dl-dimethyl dicyanosuccinate

• 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: dl-dimethyl dicyanosuccinate
• 英文别名: dimethyl 2,3-dicyanobutanedioate
• 化学式: C₈H₈N₂O₄
• 分子量: 196.163
• InChiKey: YQSOWPIPZFBSMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  5
• 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

• 作为产物：
  描述：

  Methyl 3,4-dicyano-2,2,5-trimethoxyfuran-3-carboxylate 在 水 作用下， 以80%的产率得到dl-dimethyl dicyanosuccinate
  参考文献：
  名称：

  Reactions of Dimethoxycarbene with Dimethyl 2,3-Dicycanomaleate and Fumarate

  摘要：

  Dimethoxycarbene, in 2-fold or larger excess, reacts with dimethyl 2,3-dicyanomaleate and fumarate to afford an unstable dihydrofuran 1:1 adduct that was shown to react further with the carbene to afford a 2:1 adduct reported previously. In an astonishing process, the dihydrofuran reacts with water to afford a mixture of (d,l and meso) dimethyl 2,3-dicyanosuccinates in which both hydrogen atoms of water were used to hydrogenate a CC bond.

  DOI：

  10.1021/ol071143u

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。
• Reactions of Dimethoxycarbene with Dimethyl 2,3-Dicycanomaleate and Fumarate
  作者：Anna Sliwinska、John Warkentin

  DOI：10.1021/ol071143u

  日期：2007.6.1

  Dimethoxycarbene, in 2-fold or larger excess, reacts with dimethyl 2,3-dicyanomaleate and fumarate to afford an unstable dihydrofuran 1:1 adduct that was shown to react further with the carbene to afford a 2:1 adduct reported previously. In an astonishing process, the dihydrofuran reacts with water to afford a mixture of (d,l and meso) dimethyl 2,3-dicyanosuccinates in which both hydrogen atoms of water were used to hydrogenate a CC bond.