日期：2000.2

  The self - catalytic Michael reaction of several 1,3-dicarbonyl compounds with dicyclohexylammonium 2-cyanoacrylate proceeded highly efficiently at room temperature to give the corresponding 1,4-adducts.