ethyl 2-cyano-5-dimethylamino-3-phenylpenta-2,4-dienoate | 87853-63-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 2-cyano-5-dimethylamino-3-phenylpenta-2,4-dienoate
• 英文别名: ethyl 2-cyano-5-(dimethylamino)-3-phenylpenta-2,4-dienoate
• CAS: 87853-63-2
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: QWFSNSMTAIGYCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyano-5-dimethylamino-3-phenylpenta-2,4-dienoate 在 溶剂黄146 作用下， 反应 3.0h， 以87%的产率得到ethyl 2-oxo-4-phenyl-1,2-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Duong, Thach; Prager, Rolf H.; Were, Stephen T., Australian Journal of Chemistry, 1983, vol. 36, # 7, p. 1431 - 1440

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-2-cyano-3-phenylbut-2-enoic acid ethyl ester 、 N,N-二甲基甲酰胺二甲基缩醛 反应 3.0h， 以93%的产率得到ethyl 2-cyano-5-dimethylamino-3-phenylpenta-2,4-dienoate
  参考文献：
  名称：

  Duong, Thach; Prager, Rolf H.; Were, Stephen T., Australian Journal of Chemistry, 1983, vol. 36, # 7, p. 1431 - 1440

  摘要：

  DOI：

文献信息

• Novel bis-(3-cyano-2-pyridones) derivatives: synthesis and fluorescent properties
  作者：Nawel Mehiaoui、Zahira Kibou、Thibault Gallavardin、Stéphane Leleu、Xavier Franck、Ricardo F. Mendes、Filipe A. Almeida Paz、Artur M. S. Silva、Noureddine Choukchou-Braham

  DOI：10.1007/s11164-020-04373-8

  日期：2021.4

  Abstract Novel substituted bis-(3-cyano-2-pyridone) derivatives were prepared via a powerful method using enaminonitriles push–pull dienes as key building blocks. The synthesis was performed in three steps from easily accessible starting materials in good yields. All target products were structurally elucidated by spectroscopic data. The reaction mechanism for formation of bis (3-cyano-2-pyridone)

  摘要 新型取代的双（3-氰基-2-吡啶酮）衍生物是通过强大的方法制备的，使用烯腈腈推挽二烯作为关键构件。从容易获得的起始原料以高收率分三步进行合成。通过光谱数据在结构上阐明了所有目标产物。提出了形成双（3-氰基-2-吡啶酮）衍生物的反应机理。通过单晶X射线衍射确认了烯胺腈3a和双吡啶酮4c的结构。据报道一些双（3-氰基-2-吡啶酮）衍生物的荧光研究。 图形概要
• Orthoamide. L. Beiträge zur Chemie von Propiolaldehydaminalen - Synthesen und Umsetzungen zu Push-Pull-substituierten Buta-1,3-dienen, Cyclobutanen sowie vinylogen Amidiniumsalzen und 1,2,3-Triazolen
  作者：Michael Kiesel、Erwin Haug、Willi Kantlehner

  DOI：10.1002/prac.19973390130

  日期：——

  Tert-butylaminalester 5 reacts with terminal alkynes to give aminals of substituted propiolaldehydes 3c,d. The aminal 3a is accessible from N,N,N,N'-tetramethylformamidinium chloride (7b) and sodium acetylide. The aminals 3b,c can also be prepared from bis(dimethylamino)acetonitrile 8 and terminal alkynes in the presence of sodium hydride. The nitrile 8 is also useful for the preparation of the bis-aminal of acetylenedialdehyde 6. The aminal 3e can be transaminated by heating with secondary amines to give the aminals 3f-i. The aminals 3a-i react with strong CH2-acidic compounds (pK(a) between 9 and 14) to give the 1-dialkylamino-1,3-butadienes 10. The isomeric 1-dialkylamino-butadienes 18 can be obtained from the condensation of the CH-acidic cinnamic acid derivatives 19 with dimethylformamidedimethylacetal. CH and NH-acidic compounds as cyanacetamide react with the aminals 3c,e exclusively with the acidic methylene group to produce the enamines 10h,t. The acylformamidine 21 can be obtained from 10t and tert-butylaminalester 5. The pyridone 22 is accessible from the condensation product 10h by thermal cyclization. The pyrido[2,3-d]pyrimidine 26 is formed in the reaction of the 6-amino-uracile 23 with the aminal 3a. In an unexpected reaction the 1,2-bis(cyano-dialkylaminomethylene)-cyclobutanes 28a-d result from the action of trimethylsilylcyanide on the aminals 3e-h. The corresponding reaction with trimethylsilylisothiocyanate affords the vinylogous amidinium thiocyanates 34a,b. In the reaction of trimethylsilylazide and the aminals 3 are produced the 4-(dialkylaminomethylene)-4H-1,2,3-triazoles 38.