2-(2-Ethyl-butylidene)-malononitrile | 265108-11-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(2-Ethyl-butylidene)-malononitrile
• 英文别名: 2-(2-Ethylbutylidene)propanedinitrile
• CAS: 265108-11-0
• 化学式: C₉H₁₂N₂
• 分子量: 148.208
• InChiKey: UOTSFWSCUOMUFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-Ethyl-butylidene)-malononitrile 在 ammonium acetate 、 氨 、 对甲苯磺酸 、 丙二腈 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 5-(1-Ethyl-propyl)-7-(6-morpholin-4-yl-pyridin-3-yl)-pyrido[2,3-d]pyrimidin-4-ylamine
  参考文献：
  名称：

  Structure–activity studies of 5-substituted pyridopyrimidines as adenosine kinase inhibitors

  摘要：

  The synthesis and SAR of a novel series of non-nucleoside pyridopyrimidine inhibitors of the enzyme adenosine kinase (AK) are described. It was found that pyridopyrimidines with a broad range of medium and large non-polar substituents at the 5-position potently inhibited AK activity. A narrower range of analogues was capable of potently inhibiting adenosine phosphorylation in intact cells indicating an enhanced ability of these analogues to penetrate cell membranes. Potent AK inhibitors were found to effectively reduce nociception in animal models of thermal hyperalgesia and persistent pain. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00602-8
• 作为产物：
  描述：

  2-乙基丁醛 、 丙二腈 在 吗啉 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 2-(2-Ethyl-butylidene)-malononitrile
  参考文献：
  名称：

  Aliphatic aldehydes in multicomponent syntheses of 4-alkyl-substituted partially hydrogenated quinolines, fused 4H-pyrans, and 2-amino-4-ethyl-5-methylbenzene-1,3-dicarbonitrile

  摘要：

  The Knoevenagel condensation of aliphatic aldehydes with CH acids, malonodinitrile, cyanothioacetamide, cyclohexane-1,3-dione, dimedone, 4-hydroxycoumarin, 3-aminophenol, and N-(cyclohex-1-enyl)morpholine leads to formation of 4-alkyl-substituted partially hydrogenated quinolines, fused 4H-pyrans, and 2-amino-4-ethyl-5-methylbenzene-1,3-dicarbonitrile. The structure of the latter was proved by the X-ray diffraction data.

  DOI：

  10.1134/s1070428006040142

文献信息

• One-pot cascade assembling of 3-substituted tetracyanocyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action
  作者：Anatolii N. Vereshchagin、Michail N. Elinson、Nikita O. Stepanov、Gennady I. Nikishin

  DOI：10.1016/j.mencom.2009.11.010

  日期：2009.11

  The new cascade reaction was found: the formation of cyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action; the action of aqueous bromine on the equal amounts of alkylidenemalononitriles and malononitrile in EtOH–H 2 O solutions results in the formation of 3-substituted 1,1,2,2-tetracyanocyclopropanes in 55–98% yields.

  发现了新的级联反应：仅通过溴的直接作用，由亚烷基丙二腈和丙二腈形成环丙烷。在EtOH–H 2 O溶液中溴水溶液对等量的亚烷基丙二腈和丙二腈的作用导致形成3–取代的1,1,2,2-四氰基环丙烷，产率为55–98％。
• Synthesis of di/trifluoromethyl cyclopropane-dicarbonitriles <i>via</i> [2+1] annulation of fluoro-based diazoethanes with (alkylidene)malononitriles
  作者：Cheng-Feng Gao、Yue-Ji Chen、Jing Nie、Fa-Guang Zhang、Chi Wai Cheung、Jun-An Ma

  DOI：10.1039/d3cc03897a

  日期：——

  Herein, we describe a [2+1] annulation reaction of di/trifluorodiazoethane with (alkylidene)malononitriles. This protocol offers a streamlined synthesis of a wide range of stereospecific and densely functionalized difluoromethyl and trifluoromethyl cyclopropane-1,1-dicarbonitriles. Further functional group interconversions or skeletal elaborations afford structurally distinct cyclopropyl variants.

  在此，我们描述了二/三氟重氮乙烷与(亚烷基)丙二腈的[2+1]环化反应。该方案提供了多种立体特异性和密集功能化的二氟甲基和三氟甲基环丙烷-1,1-二甲腈的简化合成。进一步的官能团互变或骨架加工提供了结构上不同的环丙基变体。