(E)-2-methoxycarbonyl-5-phenyl-2-prop-2-ynylpent-4-enoic acid | 137742-20-2

• 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: (E)-2-methoxycarbonyl-5-phenyl-2-prop-2-ynylpent-4-enoic acid
• CAS: 137742-20-2
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: DOIDCONFZWWCMQ-JXMROGBWSA-N

物化性质

• 沸点：
  452.7±45.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-methoxycarbonyl-5-phenyl-2-prop-2-ynylpent-4-enoic acid 在 gold (III) oxide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以79%的产率得到3-methoxycarbonyl-5-methylene-3-(3-phenylprop-2-enyl)-γ-butyrolactone
  参考文献：
  名称：

  Au₂O₃ as a Stable and Efficient Catalyst for the Selective Cycloisomerization of γ-Acetylenic Carboxylic Acids to γ-Alkylidene-γ-Butyrolactones

  摘要：

  展示了市售金氧化物（Au2O3）作为催化剂，在通过一种通用、高效且简便的过程，将带有羧酸的炔烃环化为相应γ-烷叉基-γ-丁内酯中的高潜力。该反应表现出高度化学选择性、区域选择性和立体选择性。5-内型环化和反式金化是Au2O3催化剂的普遍趋势。

  DOI：

  10.1055/s-2008-1032108

文献信息

• Palladium-catalyzed reaction of vinyl triflates and vinyl/aryl halides with 4-alkynoic acids: regio- and stereoselective synthesis of (E)-.delta.-vinyl/aryl-.gamma.-methylene-.gamma.-butyrolactones
  作者：Antonio Arcadi、Alfredo Burini、Sandro Cacchi、Monica Delmastro、Fabio Marinelli、Bianca Rosa Pietroni

  DOI：10.1021/jo00029a035

  日期：1992.1

  The palladium-catalyzed reaction of vinyl triflates and vinyl/aryl halides with 4-pentynoic acid, 2,2-disubstituted 4-pentynoic acids, and 5-substituted 4-pentynoic acids produced regio- and stereoselectively the corresponding (E)-delta-vinyl/aryl-gamma-methylene-gamma-butyrolactones in good to high yield. Reactions were carried out in the presence of catalytic amounts of Pd(OAc)2(PPh3)2 or Pd(PPh3)4, Et3N, and n-Bu4NCl. The presence of chloride anions was found to be necessary to obtain the best results. The proposed mechanism involves an intramolecular nucleophilic attack of the carboxylate anion on the palladium-coordinated carbon-carbon triple bond and subsequent reductive elimination of Pd(0) species from the resulting sigma-vinylpalladium complex which regenerates the catalyst and releases the exocyclic enol lactone.
• Room Temperature Au(I)-Catalyzed <i>exo</i>-Selective Cycloisomerization of Acetylenic Acids:  An Entry to Functionalized γ-Lactones
  作者：Emilie Genin、Patrick Yves Toullec、Sylvain Antoniotti、Célia Brancour、Jean-Pierre Genêt、Véronique Michelet

  DOI：10.1021/ja056857j

  日期：2006.3.1

  A highly efficient gold-catalyzed cyclization reaction of various functionalized acetylenic acids is described. The cyclizations are conducted in the presence of Au(I) catalyst in acetonitrile at room temperature in a short reaction time. The reaction conditions are compatible with several functional groups, such as ester, alkene, alkyne, chloro, and free or protected alcohol, and lead to original gamma-lactones in good to excellent yields.