dibutyl (E)-2,3-dicyanobutendioate | 131534-48-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dibutyl (E)-2,3-dicyanobutendioate
• 英文别名: dibutyl (E)-2,3-dicyanobut-2-enedioate
• CAS: 131534-48-0
• 化学式: C₁₄H₁₈N₂O₄
• 分子量: 278.308
• InChiKey: JIGIBENBKCSBOB-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dibutyl (E)-2,3-dicyanobutendioate 在 盐酸 、 sodium azide 、 sodium acetate 、 sodium nitrite 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 6.42h， 生成 2-Amino-5-cyano-6-oxo-1,6-dihydro-pyridine-3,4-dicarboxylic acid dibutyl ester
  参考文献：
  名称：

  A Novel Synthesis of 1,6-Diamino-2-pyridones and [1,2,4]Triazolo-[1,5-a]pyridine Derivatives

  摘要：

  3-Cyano-1,6-diamino-2-pyridone derivatives (3) possessing various alkoxycarbonyl groups are prepared directly from the reaction of dialkyl (E)-2,3-dicyanobutendioates (1) with cyano-acetohydrazide (2). The resulting diamine (3) (R = Et) is readily cyclized to 8-substituted [1,2,4]triazolo[1,5-a]pyridine derivatives (5) in high yields by treatment with orthocarboxylic esters (4) such as trimethyl orthoformate or triethyl orthoacetate etc. Furthermore, 3-cyano-6-amino-2-pyridones (6) are although obtained in excellent yields by the reductive deamination of 3. The structural study of 6 was carried out by spectroscopic methods in some details.

  DOI：

  10.3987/com-98-8136
• 作为产物：
  描述：

  氰乙酸正丁酯 在 水 、 溴 、 potassium thioacyanate 作用下， 以 四氯化碳 为溶剂， 反应 1.58h， 生成 dibutyl (E)-2,3-dicyanobutendioate
  参考文献：
  名称：

  A Convenient Synthesis of Dialkyl (E)-2,3-Dicyanobutendioates

  摘要：

  4，二烷基（E）-2,3-二氰基丁二烯二酯是一类可能有用且能合成多种杂环化合物中间体的化合物，可通过二烷基溴氰基乙酸酯2与硫氰酸钾在乙腈中的反应，然后用水处理而方便地制备。起始原料二烷基溴氰基乙酸酯则是通过适当二烷基氰基乙酸酯与四氯化碳中的溴进行光化学反应制备得到的。

  DOI：

  10.1055/s-1990-27009

文献信息

• A convenient synthesis of (z)-3-(α-alkoxycarbonyl-α-cyanomethylene)-2-oxo-1,2,3,4-tetrahydroquinoxalines and related compounds
  作者：Yoichi Yamada、Heinosuke Yasuda

  DOI：10.1002/jhet.5570350628

  日期：1998.11

  (Z)-3-(α-Alkoxycarbonyl-α-cyanomethylene)-2-oxo-1,2,3,4-tetrahydroquinoxalines 3 and (Z)-3-(α-alkoxycarbonyl-α-cyanomethylene)-3,4-dihydrobenzo[g]quinoxalin-2(1H)-ones 5 possessing various alkoxycarbonyl groups were prepared in good yields directly from the reaction of dialkyl (E)-2,3-dicyanobutendioates 1 with o-phenylenediamine (2) or with 2,3-diaminonaphthalene (4), respectively. Furthermore, 2

  （Z）-3-（α-烷氧羰基-α-氰基亚甲基）-2-氧-1,2,3,4-四氢喹喔啉3和（Z）-3-（α-烷氧羰基-α-氰基亚甲基）-3,4直接由二烷基（E）-2,3-二氰基丁二酸酯1与邻苯二胺（2）或2的反应以高收率制备具有各种烷氧羰基的-dihydrobenzo [ g ] quinoxalin-2（1 H）-ones 5分别为，3-二氨基萘（4）。此外，使2，3-二氨基吡啶（6）和3，4-二氨基吡啶（7）与二乙酯1b反应。得到（Z）-2-（α-氰基-α-乙氧基羰基亚甲基）-1,2-二氢-4 H-吡啶并[2,3 - b ]吡嗪-3-一（8）和（Z）-3- （α-氰基-α-乙氧基羰基亚甲基）-3，4-二氢-1 H-吡啶并[3，4- b ]吡嗪-2-酮（9）。的结构研究3，5，8，和9通过在一些细节NMR实验进行。
• Influence of Lewis Acids on the Cycloaddition Reactions of Cyano- and Carbomethoxy-Substituted Olefins
  作者：Warunee Srisiri、Anne Buyle Padias、H. K. Hall

