2-(3-dimethylamino-1-phenyl-2-propenylidene)-1,3-propanedinitrile | 124571-67-1

• 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-dimethylamino-1-phenyl-2-propenylidene)-1,3-propanedinitrile
• 英文别名: 2-cyano-5-dimethylamino-3-phenyl-2,4-pentadienonitrile；(E)-2-(3-(dimethylamino)-1-phenylallylidene)malononitrile；2-[(E)-3-(dimethylamino)-1-phenylprop-2-enylidene]propanedinitrile
• CAS: 124571-67-1
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: DHIFGWUOTOJHEN-CMDGGOBGSA-N

物化性质

• 熔点：
  142-144 °C
• 沸点：
  317.1±42.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-dimethylamino-1-phenyl-2-propenylidene)-1,3-propanedinitrile 在 氢溴酸 作用下， 以 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 4-phenylpyridine-2,3-dicarbonitrile
  参考文献：
  名称：

  Prager, Rolf H.; Tsopelas, Chris; Heisler, Teresa, Australian Journal of Chemistry, 1991, vol. 44, # 2, p. 277 - 285

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(1-苯基亚乙基)丙二腈 在 potassium tert-butylate 作用下， 以 乙醚 、 叔丁醇 为溶剂， 反应 3.0h， 生成 2-(3-dimethylamino-1-phenyl-2-propenylidene)-1,3-propanedinitrile
  参考文献：
  名称：

  Reaction between 2-Phenyl-1,1-dicyanoallyl Anion and N-Methyl-2,2-dimethylpropionitrilium and N1,N2,N2-Trimethyl-2,2-dimethylpropionylamidinium Trifluoromethanesulfonates.

  摘要：

  The reaction of 2-phenyl-1,1-dicyanoallyl anion with N-methyl-2,2-dimethyl-propionitrilium ion (2) in acetonitrile solution resulted in formation of [3-(N-methylamino)-4,4-dimethyl-1-phenyl-2-pentenylidene]propanedinitrile (6), which at elevated temperature (25-50 degrees C, depending on the solvent) undergoes a ring closure to 2-(N-methylamino)-3-cyano-4-phenyl-6-tert-butylpyridine (7) or in the presence of aqueous acid to 3-cyano-4-phenyl-6-tert-butyl-2-pyrone (8). Using N,N-dimethylformamide as solvent, in addition to 7, two other compounds are formed, viz. (3-(N,N-dimethylamino)-1-phenyl-2-propenylidene)propanedinitrile (9) and N-(4,4-dicyano-3-phenyl-1, 3-butadienyl)-N,2,2-trimethylpropanamide (10). The latter two compounds are results of a primary reaction of the title nitrilium ion with the solvent to give N-1,N-2,N-2-trimethyl-N-1-2,2-dimethyl-propionylamidinium trifluoromethanesulfonate (11) which in turn reacted with the title allyl anion 2 to give 9 and 10, for which X-ray crystal structures were determined. Strong indications of a tetrahedral mechanism in the reaction of 2 with 11 are presented.

  DOI：

  10.3891/acta.chem.scand.50-0623

文献信息

• Gas-phase pyrolysis of 2-heteroaromatic-1-dimethylaminoethylenes: Kinetic and mechanistic study
  作者：Mohamed H. Elnagdi、Nouria A. Al-Awadi、Agith Kumar、Mervat Abdul Khalik

  DOI：10.1002/1098-1071(2001)12:1<47::aid-hc10>3.0.co;2-q

  日期：——

  onitrile (7) (Scheme 1) have been carried out. The rates of gas-phase pyrolytic reactions of compounds 3, 4, 5, and 7 have been measured and found to correspond to unimolecular first-order reactions. Product analyses together with kinetic data were used to outline a feasible pathway for the pyrolytic reactions of the compounds under study. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:47–51, 2001

