dipropyl (E)-2,3-dicyanobutendioate | 131548-74-8

• 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: dipropyl (E)-2,3-dicyanobutendioate
• 英文别名: di-n-propyl dicyanofumarate；DnPrDCF；dipropyl (E)-2,3-dicyanobut-2-enedioate
• CAS: 131548-74-8
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: NNDIKVQRSDQZCS-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  dipropyl (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 dipropyl 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：

  氰乙酸正丙酯 在 水 、 溴 、 potassium thioacyanate 作用下， 以 四氯化碳 为溶剂， 反应 1.58h， 生成 dipropyl (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。
• 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).
• Structure–property correlations in a family of decamethylmetallocenium charge-transfer salt magnets using dialkyl dicyanofumarates as the one-electron acceptors: Ferromagnetism versus metamagnetism
  作者：William S. Tyree、Carla Slebodnick、Mary C. Spencer、Guangbin Wang、Joseph S. Merola、Gordon T. Yee

  DOI：10.1016/j.poly.2005.03.030

  日期：2005.11

  The synthesis of molecule-based magnets derived from decamethylchromocene, CrCp2*, and dialkyl dicyanofumarates, DRDCF, R = n-propyl (nPr) and isopropyl (iPr) yields two new members of a family of charge transfer (CT) salts, these being metamagnetic solids isomorphous with and reminiscent of the known diethyl (R = Et) homolog. The antiferromagnetic properties of these compounds contrast sharply with the previously reported ferromagnetic dimethyl (R = Me) compound. An examination of the four crystal structures provides an explanation for the observed behavior: although the pseudo-one-dimensional mixed stack structure is retained in all of the solids, a new relationship between the stacks is observed for the higher homologs that is different from that found for the DMeDCF salt. In the corresponding decamethylmanganocene, MnCp2*, family, CT salts with DnPrDCF and DiPrDCF are both metamagnets that appear to enter a spin glass state well below their T-N's, exhibiting hysteresis with large very coercivity at 1.8 K, again similar to behavior previously seen for the corresponding diethyl compound and different from the dimethyl compound. These and other results reported herein indicate that meaningful structure-property correlations are possible in this class of compounds. (c) 2005 Elsevier Ltd. All rights reserved.
• YAMADA, YOICHI;YASUDA, HEINOSUKE, SYNTHESIS (BRD),(1990) N, C. 768-770
  作者：YAMADA, YOICHI、YASUDA, HEINOSUKE

  DOI：——

  日期：——