2-Cyano-5-dimethylamino-penta-2,4-diensaeurenitril | 1508-12-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Cyano-5-dimethylamino-penta-2,4-diensaeurenitril
• 英文别名: (3-dimethylaminoprop-2-enylidene)malononitrile；1,1-dicyano-4-dimethylaminobuta-1,3-dien；1,1-dicyano-4-N,N-dimethylamino-1,3-butadiene；4-Dimethylamino-buta-1,3-dien-1,1-dicarbonsaeure-dinitril；4-Dimethylamino-1,3-butadien-1,1-dicarbonitril；4-Dimethylamino-1,1-dicyan-butadien-(1,3)；[3-(Dimethylamino)prop-2-en-1-ylidene]propanedinitrile；2-[3-(dimethylamino)prop-2-enylidene]propanedinitrile
• CAS: 1508-12-9
• 化学式: C₈H₉N₃
• 分子量: 147.18
• InChiKey: COMHXTNMJANPSM-UHFFFAOYSA-N

物化性质

• 熔点：
  130-134 °C
• 沸点：
  240.3±30.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 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-Cyano-5-dimethylamino-penta-2,4-diensaeurenitril 、 氨 在 乙醇 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以12.7 parts (91% of theory) of 2-aminonicotine nitrile, of melting point 130° to 132° C. (from ethanol), are obtained的产率得到2-氨基-3-氰基吡啶
  参考文献：
  名称：

  Preparation of butadiene dinitriles

  摘要：

  丁二腈是通过在烷醇存在下，将季铵化合物与马洛二腈反应，然后将产物与碱金属化合物反应制备的。本发明所得的丁二腈是制备染料、杀虫剂、药物和维生素的有价值的起始材料。

  公开号：

  US04410465A1
• 作为产物：
  描述：

  N,N-(3-chloro-3-methoxy-propylidene)-N,N-dimethylammonium chloride 以 甲醇 为溶剂， 生成 2-Cyano-5-dimethylamino-penta-2,4-diensaeurenitril
  参考文献：
  名称：

  Preparation of butadiene dinitriles

  摘要：

  丁二腈是通过将季铵化合物与马乐腈在烷醇存在下反应，然后再将产物与碱金属化合物反应制备的。本发明所得到的丁二腈是制备染料、杀虫剂、药物和维生素的有价值的起始物质。

  公开号：

  US04410465A1

文献信息

• Reactions of 2,2-disubstituted 1,1-dicyanoethenes with β-dimethylaminoacrolein aminal and 3-dimethylamino-1,1,3-trimethoxypropane
  作者：Zh. A. Krasnaya、E. O. Tret’yakova、V. V. Kachala、S. G. Zlotin

  DOI：10.1007/s11172-008-0219-0

  日期：2008.8

  A reaction of 2,2-disubstituted 1,1-dicyanoethenes with β-dimethylaminoacrolein aminal and 3-dimethylamino-1,1,3-trimethoxypropane leads to substituted 6,6-dicyano-1-dimethyl-aminohexatrienes and an organic salt containing 1,1,9,9-tetracyano-2,8-diphenylnona-2,4,6,8-tetraenide as the anion and (dimethylaminopropenylidene)dimethylammonium as the cation, on the basis of which new cation-anionic polymethine dyes were obtained.

  2,2-二取代的 1,1-二氰基乙烯与 β-二甲基氨基丙烯醛氨基和 3-二甲基氨基-1,1,3-三甲氧基丙烷反应，生成取代的 6,6-二氰基-1-二甲基氨基己三烯和含有 1、1,9,9-tetracyano-2,8-diphenylnona-2,4,6,8-tetraenide 作为阴离子，(dimethylaminopropenylidene)dimethylammonium 作为阳离子的有机盐。
• 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.
• Bredereck,H. et al., Chemische Berichte, 1970, vol. 103, p. 222 - 235
  作者：Bredereck,H. et al.

  DOI：——

  日期：——
• Reaction of ?-dimethylaminoacrolein aminal with alcohols and CH-acids
  作者：Zh. A. Krasnaya、T. S. Stytsenko

  DOI：10.1007/bf00955292

  日期：1981.5