2-(1-phenyl-2-(quinolin-2-yl)ethyl)malononitrile | 1416848-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(1-phenyl-2-(quinolin-2-yl)ethyl)malononitrile
• 英文别名: 2-(1-Phenyl-2-quinolin-2-ylethyl)propanedinitrile
• CAS: 1416848-96-8
• 化学式: C₂₀H₁₅N₃
• 分子量: 297.359
• InChiKey: NWZAPOBJLPCWRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基喹啉 、 苄烯丙二腈 在 ytterbium(III) triflate hydrate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以69%的产率得到2-(1-phenyl-2-(quinolin-2-yl)ethyl)malononitrile
  参考文献：
  名称：

  Lewis酸催化的sp 3 CH键与亚甲基丙二腈的共轭加成反应

  摘要：

  已经开发了通过sp 3 CH键官能化的路易斯酸催化的2-烷基氮杂芳烃到亚甲基丙二腈的共轭加成，其提供了将腈基结合到杂环中的有效和可靠的方法。

  DOI：

  10.1002/adsc.201200285

文献信息

• A Catalyst-Free, One-Pot, Three-Component Approach for the Synthesis of 2-[1-Aryl-2-(azaaryl)ethyl]malononitriles via sp3 C–H Activation of 2-Methyl Azaarenes
  作者：H. Meshram、Nandigama Kumar、L. Rao、N. JagadeeshBabu、V. Dileep Kumar、U. Murthy

  DOI：10.1055/s-0034-1380212

  日期：——

  Combinatorial libraries of 2-[1-aryl-2-(azaaryl)ethyl]malononitriles derivatives have been synthesized by catalyst-free, one-pot, three-component protocol and employing water as a solvent. Simple reaction, open air reaction, and easy isolation are added advantages of this method. The method is applicable for aryl as well as heteroaryl systems and provides a convenient access for the synthesis of novel quinoline

  2-[1-芳基-2-(氮杂芳基)乙基]丙二腈衍生物的组合文库已通过无催化剂、一锅、三组分方案和使用水作为溶剂合成。反应简单、露天反应、易分离是该方法的附加优点。该方法适用于芳基和杂芳基体系，为合成新型喹啉衍生物提供了方便的途径。评估了所有 2-[1-芳基-2-(氮杂芳基)乙基]丙二腈衍生物对革兰氏阳性菌（金黄色葡萄球菌、表皮葡萄球菌和蜡状芽孢杆菌）和革兰氏阴性菌（铜绿假单胞菌）的抗菌活性。11 种化合物对革兰氏阳性病原体和革兰氏阴性菌均表现出良好的抗菌活性。
• An addition of benzylic sp3 C–H to electron-deficient olefins
  作者：Hong-Ying Li、Li-Juan Xing、Tong Xu、Peng Wang、Rui-Hua Liu、Bin Wang

  DOI：10.1016/j.tetlet.2012.11.100

  日期：2013.2

  An addition of benzylic sp3 C-H to electron-deficient olefins has been developed. This reaction provides a new method for the benzylic C-H bond functionalization of azaarenes without using any catalyst and additives. (C) 2012 Elsevier Ltd. All rights reserved.
• Benzylic sp3 C-H Functionalization Reaction of 2-Methylazaarenes Catalyzed by Pepsin
  作者：Zong-Bo Xie、Zhang-Gao Le、Feng Ai、Guo-Qing Chen、Jiu-Jian Ji、Zhi-Qiang Zhu

  DOI：10.3987/com-18-13941

  日期：——

  In this work, the addition of 2-methylazaarenes benzylic sp(3) C-H to electron-deficient olefins, catalyzed by pepsin from pig gastric mucosa was reported. A series of azaarene derivatives (1 mmol) were obtained in good yields at 60 degrees C for 60 similar to 72 h with 20 mg pepsin as catalyst. This is a facile method and the reaction conditions are mild, which expands the application of biocatalysis in sp(3) C-H functionalization of azaarenes.
• PEG-400 mediated sp 3 C H functionalization of aza-arenes: an enroute to the synthesis of 2-(2-(6-methylpyridin/quinolin-2-yl)-1-phenylethyl)malononitriles
  作者：Raghu Mallepalli、Dinesh Kumar Reddy Vennam、Ramu Sridhar Perali

  DOI：10.1016/j.tetlet.2016.08.083

  日期：2016.10

  Polyethylene glycol (PEG-400) has been discovered to be an effective eco-friendly solvent cum activator for the one-pot coupling of 2,6-dimethyl-pyridine or 2-methylquinoline, malononitrile and aldehydes to produce aza-arene derivatives through a sp(3) bond functionalization. The reaction was performed under mild conditions and the generality of the one-pot reaction was investigated. (C) 2016 Elsevier Ltd. All rights reserved.