diethyl benzoylbutendicarboxylate | 79742-18-0

• 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: diethyl benzoylbutendicarboxylate
• 英文别名: diethyl 2-benzoylfumarate；diethyl 2-benzoylbut-2-enedioate；2-benzoylbut-2-enedioic acid diethyl ester；Diethyl 2-benzoylbut-2-enedioate
• CAS: 79742-18-0
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: IUHBXWZTJTWXLV-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  154-156 °C(Press: 0.8 Torr)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl benzoylbutendicarboxylate 、 4-氯苯甲酰氯 在 三丁基膦 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以83%的产率得到diethyl 2-(4-chlorophenyl)-5-phenylfuran-3,4-dicarboxylate
  参考文献：
  名称：

  磷内酯为中间体的分子内维蒂希反应制备四取代呋喃

  摘要：

  实现了从迈克尔受体，三丁基膦和酰氯开始的四取代呋喃的新制备方法。在室温下，只需一步即可在10分钟至21小时内以中等到高收率（60-99％）的方式高效生成各种功能强大的呋喃。该反应被建议通过分子内的维蒂希型反应进行，使用磷化磷作为中间体。

  DOI：

  10.1021/ol101080q
• 作为产物：
  描述：

  苯甲醛 、 丁炔二酸二乙酯 在 三乙胺 、 1,3-二异丙基咪唑氯 、 gold(I) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以70%的产率得到diethyl benzoylbutendicarboxylate
  参考文献：
  名称：

  Two tandem sequential reactions catalyzed by [Au], N-heterocyclic carbenes (NHC) and organic bases

  摘要：

  Herein we describe two coupling reactions of aldehydes and activated alkynes to give chalcones or alkenyl esters depending on the base used. Chalcones were obtained by activation of alkynes by Au-I and of aldehydes by NHC in presence of triethylamine. Alkenyl esters were obtained via generation of gold nanoparticles, aerial oxidation of aldehydes to carboxylates and their subsequent nucleophilic addition to the alkyne functionality. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.135

文献信息

• Ring-Opening of 4-Isoxazolines: Competitive Formation of Enamino Derivatives and a,b-Enones
  作者：Ugo Chiacchio、Franco Casuscelli、Angelo Liguori、Antonio Rescifina、Giovanni Romeo、Giovanni Sindona、Nicola Uccella

  DOI：10.3987/com-92-6223

  日期：——

  Ring-opening of 3-substituted 4-isoxazolines, proceeding through the intermediate isoxazolinium salts, follows two competing reaction pathways leading to alpha,beta-enones and enamines respectively. The rearrangement courses can be controlled as a function of substitution pattern and experimental conditions.
• Cerium-Catalyzed Formal Cycloaddition of Cycloalkanols with Alkenes through Dual Photoexcitation
  作者：Anhua Hu、Yilin Chen、Jing-Jing Guo、Na Yu、Qing An、Zhiwei Zuo

  DOI：10.1021/jacs.8b08781

  日期：2018.10.24

  We describe a synergistic utilization of cerium photocatalysis and photoinduced electron transfer catalysis that enables an atom- and step-economical ring expansion of readily available cycloalkanols. This operationally simple protocol provides rapid access to privileged and synthetically challenging bridged lactones. The mild catalytic manifold has been adapted to continuous flow for scale-up applications and employed for the concise synthesis of polycyclic core of nepalactones.
• Additionen von Aldehyden an aktivierte Doppelbindungen; XXXI¹. Synthesen und Reaktionen von verzweigten Tetracarbonyl-Verbindungen
  作者：Hermann Stetter、Friedrich Jonas

  DOI：10.1055/s-1981-29549

  日期：——
• Preparation of Tetrasubstituted Furans via Intramolecular Wittig Reactions with Phosphorus Ylides as Intermediates
  作者：Tzu-Ting Kao、Siang-en Syu、Yi-Wun Jhang、Wenwei Lin

  DOI：10.1021/ol101080q

  日期：2010.7.2

  functional furans can be efficiently generated in one step at room temperature within 10 min to 21 h in moderate to high yields (60−99%). The reaction was proposed to proceed via intramolecular Wittig-type reactions, using phosphorus ylides as intermediates.

  实现了从迈克尔受体，三丁基膦和酰氯开始的四取代呋喃的新制备方法。在室温下，只需一步即可在10分钟至21小时内以中等到高收率（60-99％）的方式高效生成各种功能强大的呋喃。该反应被建议通过分子内的维蒂希型反应进行，使用磷化磷作为中间体。
• Two tandem sequential reactions catalyzed by [Au], N-heterocyclic carbenes (NHC) and organic bases
  作者：Mauro F.A. Adamo、Gea Bellini、Surisetti Suresh

  DOI：10.1016/j.tet.2011.05.135

  日期：2011.8

  Herein we describe two coupling reactions of aldehydes and activated alkynes to give chalcones or alkenyl esters depending on the base used. Chalcones were obtained by activation of alkynes by Au-I and of aldehydes by NHC in presence of triethylamine. Alkenyl esters were obtained via generation of gold nanoparticles, aerial oxidation of aldehydes to carboxylates and their subsequent nucleophilic addition to the alkyne functionality. (C) 2011 Elsevier Ltd. All rights reserved.