  4(2'-二甲氨基乙烯基)-2-oxo-2H-benzo[b]pyran-3-carbonitrile (1), 4(2'-二甲氨基乙烯基)-2-oxo-2H-naphtho[1]的气相热解反应,2-b]pyran-3-carbonitrile (2), 1,6-dihydro-4-(2'-dimethylaminoethenyl)-6-oxo-1-phenylpyridazine-3,5-dicarbonitrile (3), 2-cyano- 5-二甲氨基-3-苯基-2,4-戊二烯腈(4), 2-氰基-5-二甲氨基-3-(2-噻吩基)-2,4-戊二烯腈(5), 1,2-二氢-4- (2'-二甲氨基乙烯基)-oxo-quinoline-4-carbonitrile (6), 6-(ethylthio)-4-(2'-dimethylaminoethenyl)-2-phenylpyrimidine-5-carbonitrile
• Solventless convenient synthesis of new cyano-2-aminopyridine derivatives from enaminonitriles
  作者：Didier Villemin、Zahira Belhadj、Nawel Cheikh、Noureddine Choukchou-Braham、Nathalie Bar、Jean-François Lohier

  DOI：10.1016/j.tetlet.2013.01.021

  日期：2013.3

  A synthesis of novel 4-substituted-3-cyano-2-aminopyridines using enaminonitriles and various primary amines was established under microwave irradiation and solvent-free conditions. Structures of the new compounds were characterized by IR, MS, 1H and 13C NMR data and the structure of 2-aminopyridine of the products was confirmed by X-ray analysis.

  在微波辐射和无溶剂条件下，使用烯胺腈和各种伯胺合成了新型的4-取代的-3-氰基-2-氨基吡啶。通过IR，MS，1 H和13 C NMR数据表征了新化合物的结构，并且通过X射线分析证实了产物的2-氨基吡啶的结构。
• Increasing Scope of Clickable Fluorophores: Electrophilic Substitution of Ylidenemalononitriles
  作者：Juliana M. de Souza、Irini Abdiaj、Jiaqi Chen、Kenneth Hanson、Kleber T. de Oliveira、D. Tyler McQuade

  DOI：10.1021/acs.joc.0c01551

  日期：2020.9.18

  access to more functionalized and polar-solvent-soluble structures as well as increased control over the rate of cyclization. Herein, we report a new approach that allows the electrophilic substitution of YMs. These substituted YMs exhibit faster turn-on rates, color tunability, access to polar-solvent-soluble species, and increased control over cyclization rate. This allowed us to significantly expand

  最近，我们证明了亚甲基丙二腈（YMs）与胺反应形成环状am，并且在溶液中起始的线性YM是无价的，环状and是荧光的。这些开启系统对我们很感兴趣，因为它们有潜力用作访问功能化吡啶的生物传感器和合成子。尽管我们最初的方法很有希望，但仍然存在一些局限性，包括获得功能更强且极性溶剂可溶的结构，以及对环化速率的控制增加。在此，我们报告了一种允许YMs亲电取代的新方法。这些取代的YM表现出更快的开启速度，颜色可调性，可溶于极性溶剂的种类以及对环化速率的增强控制。
• Studies With Functionally Substituted Heteroaromatics: A Novel Route for the Synthesis of 1-Aryl-6-oxopyridazinones, 1-Arylpyridazine-6-imines and 1-Aryl-6-imino-4-pyridazinals
  作者：Fatima Al-Omran、Mervat Mohammed Abdel Khalik、Adel Abou-Elkhair、Mohammed Hilmy Elnagdi

  DOI：10.1055/s-1997-1512

  日期：1997.1

  Aryldiazonium salts couple with the 3-dimethylamino-1-substituted enones 1 a-c to yield 2-arylhydrazono-3-oxo-3-substituted-propanals which are excellent precursors for the synthesis of pyridazinones. The coupling reaction of 2-cyano-5-dimethylamino-3-substituted-penta-2,4-dienonitrile 12 a-b with benzene diazonium salts in ethanolic sodium hydroxide gives the pyridazinals 13 a, b.

  Aryldiazonium 盐与3-二甲基氨基-1-取代烯酮 1 a-c 反应，生成2-芳基肼佐-3-氧代-3-取代丙醛，这些化合物是合成吡嗪酮的优秀前体。2-氰基-5-二甲基氨基-3-取代戊-2,4-二烯腈 12 a-b 与苯二氮盐在乙醇钠氢氧化物中反应，生成吡嗪醛 13 a, b。
• Al-Omran, Fatima; Al-Awadhi, Nouria; Khalik, Mervat Mohammed Abdel, Journal of Chemical Research, Miniprint, 1997, # 3, p. 601 - 615
  作者：Al-Omran, Fatima、Al-Awadhi, Nouria、Khalik, Mervat Mohammed Abdel、Kaul, Kamini、EL-Khair, Adel Abu、Elnagdi, Mohammed Hilmy

  DOI：——

  日期：——