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
• Preparation of butadiene dinitriles
  申请人：BASF Aktiengesellschaft

  公开号：US04410465A1

  公开（公告）日：1983-10-18

  Butadiene dinitriles are prepared by reacting a quaternary ammonium compound with malodinitrile in the presence of an alkanol and then reacting the product with an alkali metal compound. The butadiene dinitriles obtainable by the process of the invention are valuable starting materials for the preparation of dyes, pesticides, drugs and vitamins.

  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。