3,3-二甲基-5-乙烯基二氢呋喃-2(3H)-酮 | 154033-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 3,3-二甲基-5-乙烯基二氢呋喃-2(3H)-酮
• 英文名称: 3,3-dimethyl-5-vinyldihydrofuran-2(3H)-one
• 英文别名: 5-ethenyl-3,3-dimethyloxolan-2-one
• CAS: 154033-18-8
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: KMTFRUUFACGXTP-UHFFFAOYSA-N

物化性质

• 熔点：
  30 °C
• 沸点：
  214.5±29.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-dimethyl-4,5-dehydro ε-lactone 在 aluminum tris(2,6-diphenylphenoxide) 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 生成 3,3-二甲基-5-乙烯基二氢呋喃-2(3H)-酮
  参考文献：
  名称：

  Substrate Encapsulation: An Efficient Strategy for the RCM Synthesis of Unsaturated ϵ-Lactones

  摘要：

  A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.

  DOI：

  10.1021/ol8022227

文献信息

• Escape from Hydrofunctionalization: Palladium Hydride‐Enabled Difunctionalization of Conjugated Dienes and Enynes
  作者：Ziyan Zhang、Vladimir Gevorgyan

  DOI：10.1002/anie.202311848

  日期：2023.11.20

  A palladium hydride-catalyzed difunctionalization of dienes and enynes is reported. This mild protocol harnesses visible light to enhance the hydricity of PdH species, enabling a chemoselectivity switch of the hydropalladation step. This method allows for annulation of dienes and enynes with abundant substrates, such as acrylic acids, acrylic amides, and Baylis–Hillman adducts, toward alkenyl or alkynyl

  据报道，氢化钯催化的二烯烃和烯烃的二官能团化。这种温和的方案利用可见光来增强 PdH 物质的水流动性，从而实现 hydropalladation 步骤的化学选择性切换。该方法允许将具有丰富底物（如丙烯酸、丙烯酸酰胺和 Baylis-Hillman 加合物）的二烯烃和烯烃环化为烯基或炔基内酯、内酰胺和四氢呋喃。
• Expeditious formation of γ-lactones upon palladium-catalyzed double nucleophilic addition of bis(TMS)ketene acetals to vicinal allylacetates
  作者：Cesar Sandoval Chavez、Henri Rudler、Andrée Parlier、Patrick Herson

  DOI：10.1016/j.tetlet.2008.07.111

  日期：2008.10

  Polysubstituted gamma-lactones are easily obtained, in one step, upon the interaction of bis(TMS)ketene acetals with vicinal allylic acetates in the presence of catalytic amounts of Pd(PPh3)(4). (C) 2008 Elsevier Ltd. All rights reserved.
• Substrate Encapsulation: An Efficient Strategy for the RCM Synthesis of Unsaturated ϵ-Lactones
  作者：Emily B. Pentzer、Tendai Gadzikwa、SonBinh T. Nguyen

  DOI：10.1021/ol8022227

  日期：2008.12.18

  A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.