dimethyl 2-(succinimido-N-yl)-3-(triphenylphosphoranylidene)butanedioate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 2-(succinimido-N-yl)-3-(triphenylphosphoranylidene)butanedioate
• 英文别名: dimethyl 2-(succinimide-N-yl)-3-(triphenylphosphanylidene)butanedioate；dimethyl 2-(succinimido)-3-(triphenylphosphoranylidene)-butanedioate；Dimethyl 2-(2,5-dioxopyrrolidin-1-yl)-3-(triphenyl-lambda5-phosphanylidene)butanedioate；dimethyl 2-(2,5-dioxopyrrolidin-1-yl)-3-(triphenyl-λ5-phosphanylidene)butanedioate
• 化学式: C₂₈H₂₆NO₆P
• 分子量: 503.491
• InChiKey: DAWVYWCOXMRLMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(succinimido-N-yl)-3-(triphenylphosphoranylidene)butanedioate 在 sodium dihydrogenphosphate 作用下， 反应 0.08h， 生成 dimethyl (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
• 作为产物：
  描述：

  丁二酰亚胺 、 丁炔二酸二甲酯 、 三苯基膦 以 乙酸乙酯 为溶剂， 反应 24.0h， 以95%的产率得到dimethyl 2-(succinimido-N-yl)-3-(triphenylphosphoranylidene)butanedioate
  参考文献：
  名称：

  从酰亚胺或乙酰苯胺衍生物衍生的稳定磷烷的简单合成

  摘要：

  通过三苯基膦、乙炔二羧酸二烷基酯和强 NH 酸（例如乙酰苯胺、4-甲基乙酰苯胺、2-氰基乙酰苯胺、4-溴乙酰苯胺、4-甲氧基乙酰苯胺）之间的 1:1:1 加成反应，以极好的收率获得稳定的结晶磷叶立德，琥珀酰亚胺、马来酰亚胺或邻苯二甲酰亚胺。这些稳定的正膦以两种几何异构体的混合物形式存在，这是由于叶立德部分与相邻羰基的共轭导致围绕碳-碳部分双键的旋转受限。

  DOI：

  10.1080/10426500214569

文献信息

• ONE-STEP, THREE-COMPONENT SYNTHESIS OF DIALKYL 2-(IMIDO-<i>N</i>-YL)-3-(TRIPHENYLPHOSPHORANYLIDENE) BUTANEDIOATES
  作者：Ali Ramazani、Homaira Ahani

  DOI：10.1080/10426500108040594

  日期：2001.3.1

  Abstract A one-step synthesis of dialkyl 2-(imido-N-yl)-3-(triphenylphosphoranylidene)butandioates in fairly good yields by the reaction of imides, dialkyl acetylenedicarboxylates and triphenlphosphine is reported. The structures of these compounds were confirmed by IR, MS and 1H, 31P and 13C NMR spectroscopy, and elemental analyses. The NMR spectra indicated that the compounds (CDCl3 as solvent) contained

  摘要 报道了通过酰亚胺、乙炔二羧酸二烷基酯和三苯基膦反应以相当好的收率一步合成 2-(亚氨基-N-基)-3-(三苯基亚膦基)丁二酸二烷基酯的方法。这些化合物的结构通过 IR、MS 和 1H、31P 和 13C NMR 光谱以及元素分析得到证实。NMR 谱表明化合物（CDCl3 作为溶剂）包含两个旋转异构体，每个叶立德的数量不等。
• Microwave-Induced Stereoselective Conversion of Dialkyl 2-(Imido-<i>N</i>-yl)-3-(triphenylphosphoranylidene) butanedioates to Electron-Poor (<b> <i>Z</i> </b>)-<b> <i>N</i> </b>-Vinylimides in the Presence of Potassium Dihydrogen Phosphate and Sodium Dihydrogen Phosphate in Solvent-Free Conditions
  作者：Ali Ramazani、Ali Reza Kazemizadeh、Farzin Marandi

  DOI：10.1080/10426500590917399

  日期：2005.7.1

  Abstract Potassium dihydrogen phosphate powder and sodium dihydrogen phosphate powder were found to catalyze stereoselective conversion of dialkyl 2-(imido-N-yl)- 3-(triphenylphosphoranylidene)butanedioates to electron-poor (Z)-N-vinylimides in solvent-free conditions under microwave irradiation in 5-6 minutes in high conversions.

  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。
• A Facile One-Pot Synthesis of Highly-Functionalized Stable Heterocyclic Phosphorus Ylides in Aqueous Media
  作者：Mohammad Reza Islami、Zahra Hassani、Hassan Sheibani

  DOI：10.1080/10426500214559

  日期：2002.11.1

  Phthalimide or succinimide undergo a reaction with dialkyl acetylene-dicarboxylates and triphenylphosphine to produce highly-functionalized stable heterocyclic phosphorus ylides in good yields in water-tetrahydrofuran (6:1). This methodology is of interest because of the use of water as solvent, thus minimizing the cost, operational hazards, and environmental pollution.
• 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.
• Silica Gel Catalyzed Stereoselective Conversion of Dialkyl 2-(Imido- N -YL)-3-(triphenylphosphoranylidene)-butanedioates to Electron-Poor ( Z )- N -Vinylimides in Solvent-Free Conditions
  作者：Ali Ramazani、Ebrahim Ahmadi

  DOI：10.1080/713744565

  日期：2003.10.1

  Silica gel was found to catalyze the stereoselective conversion of dialkyl 2-(imido-N-yl)-3-(triphenylphosphoranylidene)butanedioates to electron-poor (Z)-N-vinylimides in solvent-free conditions at 95degreesC in high coversions.