Dimethyl 2-cyanoethylene-1,1-dicarboxylate | 62693-70-3

• 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: Dimethyl 2-cyanoethylene-1,1-dicarboxylate
• 英文别名: dimethyl 2-cyanoethene-1,1-dicarboxylate；2-cyano-1,1-bis(methoxycarbonyl)ethene；dimethyl cyanomethylidenemalonate；2-cyano-ethene-1,1-dicarboxylic acid dimethyl ester；Propanedioic acid, (cyanomethylene)-, dimethyl ester；dimethyl 2-(cyanomethylidene)propanedioate
• CAS: 62693-70-3
• 化学式: C₇H₇NO₄
• 分子量: 169.137
• InChiKey: RZGODCPGVINVQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Dimethyl 2-cyanoethylene-1,1-dicarboxylate 、 茴香烯 以 氘代氯仿 为溶剂， 以50%的产率得到
  参考文献：
  名称：

  Transition from concerted to stepwise [2 + 4] cycloaddition reactions of .alpha.,.beta.-unsaturated carboxylic esters

  摘要：

  DOI：

  10.1021/jo00169a037
• 作为产物：
  描述：

  二甲基氧代丙二酸酯 、 (三苯基膦)乙腈 以 苯 为溶剂， 生成 Dimethyl 2-cyanoethylene-1,1-dicarboxylate
  参考文献：
  名称：

  A Simple Route to Alkenes having Three Electron-Withdrawing Substituents at the Double Bond

  摘要：

  DOI：

  10.1055/s-1977-24504

文献信息

• Addition d'azides a des olefines trisubstituees par des groupements electroattracteurs
  作者：Mohand Saïd Ouali、Michel Vaultier、Robert Carrié

  DOI：10.1016/0040-4020(80)80081-0

  日期：1980.1

  The reaction of benzyl, methyl and phenyl azide, with olefins substituted by three electron-withdrawing groups, has been studied. This reaction gives in certain cases only one triazoline (single orientation of the cycloaddition). In other cases, a mixture of a triazoline and a diazocompound (double orientation of the cycloaddition) is obtained. The structure assignment of the triazolines is confirmed

  研究了苄基，甲基和苯基叠氮化物与被三个吸电子基团取代的烯烃的反应。在某些情况下，该反应仅产生一个三唑啉（环加成的单取向）。在其他情况下，获得三唑啉和重氮化合物的混合物（环加成的双重取向）。使用化学方法和13 C-NMR证实了三唑啉的结构分配。在热方面，重氮化合物重排成烯酸酯，后者在高温下环化成喹啉。
• a(<i>E</i>)-1-Methoxy-1,3-butadiene and 1,1-Dimethoxy-1,3-butadiene in (4 + 2) Cycloadditions. A Mechanistic Comparison
  作者：Reiner Sustmann、Surajin Tappanchai、Heinz Bandmann

  DOI：10.1021/ja961390l

  日期：1996.1.1

  The reactions of (E)-1-methoxy-1,3-butadiene (1) and 1,1-dimethoxy-1,3-butadiene (2) with a series of dienophiles of increasing electrophilicity are described Stereochemical studies reveal that the cycloadditions of 1 are concerted processes, even for the most electron-deficient olefins dimethyl dicyanofumarate and dimethyl dicyanomaleate. 1,1-Dimethoxy-1,3-butadiene reacts under our conditions (dilute solutions and temperatures less than or equal to 60 degrees C) only with those dienophiles which can give zwitterions out of the antiperiplanar conformation of the diene. Zwitterionic intermediates can be trapped by methanol. In the case of tetracyanoethene the kinetics of decay of an intermediate, interpreted as the zwitterion, can be followed by stopped flow techniques: E(a) = 14.8 +/- 0.2 kcal mol(-1), log A = 11.9 +/- 0.1, Delta H double dagger = 10.8 +/- 0.1 kcal mol(-1), Delta S double dagger = -6.2 +/- 0.1 cal mol(-1) K-1, and Delta G double dagger = 11.40 +/- 0.03 kcal mol(-1).
• Sustmann, Reiner; Siangouri-Feulner, Ioana, Chemische Berichte, 1993, vol. 126, # 5, p. 1241 - 1246
  作者：Sustmann, Reiner、Siangouri-Feulner, Ioana

  DOI：——

  日期：——
• Rese, Michael; Dern, Mechthild; Luecking, Karin, Liebigs Annalen, 1995, # 7, p. 1139 - 1152
  作者：Rese, Michael、Dern, Mechthild、Luecking, Karin、Sustmann, Reiner

  DOI：——

  日期：——
• Luecking, Karin; Rese, Michael; Sustmann, Reiner, Liebigs Annalen, 1995, # 7, p. 1129 - 1138
  作者：Luecking, Karin、Rese, Michael、Sustmann, Reiner

  DOI：——

  日期：——