2-[3-cyano-4,6-bis-(4-chlorophenyl)-6-methyl-5,6-dihydropyridin-2(1H)-ylidene]-malononitrile | 106000-65-1

• 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-[3-cyano-4,6-bis-(4-chlorophenyl)-6-methyl-5,6-dihydropyridin-2(1H)-ylidene]-malononitrile
• 英文别名: 2,4-Bis(p-chlorphenyl)-5-cyano-6-dicyanomethylen-2-methyl-1,2,3,6-tetrahydropyridin；2-[2,4-Bis(4-chlorophenyl)-5-cyano-2-methyl-1,3-dihydropyridin-6-ylidene]propanedinitrile
• CAS: 106000-65-1
• 化学式: C₂₂H₁₄Cl₂N₄
• 分子量: 405.286
• InChiKey: RNXGXBOKBXDQKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氯苯硫酚 、 2-[3-cyano-4,6-bis-(4-chlorophenyl)-6-methyl-5,6-dihydropyridin-2(1H)-ylidene]-malononitrile 以 水 为溶剂， 反应 1.0h， 以506 mg的产率得到7-(3-chlorophenylthio)-5-amino-2,4-bis(4-chlorophenyl)-1,2-dihydro-2-methyl-1,6-naphthyridine-8-carbonitrile
  参考文献：
  名称：

  Pseudo-Five-Component Domino Strategy for the Combinatorial Library Synthesis of [1,6] Naphthyridines—An On-Water Approach

  摘要：

  This work features the base-promoted on-water synthesis of [1,6]-naphthyridines from methyl ketones, malononitrile and phenols or thiols. The reaction conditions were carefully tuned to drive the product selectivity from 3H-pyrroles to [1,6]-naphthyridines. The advantages of this method lie in its simplicity, cost effectiveness, and environmental friendliness, representing a new effort toward the on-water synthesis of [1,6]-naphthyridines without starting from a nitrogen-containing heterocycle and highlighting the versatility of the nitrile functional group.

  DOI：

  10.1021/co400162m
• 作为产物：
  描述：

  2-[1-(4-氯苯基)亚乙基]丙二腈 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以97%的产率得到2-[3-cyano-4,6-bis-(4-chlorophenyl)-6-methyl-5,6-dihydropyridin-2(1H)-ylidene]-malononitrile
  参考文献：
  名称：

  一些新型的聚氮杂稠合杂环化合物的合成

  摘要：

  2-（1-芳基-亚乙基）-丙二腈1a，1b，1c，1d在乙醇中由乙醇钠催化进行自二聚反应，得到2- [4,6-二芳基-3-氰基-6-甲基-5,6-二氢吡啶-2（1 H）-亚烷基]-丙二腈衍生物3a，3b，3c，3d。X射线晶体学阐明了二聚体的结构，并描述了其形成的合理机理。化合物3a与芳烃重氮盐4a，4b，4c，4d偶联，得到肼衍生物5a，5b，5c，5d并与水合肼和苯肼6a，6b反应，得到吡唑并[3,4-h] [1,6]萘啶衍生物7a，7b，并与尿素和硫脲8a，8b反应得到嘧啶基[4,5-h] [1,6]萘啶衍生物9a，9b。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.329

文献信息

• Regioselective [5 + 1] rearrangement–annulation: a new and efficient domino route to highly functionalized [1,6]naphthyridines
  作者：Man-Su Tu、Ying Li、Xiang Wang、Bo Jiang、Shu-Liang Wang、Shu-Jiang Tu

  DOI：10.1039/c3ra22328k

  日期：——

  A new [5 + 1] rearrangement–annulation for the regioselective formation of polyfunctionalized [1,6]naphthyridines is described. The new construction of a pyridin-2(1H)-one skeleton and its alkylation on the pyridin-2(1H)-one unit were readily achieved through a novel sequential [4 + 2] cyclization–ring opening–intramolecular cyclization–re-cyclization–elimination of urea process.

  描述了一种新的 [5 + 1] 重新排列-环化反应，用于区域选择性生成多功能化的 [1,6] 萘啶。通过一种新颖的顺序 [4 + 2] 环化-开环-分子内环化-再环化-尿素消除过程，成功构建了吡啶-2(1H)-酮骨架及其在吡啶-2(1H)-酮单元上的烷基化。
• Abramenko, Yu. T.; Ivashchenko, A. V.; Nogaeva, K. A., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 230 - 235
  作者：Abramenko, Yu. T.、Ivashchenko, A. V.、Nogaeva, K. A.、Andronova, N. A.、Putsykina, E. B.

  DOI：——

  日期：——
• Synthese von cyanosubstiuierten Di- und Tetrahydropyridinen in DIMCARB (Dimethylamin-CO2-Additionsverbindung)
  作者：S. Dunkel、U. Heß、G. Reck

  DOI：10.1002/prac.19973390173

  日期：——

  A new selective method for base-catalyzed ring closure reaction of acetophenones (1a-1) with malononitrile in DIMCARB (dimethylamine-CO2-addition-compound) as solvent of high dimethylamine concentration is reported which allows effective syntheses of (1.2-dihydro-4-pyrid-6-yl)dicyanomethanides and 5-cyano-6-dicyanomethylene-1,2,3,6-tetrahydropyridines in good yields, The structure of the two new classes of compounds is proved by X-ray diffraction analysis.