2-(2-fluoro-4-methylbenzylidene)malononitrile | 771570-09-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-fluoro-4-methylbenzylidene)malononitrile
• 英文别名: 2-[(2-Fluoro-4-methylphenyl)methylidene]propanedinitrile；2-[(2-fluoro-4-methylphenyl)methylidene]propanedinitrile
• CAS: 771570-09-3
• 化学式: C₁₁H₇FN₂
• 分子量: 186.188
• InChiKey: AQDNFWKTNYKOFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-5-((2-(2-(furan-2-yl)-1-nitrovinyl)-4,5-dihydro-1H-imidazol-1-yl)methyl)pyridine 、 2-(2-fluoro-4-methylbenzylidene)malononitrile 以 乙酸乙酯 为溶剂， 生成 1-[(6-Chloropyridin-3-yl)methyl]-5-(2-fluoro-4-methylphenyl)-7-(furan-2-yl)-8-nitro-2,3,5,7-tetrahydroimidazo[1,2-a]pyridine-6,6-dicarbonitrile
  参考文献：
  名称：

  Designing Tetrahydroimidazo[1,2-a]pyridine Derivatives via Catalyst-free Aza-Diels−Alder Reaction (ADAR) and Their Insecticidal Evaluation

  摘要：

  A series of tetrahydroimidazo[1,2-a]pyridine derivatives were synthesized by the reaction of 2-vinyl-4,5-dihydroimidazole derivatives with substituted benzylidenemalononitrile via a catalyst-free aza-Diels-Alder reaction. Insecticidal activities of target compounds were tested against pea aphids (Aphis craccivora), which showed that activities were strongly influenced by the substituents and their positions. Especially, the introduction of a fluoro group at the 2- position increased activities.

  DOI：

  10.1021/jf100645y
• 作为产物：
  描述：

  2-氟-4-甲基苯甲醛 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 1.33h， 生成 2-(2-fluoro-4-methylbenzylidene)malononitrile
  参考文献：
  名称：

  One-pot synthesis of polyfunctionalized 4H-pyran derivatives bearing fluorochloro pyridyl moiety

  摘要：

  Polyfunctionalized 4H-pyran derivatives bearing fluorochloro pyridyl moiety were readily prepared in high yields via one-pot multicomponent reaction catalyzed by piperidine. This present protocol provides an efficient synthetic route to the target compounds with the characteristics of short reaction time, high yield, and easy separation of the products. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.065

文献信息

• Design, Multicomponent Synthesis, and Bioactivities of Novel Neonicotinoid Analogues with 1,4-Dihydropyridine Scaffold
  作者：Wenwen Zhang、Xiaobao Yang、Weidong Chen、Xiaoyong Xu、Lu Li、Hongbin Zhai、Zhong Li

  DOI：10.1021/jf902034z

  日期：2010.3.10

  Novel neonicotinoid analogues bearing a 1,4-dihydropridine scaffold were designed and synthesized by multicomponent reactions (MCRs) to enhance pi-pi stacking. The synthesized compounds were identified by H-1 NMR, C-13 NMR, high-resolution mass spectroscopy, and elemental analysis. Bioassay tests showed that some of them exhibited high insecticidal activities against pea aphid (Aphis craccivora).
• Facile three-component synthesis and insecticidal evaluation of hexahydroimidazo[1,2-a]pyridine derivatives
  作者：Ye-Feng Fan、Wen-Wen Zhang、Xu-Sheng Shao、Zhi-Ping Xu、Xiao-Yong Xu、Zhong Li

  DOI：10.1016/j.cclet.2014.10.019

  日期：2015.1

  A series of new hexahydroimidazo[1,2-a]pyridine derivatives were synthesized via convenient and practical three-component reactions. Preliminary bioassays showed that majority of the target compounds exhibited moderate to excellent insecticidal activity against cowpea aphids (Aphis craccivora). Among them, compound 9I demonstrated significant activity with LC50 value of 0.00918 mmol/L which was about 3.8-fold higher than that of imidacloprid (IMI). Furthermore, the study of stereostructure-activity relationship of four isomers of 9k indicated that configuration played a key role in insecticidal activity of these compounds. (C) 2014 Zhong Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.
• One-pot synthesis of polyfunctionalized 4H-pyran derivatives bearing fluorochloro pyridyl moiety
  作者：Zhenjun Ye、Renbo Xu、Xusheng Shao、Xiaoyong Xu、Zhong Li

  DOI：10.1016/j.tetlet.2010.07.065

  日期：2010.9

  Polyfunctionalized 4H-pyran derivatives bearing fluorochloro pyridyl moiety were readily prepared in high yields via one-pot multicomponent reaction catalyzed by piperidine. This present protocol provides an efficient synthetic route to the target compounds with the characteristics of short reaction time, high yield, and easy separation of the products. (C) 2010 Elsevier Ltd. All rights reserved.
• Designing Tetrahydroimidazo[1,2-<i>a</i>]pyridine Derivatives via Catalyst-free Aza-Diels−Alder Reaction (ADAR) and Their Insecticidal Evaluation
  作者：Wenwen Zhang、Yinbo Chen、Weidong Chen、Zewen Liu、Zhong Li

  DOI：10.1021/jf100645y

  日期：2010.5.26

  A series of tetrahydroimidazo[1,2-a]pyridine derivatives were synthesized by the reaction of 2-vinyl-4,5-dihydroimidazole derivatives with substituted benzylidenemalononitrile via a catalyst-free aza-Diels-Alder reaction. Insecticidal activities of target compounds were tested against pea aphids (Aphis craccivora), which showed that activities were strongly influenced by the substituents and their positions. Especially, the introduction of a fluoro group at the 2- position increased activities.