3-vinyl-2(5H)-furanone | 238433-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-vinyl-2(5H)-furanone
• 英文别名: 3-Vinylfuran-2(5h)-one；4-ethenyl-2H-furan-5-one
• CAS: 238433-82-4
• 化学式: C₆H₆O₂
• 分子量: 110.112
• InChiKey: ZHCVVUYVRCVOAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-vinyl-2(5H)-furanone 在 2,6-二叔丁基-4-甲基苯酚 作用下， 以 氘代氯仿 为溶剂， 反应 24.0h， 生成 、 (+/-)-differolide
  参考文献：
  名称：

  An Enyne Metathesis/(4 + 2)- Dimerization Route to (±)-Differolide

  摘要：

  [GRAPHICS]A concise total synthesis of (+/-)-differolide (1) has been achieved. 2-Vinylbutenolide (2) was prepared by enyne metathesis of allyl propynoate (3) using the Grubbs initiator 4, This reaction was examined by H-1 NMR spectroscopy, which led to the hypothesis that low concentration of ruthenium species and high concentration of enyne substrate would be advantageous. Accordingly, slow addition of 4 to solutions of enyne 3 was found to be beneficial. Spontaneous dimerization of 2 gave (+/-) differolide (1) and an isomer.

  DOI：

  10.1021/ol9905912
• 作为产物：
  描述：

  戊-4-烯-2-炔-1-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 lithium aluminium tetrahydride 、 碘 、 sodium methylate 、 potassium carbonate 、 一水合肼 作用下， 以 四氢呋喃 为溶剂， 20.0~35.0 ℃ 、506.62 kPa 条件下， 反应 24.0h， 生成 3-vinyl-2(5H)-furanone
  参考文献：
  名称：

  Development of a Method for the Synthesis of a-Substituted a,b-Unsaturated Lactones Based on Stille-Type Pd-catalyzed Carbonylation of (Z)-w-Iodoalkenols. An Efficient and Selective Synthesis of (+)-Hamabiwa-lactone B

  摘要：

  DOI：

  10.3987/com-99-s138

文献信息

• ANDROGRAPHOLIDE DERIVATIVES AND USE THEREOF IN MANUFACTURE OF MEDICAMENTS
  申请人：Panorama Research Inc.

  公开号：EP2176255B1

  公开（公告）日：2012-02-29
• Hydroxamate compositions
  申请人：Covidien LP

  公开号：EP2177226B1

  公开（公告）日：2013-09-18
• Development of a Method for the Synthesis of a-Substituted a,b-Unsaturated Lactones Based on Stille-Type Pd-catalyzed Carbonylation of (Z)-w-Iodoalkenols. An Efficient and Selective Synthesis of (+)-Hamabiwa-lactone B
  作者：Ei-ichi Negishi、Baiqiao Liao

  DOI：10.3987/com-99-s138

  日期：——
• An Enyne Metathesis/(4 + 2)- Dimerization Route to (±)-Differolide
  作者：Thomas R. Hoye、Scott M. Donaldson、Tricia J. Vos

  DOI：10.1021/ol9905912

  日期：1999.7.1

  [GRAPHICS]A concise total synthesis of (+/-)-differolide (1) has been achieved. 2-Vinylbutenolide (2) was prepared by enyne metathesis of allyl propynoate (3) using the Grubbs initiator 4, This reaction was examined by H-1 NMR spectroscopy, which led to the hypothesis that low concentration of ruthenium species and high concentration of enyne substrate would be advantageous. Accordingly, slow addition of 4 to solutions of enyne 3 was found to be beneficial. Spontaneous dimerization of 2 gave (+/-) differolide (1) and an isomer.