diethyl 2,3-dicyanosuccinate | 51939-81-2

• 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: diethyl 2,3-dicyanosuccinate
• 英文别名: dl-diethyl dicyanosuccinate；diethyl 2,3-dicyanobutanedioate；2,3-dicyano-succinic acid diethyl ester；2,3-Dicyan-bernsteinsaeure-diaethylester
• CAS: 51939-81-2
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: IQGKBEMBMYSFIV-UHFFFAOYSA-N

物化性质

• 沸点：
  190-200 °C(Press: 10 Torr)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  diethyl 2,3-dicyanosuccinate 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-(Biphenyl-4-ylsulfanyl)-4-cyano-5-ethoxy-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  MEK inhibitors: The chemistry and biological activity of U0126, its analogs, and cyclization products

  摘要：

  In search of antiinflammatory drugs with a new mechanism of action, U0126 was found to functionally antagonize AP-1 transcriptional activity via noncompetitive inhibition of the dual specificity kinase MEK with, an IC50 of 0.07 mu M for MEK 1 and 0.06 mu M for MEK 2. U0126 can undergo isomerization and cyclization reactions to form a variety of products, both chemically and in vivo, all of which exhibit less affinity for MEK and lower inhibition of AP-1 activity than parent, U0126. (C) 1998 The DuPont Merck Pharmaceutical Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00522-8
• 作为产物：
  描述：

  (2E)-2,3-二氰基-2-丁烯二酸 1,4-二乙基酯 在 乙醇 、 铂 作用下， 生成 diethyl 2,3-dicyanosuccinate
  参考文献：
  名称：

  某些酯，腈和酯腈的红外光谱

  摘要：

  DOI：

  10.1039/jr9550002170

文献信息

• Dialkyl Dicyanofumarates as Oxidizing Reagents for the Conversion of Thiols into Disulfides and Selenols into Diselenides
  作者：Grzegorz Mlostoń、Antonella Capperucci、Damiano Tanini、Róża Hamera-Fałdyga、Heinz Heimgartner

  DOI：10.1002/ejoc.201701066

  日期：2017.12.15

  thiols react smoothly with dialkyl dicyanofumarates in CH2Cl2 at room temperature to give the corresponding disulfides in excellent yields. Aliphatic 1,2-, 1,3-, and 1,4-dithiols afford cyclic disulfides. Analogous reaction courses were observed starting with selenols, and the required diselenides were also formed in nearly quantitative yields. In all of the reactions, dialkyl dicyanosuccinates formed

  在室温下，脂肪族和芳香族硫醇与二氰基富马酸二烷基酯在 CH2Cl2 中顺利反应，以优异的产率得到相应的二硫化物。脂肪族 1,2-、1,3- 和 1,4- 二硫醇提供环状二硫化物。从硒醇开始观察到类似的反应过程，并且所需的二硒化物也以几乎定量的产率形成。在所有反应中，二氰基琥珀酸二烷基酯以非对映异构体的 1:1 混合物形式形成，作为唯一的其他产物。半胱胺（2-巯基乙胺）表现不同；伯胺基团的迈克尔加成导致二氰基富马酸酯完全消耗，并且形成含有烯胺部分的二硫化物而没有形成二氰基琥珀酸酯。
• An unexpected reaction of diethyl phosphite with electron-deficient dialkyl dicyanofumarates
  作者：Grzegorz Mlostoń、Małgorzata Celeda、Heinz Heimgartner

  DOI：10.1080/10426507.2015.1085045

  日期：2016.2.1

  ABSTRACT Abstract Diethyl phosphite reacts with both dimethyl dicyanofumarate and dicyanomaleate in boiling 1,2-dichloroethane to yield, after chromatographic workup, a 1:1-mixture of the corresponding meso- and dl-dicyanosuccinates. The analogous transformation was observed in the cases of diethyl and diisopropyl dicyanofumarates. A reaction pathway via initial formation of a P–C bond followed by its

  图形摘要 摘要 亚磷酸二乙酯与二氰基富马酸二甲酯和二氰基苹果酸在沸腾的 1,2-二氯乙烷中反应，经色谱处理后，得到相应的内消旋和 dl-二氰基琥珀酸酯的 1:1 混合物。在二氰基富马酸二乙酯和二异丙基酯的情况下观察到类似的转化。提出了通过初始形成 P-C 键然后水解裂解的反应途径。
• The Synthesis of Heterocycles from Indolin-2-one Derivatives and Active Methylene Reagents
  作者：Fathy F. Abdel-Latif、Ramadan A. Mekheimer、Mohamed M. Mashaly、Essam Kh. Ahmed

  DOI：10.1135/cccc19941235

  日期：——

  Investigation the synthesis of multifunctionalized heterocyclic spiro derivatives via the reaction of isatin, ethyl cyanoacetate and an other active methylene compound. It has been found that refluxing of an ethanolic piperidine solution of equimolar ratios of isatin (Ia), ethyl cyanoacetate (II) and barbituric acid (IIIa) or thiobarbituric acid (IIIb) afforded a solid product whose structure was assumed, in accordance with elemental analysis and IR and ¹H NMR spectra, to be VIIIa and VIIIb. Confirmation of the structures VIIIa and VIIIb follows from their preparation from compound IV, synthesized separately, and barbituric acids IIIa and IIIb in 1 : 1 molar ratio under the same reaction conditions.

  通过对异吲哚、乙基氰乙酸酯和另一种活性亚甲基化合物的反应合成多官能杂环螺环衍生物的研究。发现，在等摩尔比的异吲哚（Ia）、乙基氰乙酸酯（II）和巴比妥酸（IIIa）或硫巴比妥酸（IIIb）的乙醇哌嗪溶液中回流，得到了一种固体产物，根据元素分析、红外光谱和1H核磁共振谱，认为其结构为VIIIa和VIIIb。VIIIa和VIIIb的结构确认来自于它们在相同反应条件下，通过分别合成的化合物IV和巴比妥酸IIIa、IIIb按照1：1摩尔比制备而成。
• Potassium Fluoride on Alumina: Oxidative Coupling of Acidic Carbon Compounds with Diiodine
  作者：Didier Villemin、Abdelkrim Ben Alloum

  DOI：10.1080/00397919208021130

  日期：1992.12

  Diiodine reacts at room temperature with activated methylene compounds in the presence of potassium fluoride on alumina and saturated dimers, unsaturated dimers or trimers were formed according to the stoechiometry of the reaction. The reactions were improved by using ultrasound activation.
• Knowles, Philip; Harris, Neil V., Journal of the Chemical Society. Perkin transactions I, 1983, # 7, p. 1475 - 1477
  作者：Knowles, Philip、Harris, Neil V.

  DOI：——

  日期：——