(E)-3-cyano-6,6-dimethyl-4-(4-nitrophenylvinyl)-5,6-dihydropyran-2-one | 255065-85-1

• 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: (E)-3-cyano-6,6-dimethyl-4-(4-nitrophenylvinyl)-5,6-dihydropyran-2-one
• 英文别名: 2,2-dimethyl-4-[(E)-2-(4-nitrophenyl)ethenyl]-6-oxo-3H-pyran-5-carbonitrile
• CAS: 255065-85-1
• 化学式: C₁₆H₁₄N₂O₄
• 分子量: 298.298
• InChiKey: REEGRPHBMPNITJ-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-cyano-6,6-dimethyl-4-(4-nitrophenylvinyl)-5,6-dihydropyran-2-one 反应 3.0h， 生成 (Z)-3-cyano-6,6-dimethyl-4-(4-nitrophenylvinyl)-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Synthesis and Photoisomerization of 3-Cyano-6,6-dimethyl-4-(4-nitrophenylvinyl)-5,6-dihydropyran-2-one

  摘要：

  DOI：

  10.1023/b:cohc.0000018335.49120.af
• 作为产物：
  描述：

  对硝基苯甲醛 、 4,6,6-trimethyl-2-oxo-5,6-dihydro-2H-pyran-3-carbonitrile 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.2h， 以61%的产率得到(E)-3-cyano-6,6-dimethyl-4-(4-nitrophenylvinyl)-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Vasodilating and antiarrhythmic activity of heteryl lactones

  摘要：

  A new series of unsaturated gamma- and delta-lactones with pyridyl, quinolyl and nitrophenyl substituents (9, 10) have been synthesized by the condensation of unsaturated methyl lactones with heteryl aldehyde or nitrobenzaldehyde in the base-catalysed aldol reaction. The antiarrhythmic, vasodilating and cardiotonic activities of the synthesized compounds have been studied in vivo and ex vivo. 3-Cyano-5,5-dimethyl-4-[4'-(4-pyridyl)-1',3'-butadienyl)]-2(5H)-furanone (9e) displayed a significant vasodilating activity. The antiarrhythmic activity of this compound was higher, but its toxicity lower than that of the procainamide reference drug. Five-membered lactones, particularly 3-cyano-4-(4-pyridylvinyl)-5,5-dimethyl-2(5H)-furanone (9c), exhibited a remarkable cardiotonic activity. The replacement of a pyridyl substituent by a nitrophenyl group in the pyranone derivative did not change the cardiovascular activity and toxicity. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00206-8

文献信息

• Vasodilating and antiarrhythmic activity of heteryl lactones
  作者：Ludmila Leite、Daina Jansone、Maris Veveris、Helena Cirule、Yuris Popelis、Gagik Melikyan、Anna Avetisyan、Edmunds Lukevics

  DOI：10.1016/s0223-5234(99)00206-8

  日期：1999.10

  A new series of unsaturated gamma- and delta-lactones with pyridyl, quinolyl and nitrophenyl substituents (9, 10) have been synthesized by the condensation of unsaturated methyl lactones with heteryl aldehyde or nitrobenzaldehyde in the base-catalysed aldol reaction. The antiarrhythmic, vasodilating and cardiotonic activities of the synthesized compounds have been studied in vivo and ex vivo. 3-Cyano-5,5-dimethyl-4-[4'-(4-pyridyl)-1',3'-butadienyl)]-2(5H)-furanone (9e) displayed a significant vasodilating activity. The antiarrhythmic activity of this compound was higher, but its toxicity lower than that of the procainamide reference drug. Five-membered lactones, particularly 3-cyano-4-(4-pyridylvinyl)-5,5-dimethyl-2(5H)-furanone (9c), exhibited a remarkable cardiotonic activity. The replacement of a pyridyl substituent by a nitrophenyl group in the pyranone derivative did not change the cardiovascular activity and toxicity. (C) 1999 Editions scientifiques et medicales Elsevier SAS.
• 10.1023/b:cohc.0000040766.10102.81
  作者：Leite、Jansone、Fleisher、Kazhoka、Popelis、Veretennikova、Shestakova、Domracheva、Lukevics

  DOI：10.1023/b:cohc.0000040766.10102.81

  日期：——
• Synthesis and Photoisomerization of 3-Cyano-6,6-dimethyl-4-(4-nitrophenylvinyl)-5,6-dihydropyran-2-one
  作者：D. Jansone、M. Fleisher、G. Andreeva、L. Leite、J. Popelis、E. Lukevics

  DOI：10.1023/b:cohc.0000018335.49120.af

  日期：2003.12