diethyl (Z)-2-(2,5-dioxo-1-pyrrolidinyl)-2-butenedioate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl (Z)-2-(2,5-dioxo-1-pyrrolidinyl)-2-butenedioate
• 英文别名: diethyl 2-(2,5-dioxo-1-pyrrolidinyl)-2-butenedioate；diethyl (Z)-2-(2,5-dioxopyrrolidin-1-yl)but-2-enedioate
• 化学式: C₁₂H₁₅NO₆
• 分子量: 269.254
• InChiKey: IYJWPMKVCQCQLJ-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  diethyl 2-(succinimido)-3-(triphenylphosphoranylidene)-butanedioate 在 sodium dihydrogenphosphate 作用下， 反应 0.08h， 生成 diethyl (Z)-2-(2,5-dioxo-1-pyrrolidinyl)-2-butenedioate
  参考文献：
  名称：

  在无溶剂条件下，在磷酸二氢钾和磷酸二氢钠存在的情况下，微波诱导的二烷基 2-(亚氨基-N-基)-3-(三苯基亚膦基)丁二酸酯向缺电子 (Z)-N-乙烯基亚胺的立体选择性转化

  摘要：

  摘要 磷酸二氢钾粉末和磷酸二氢钠粉末可在无溶剂条件下催化 2-(亚氨基-N-基)-3-(三苯基亚膦基)丁二酸二烷基酯立体选择性转化为缺电子 (Z)-N-乙烯基酰亚胺。在微波照射下 5-6 分钟，转化率高。

  DOI：

  10.1080/10426500590917399

文献信息

• Reaction between Imides and Electron‐Poor Acetylenic Esters in the Presence of Dipotassium Hydrogen Phosphate Powder in Solvent‐Free Conditions: An Efficient Method for the Synthesis of Electron‐Poor <i>N</i>‐Vinyl Imides
  作者：Ali Ramazani、Mahsa Kardan、Nader Noshiranzadeh

  DOI：10.1080/00397910701771058

  日期：2008.1.1

  A two-component condensation reaction between an imide and an electron-poor acetylenic ester efficiently provides substituted electron-poor N-vinyl imides in a one-pot reaction in the presence of dipotassium hydrogen phosphate powder in solvent-free conditions. The reaction is fairly stereoselective.
• Tributylphosphine Catalyzed Stereoselective N -Vinylation of Phthalimide and Succinimide
  作者：Ali Ramazani、Nader Noshiranzadeh、Bagher Mohammadi

  DOI：10.1080/10426500307921

  日期：2003.3.1

  Protonation of the highly reactive 1:1 intermediates produced in the reaction between tributylphosphine and dialkyl acetylenedicarboxylates by imides (phthalimide and succinimide) leads to vinyltributylphosphonium salts, which undergo an addition-elimination reaction in CH2Cl2 at room temperature to produce the corresponding N-vinylimides (Z isomers) in excellent yields.
• Silica-Gel Catalyzed Stereoselective Conversion of Dialkyl 2-(Imido-<i>N</i>-YL)-3- (triphenylstibanylidene)succinates to Electron-Poor (<i>Z</i>)-<i>N</i>-Vinylimides in Solvent-Free Conditions
  作者：Ali Ramazani、Ebrahim Ahmadi

  DOI：10.1080/104265090902787

  日期：2005.9.1

  Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylstibine and dialkyl acetylenedicarboxylates, by imides (phthalimide and succinimide) leads to vinyltriphenylstibinium salts, which undergo a Michael addition reaction with a conjugate base to produce dialkyl 2-(imido-N-yl)3-(triphenylstibanylidene)succinates. Silica gel was found to catalyze the stereoselective conversion of dialkyl 2-(imido-N-yl)-3-(triphenylstibanylidene)succinates to electron-poor (Z)-N-vinylimides in solvent-free conditions at 97 degrees C in high conversions.
• MAGNESIUM HYDROGEN SULFATE POWDER CATALYZED STEREOSELECTIVE CONVERSION OF DIALKYL 2-(IMIDO-<i>N</i> -YL)-3-(TRIPHENYLPHOSPHORANYLIDENE)- BUTANEDIOATES TO ELECTRON-POOR (<i>Z</i>)-<i>N</i> -VINYLIMIDES IN SOLVENT-FREE CONDITIONS
  作者：Ali Ramazani、Ebrahim Ahmadi

  DOI：10.1080/10426500490422218

  日期：2004.3.1

  Magnesium hydrogen sulfate powder was found to catalyze stereoselective conversion of dialkyl 2-(imido-N-yl)-3-(triphenylphosphoranylidene)butanedioates to electron-poor (Z)-N-vinylimides in solvent-free conditions at 95degreesC 1 h in high conversions. Microwave also was found to catalyze the same reactions in the presence of magnesium hydrogen sulfated powder in solvent-free conditions in 3 min.
• Microwave-Induced Stereoselective Conversion of Stabilized Phosphorus Ylides to Electron Poor (<i>Z</i>)-<i>N</i>-Vinylimides in the Presence of Supported Catalysts on Silica Gel in Solvent-Free Conditions
  作者：Ali Reza Kazemizadeh、Ebrahim Ahmadi、Farzin Marandi、Ali Ramazani

  DOI：10.1080/10426500701521837

  日期：2007.10.18

  Supported catalyst on silica-gel were found to catalyze stereoselective conversion of dialkyl 2-(imido-N-yl)-3-triphetiylphosphoranylidene butanedioates to electron-poor (Z)-N-vinylimides in solvent-free conditions under microwave irradiation. in 2 to 3 minutes in high conversions. The reaction is completely stereoselective.