  DOI：10.1021/jo00097a054

  日期：1994.9

  The reactions of electrophilic olefins substituted with cyano and/or carbomethoxy groups with donor olefins are investigated. The donor olefins include, in order of decreasing donor character, phenyl vinyl sulfide, isobutyl vinyl ether, tert-butyldimethylsilyl vinyl ether, p-methoxy- and p-methylstyrene, and styrene. The reactions vary ii om [2 + 2] cycloadditions to Diels-Alder reactions to spontaneous free radical copolymerizations. The course of the reaction is determined by both the electron disparity between the two reacting olefins and by the substitution pattern on the electrophilic olefin. Lewis acids (ZnCl2 or ethereal LiClO4) are added to form complexes with the acceptor olefins, resulting in a larger electron disparity between the reactants. With the highly electrophilic olefins with gem-dicyano groups, such as tetracyanoethylene, dimethyl 1,1-dicyanoethylene-2,2-dicarboxylate, and methyl beta,beta-dicyanoacrylate, [2 + 2] cycloadditions occur at room temperature, except for the reaction of TCNE with styrene which has to be carried out in 5 M ethereal LiClO4. With olefins containing one cyano and one carbomethoxy group on the same carbon, dimethyl dicyanofumarate and dimethyl cyanofumarate, inverse electron demand Diels-Alder cycloaddition involving the ester substituent dominates in reactions with the most nucleophilic olefins. The [2 + 2] cycloadducts can be obtained in the presence of Lewis acid. With olefins with two carbomethoxy-substituents on the same carbon, dimethyl 2-cyanoethene-1,1-dicarboxylate and trimethyl ethylenetricarboxylate, the reactions are much slower, and [2 + 4] cycloaddition dominates with the most reactive donor olefins, while the [2 + 2] cycloadduct can be obtained in the presence of Lewis acid. With several acceptor olefins, free radical copolymerizations compete with the cycloadditions when reacted with the least reactive donor olefins. The reaction tendencies are discussed in light of the electron disparity between the olefins. The influence of the Lewis acid on the conformational equilibria and on the reaction course is also addressed.
• A Convenient Synthesis of (Z)-3- (a-Cyano-a-alkoxycarbonylmethylene)-2-piperazinones and Their Derivatives
  作者：Yoichi Yamada、Heinosuke Yasuda、Masaaki Kasai

  DOI：10.3987/com-99-8645

  日期：——

  (Z)-3-(alpha-Cyano-alpha-alkoxycarbonylmethylene)-2-piperazinone derivatives (3) and trans-(Z)-3-(alpha-cyano-alpha-alkoxycarbonylmethylene)-octahydro-2 (1H)-quinoxalinone derivatives (5) possessing various alkoxycarbonyl groups are prepared directly from the reaction of dialkyl (E)-2,3-dicyanobutenedioates (1) with ethylenediamine (2) and with trans-1,2-diaminocyclohexane (4), respectively. Furthermore, cis-1,2-diaminocycloheptane (6) and meso-2,3-diaminobutane (8) were reacted with the diethyl ester Ib to give cis-(Z)-3-(alpha-cyano-alpha-ethoxycarbonyl-methylene)decahydro-2H-cycloheptapyrazin-2-one (7) and cis-(Z)-3-(alpha-cyanoyano-alpha-ethoxycarbonylmethylene)-5,6-dimethyl-2-piperazinone (9), respectively. The structural studies of 3, 5, 7, and 9 were carried out by NMR experiments in some details.
• A Simple Synthesis of 1-Substituted 5-Aminopyrazoles and Pyrazolo[1,5-a]-s-triazine Derivative
  作者：Yoichi Yamada、Heinosuke Yasuda、Kazue Yoshizawa

  DOI：10.3987/com-98-8262

  日期：——

  Dialkyl 5-amino-1-carbamoylpyrazole-3,4-dicarboxylates (3) and the l-aryl derivatives (5) are synthesized directly by the reaction of semicarbazide (2) or arylhydrazines (4) with dialkyl (E)-2,3-dicyanobutendioates (1) in the presence of organic salts, such as ammonium acetate or sodium acetate. Furthermore, the reaction of the 1,3-diamino compound (3; R= Et) with trimethyl orthoformate in acetic acid led to the formation of diethyl 7-hydroxypyrazolo[1,5-a]-s-triazine-2,3-dicarboxylate (6).
• YAMADA, YOICHI;YASUDA, HEINOSUKE, SYNTHESIS (BRD),(1990) N, C. 768-770
  作者：YAMADA, YOICHI、YASUDA, HEINOSUKE

  DOI：——

  日期：——