6-Dicyanomethylene-2-methyl-2,4-bis(thien-2-yl)-1,2,3,6-tetrahydropyridine-5-carbonitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-Dicyanomethylene-2-methyl-2,4-bis(thien-2-yl)-1,2,3,6-tetrahydropyridine-5-carbonitrile
• 英文别名: 2-(5-cyano-2-methyl-2,4-dithiophen-2-yl-1,3-dihydropyridin-6-ylidene)propanedinitrile
• 化学式: C₁₈H₁₂N₄S₂
• 分子量: 348.452
• InChiKey: HLKANFKOOWUNDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-氯苯硫酚 、 6-Dicyanomethylene-2-methyl-2,4-bis(thien-2-yl)-1,2,3,6-tetrahydropyridine-5-carbonitrile 以 水 为溶剂， 反应 1.0h， 以454 mg的产率得到7-(3-chlorophenylthio)-5-amino-1,2-dihydro-2-methyl-2,4-di(thiophen-2-yl)-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-乙酰基噻吩 、 丙二腈 在 盐酸 、 (Me₂NH)n*CO₂ 作用下， 生成 6-Dicyanomethylene-2-methyl-2,4-bis(thien-2-yl)-1,2,3,6-tetrahydropyridine-5-carbonitrile
  参考文献：
  名称：

  Synthese von cyanosubstiuierten Di- und Tetrahydropyridinen in DIMCARB (Dimethylamin-CO2-Additionsverbindung)

  摘要：

  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.

  DOI：

  10.1002/prac.19973390173

文献信息

• Pseudo-Five-Component Domino Strategy for the Combinatorial Library Synthesis of [1,6] Naphthyridines—An On-Water Approach
  作者：Paramita Das、Tandrima Chaudhuri、Chhanda Mukhopadhyay

  DOI：10.1021/co400162m

  日期：2014.11.10

  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.
• 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.