2-Cyano-5-dimethylamino-5-phenyl-penta-2,4-diensaeureamid | 54818-68-7

• 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-Cyano-5-dimethylamino-5-phenyl-penta-2,4-diensaeureamid
• 英文别名: 2-cyano-5-(dimethylamine)-5-phenylpenta-2,4-dienamide；2-cyano-5-(dimethylamino)-5-phenylpenta-2,4-dienamide；2-cyano-5-dimethylamino-5-phenylpenta-2,4-dienoic acid amide；2-Cyano-5-(dimethylamino)-5-phenylpenta-2,4-dienamide
• CAS: 54818-68-7
• 化学式: C₁₄H₁₅N₃O
• 分子量: 241.293
• InChiKey: SQVPRZPJMZLJCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Cyano-5-dimethylamino-5-phenyl-penta-2,4-diensaeureamid 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以89%的产率得到2-氧代-6-苯基-1,2-二氢-3-吡啶羧酸
  参考文献：
  名称：

  Enaminones 作为杂环合成中的构件：重新研究 Enaminones 与丙二腈的产品结构。6-Substituted-3-Oxo-2,3-Dihydropyridazine-4-Carboxylic Acids 的新途径

  摘要：

  对烯胺酮与丙二腈在乙醇哌啶中反应产物的结构进行了修订。通过 2-cyano-5-(二甲氨基)-5-arylpenta-2,4-dienamides 8a-c 与亚硝酸或与重氮苯氯化物反应获得 2,3-二氢哒嗪-4-羧酸 4a-c 的新途径是报道。化合物8a-c在EtOH/HCl和AcOH中回流时转化为1,2-二氢吡啶-3-羧酸和1,2-二氢吡啶-3-甲腈衍生物。

  DOI：

  10.3390/molecules14010068
• 作为产物：
  描述：

  3-chloro-3-phenyl-1-prop-2-en-1-yliden-dimethyliminium perchlorate 、 氰乙酰胺 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 2-Cyano-5-dimethylamino-5-phenyl-penta-2,4-diensaeureamid
  参考文献：
  名称：

  Liebscher,J.; Hartmann,H., Journal fur praktische Chemie (Leipzig 1954), 1976, vol. 318, # 5, p. 705 - 730

  摘要：

  DOI：

文献信息

• About the reaction of β-dimethylamino-α,β-enones with active methylene nitriles
  作者：Fathy M. Abdelrazek、Akram N. Elsayed

  DOI：10.1002/jhet.181

  日期：2009.9

  The reaction of 3-dimethylamino-1-arylpropenone derivatives with active methylene nitriles was reinvestigated and a plausible mechanism to account for the results is suggested. X-ray crystallographic study supported the suggested mechanism. Based on these findings, the reaction of 3-acetylamino-4-dimethylaminobut-3-en-2-one with malononitrile was also reinvestigated and the correct structures verified

  对3-二甲基氨基-1-芳基丙烯酮衍生物与活性亚甲基腈的反应进行了重新研究，并提出了一种可能的机制来解释这一结果。X射线晶体学研究支持所提出的机理。根据这些发现，3-乙酰氨基-4-二甲基氨基丁-3-en-2-one与还对丙二腈进行了重新研究，并验证了正确的结构。J.杂环化​​学，（2009）。
• Chitosan Based Heterogeneous Catalyses: Chitosan-Grafted-Poly(4-Vinylpyridne) as an Efficient Catalyst for Michael Additions and Alkylpyridazinyl Carbonitrile Oxidation
  作者：Khaled Khalil、Hamad Al-Matar

  DOI：10.3390/molecules18055288

  日期：——

  be synthesized under heterogeneous conditions in presence of a potassium persulfate and sodium sulfite redox system. The synthesized graft copolymer could be utilized effectively, in the form of beads, as an efficient catalyst for Michael additions of active methylenes to functionally substituted alkenes. Moreover, methyl moiety oxidation in methyl pyridazinyl carbonitriles by H2O2 in the presence of

  壳聚糖接枝聚（4-乙烯基吡啶）（Cs-PVP）共聚物可以在过硫酸钾和亚硫酸钠氧化还原系统存在的非均相条件下合成。合成的接枝共聚物可以以珠的形式有效地用作活性亚甲基与官能取代烯烃的迈克尔加成反应的有效催化剂。此外，在壳聚糖-g-聚乙烯吡啶负载的铁 (III) 配合物 Cs-PVP/Fe 存在下，H2O2 对甲基哒嗪基腈中的甲基部分氧化可能会受到影响。在这些接枝共聚物珠的存在下，可以通过新的催化途径有效地合成各种吡喃、萘并吡喃和噻喃。这些聚合物催化剂可以用来代替旧的有毒的商业有机碱性催化剂，哌啶或吡啶，
• 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.
• Enaminones as Building Blocks in Heterocyclic Syntheses: Reinvestigating the Product Structures of Enaminones with Malononitrile. A Novel Route to 6-Substituted-3-Oxo-2,3-Dihydropyridazine-4-Carboxylic Acids
  作者：Abdul-Aziz Alnajjar、Mervat Mohammed Abdelkhalik、Amal Al-Enezi、Mohamed Hilmy Elnagdi

  DOI：10.3390/molecules14010068

  日期：——

  products of enaminones with malononitrile in ethanolic piperidine are revised. A novel route to 2,3-dihydropyridazine-4-carboxylic acids 4a-c via reactions of 2-cyano-5-(dimethylamino)-5-arylpenta-2,4-dienamides 8a-c with nitrous acid or with benzenediazonium chloride is reported. Compounds 8a-c are converted to 1,2-dihydropyridine-3-carboxylic acid and 1,2-dihydropyridine-3-carbonitrile derivatives upon

  对烯胺酮与丙二腈在乙醇哌啶中反应产物的结构进行了修订。通过 2-cyano-5-(二甲氨基)-5-arylpenta-2,4-dienamides 8a-c 与亚硝酸或与重氮苯氯化物反应获得 2,3-二氢哒嗪-4-羧酸 4a-c 的新途径是报道。化合物8a-c在EtOH/HCl和AcOH中回流时转化为1,2-二氢吡啶-3-羧酸和1,2-二氢吡啶-3-甲腈衍生物。
• Liebscher,J.; Hartmann,H., Journal fur praktische Chemie (Leipzig 1954), 1976, vol. 318, # 5, p. 705 - 730
  作者：Liebscher,J.、Hartmann,H.

  DOI：——

  日期：——