2-Cyclopentylmethylene-malononitrile | 265108-12-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Cyclopentylmethylene-malononitrile
• 英文别名: 2-(Cyclopentylmethylidene)propanedinitrile
• CAS: 265108-12-1
• 化学式: C₉H₁₀N₂
• 分子量: 146.192
• InChiKey: VBMQLZGRVMOPMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• 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-Cyclopentylmethylene-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-Cyclopentyl-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：

  环戊基甲醛 、 丙二腈 以 乙醇 为溶剂， 生成 2-Cyclopentylmethylene-malononitrile
  参考文献：
  名称：

  蓝光触发 CC 键形成，以 CBr4 为光催化剂合成功能性丙二腈

  摘要：

  由丙二腈衍生的具有环状结构的化合物在制药领域至关重要。在此，我们开发了一种简便的合成方案，在温和且环保的条件下，使用 CBr 4作为光催化剂，通过光触发烷基化得到功能性丙二腈衍生物。以丰富的乙烯丙二腈与四氢呋喃为底物，通过形成新的CC键发生无金属偶联反应。该反应显示出广泛的范围，对各种官能团的耐受性和合理的产率。借助 DFT 计算进行的机理研究表明，这种反应采取了激进的途径。我们期望该协议成为无金属 C C 偶联反应的有用平台。

  DOI：

  10.1016/j.tetlet.2023.154837

文献信息

• High Surface Area MgO as a Highly Effective Heterogeneous Base Catalyst for Michael Addition and Knoevenagel Condensation Reactions
  作者：Graham J. Hutchings、Chunli Xu、Jonathan K. Bartley、Dan I. Enache、David W. Knight

  DOI：10.1055/s-2005-918467

  日期：——

  Magnesium oxide (MgO), obtained using a novel but simple procedure, was systematically investigated as a heterogeneous base catalyst for reactions taking place in the liquid phase, specifically the Michael addition and the Knoevenagel condensation. The activity of MgO was studied in detail, together with the effects of solvent and substrate on the catalytic activity for each type of reaction. A key finding is that the formation of enols affected the activity of MgO. The experimental results show that the activity of MgO did not change when it was reused and it is an excellent heterogeneous catalyst for the reactions studied.

  氧化镁（MgO）采用了一种新颖但简单的制备方法，被系统地研究作为液相反应的非均相碱催化剂，具体涉及Michael加成反应和Knoevenagel缩合反应。详细探讨了MgO的活性，以及溶剂和底物对每类反应催化活性的影响。一个关键发现是，烯醇化物的形成影响了MgO的活性。实验结果表明，MgO在重复使用时活性未发生变化，它是所研究反应的一种优秀非均相催化剂。
• 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。
• Structure–activity studies of 5-substituted pyridopyrimidines as adenosine kinase inhibitors
  作者：Marlon Cowart、Chih-Hung Lee、Gregory A. Gfesser、Erol K. Bayburt、Shripad S. Bhagwat、Andrew O. Stewart、Haixia Yu、Kathy L. Kohlhaas、Steve McGaraughty、Carol T. Wismer、Joseph Mikusa、Chang Zhu、Karen M. Alexander、Michael F. Jarvis、Elizabeth A. Kowaluk

  DOI：10.1016/s0960-894x(00)00602-8

  日期：2001.1

  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.