5-styryl-dihydro-furan-2-one | 114361-75-0

• 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: 5-styryl-dihydro-furan-2-one
• 英文别名: 5-styryldihydrofuran-2(3H)-one；5-styryl-tetrahydrofuran-2-one；5-(2-Phenylethenyl)oxolan-2-one；5-(2-phenylethenyl)oxolan-2-one
• CAS: 114361-75-0
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: NIJXYOQCZNHOAX-UHFFFAOYSA-N

物化性质

• 沸点：
  357.9±31.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  1-phenylhex-1,5-dien-3-ol 在 叔丁基过氧化氢 、 新铜试剂 、 水 、 copper dichloride 、 palladium dichloride 作用下， 以 硝基甲烷 为溶剂， 反应 24.0h， 以31%的产率得到5-styryl-dihydro-furan-2-one
  参考文献：
  名称：

  Nucleo-Palladation-Triggering Alkene Functionalization: A Route to γ-Lactones

  摘要：

  An unprecedented strategy for the highly effective synthesis of gamma-lactones from homoallylic alcohols was achieved by palladium catalysis in one step. The protocol affords aryl, alkyl, and spiro gamma-lactones directly from readily available "homoallylic alcohols in good yields with excellent functional group tolerance and high chemoselectivity under mild conditions.

  DOI：

  10.1021/acs.orglett.7b02688

文献信息

• (HMe2SiCH2)2: A Useful Reagent for B(C6F5)3-Catalyzed Reduction–Lactonization of Keto Acids: Concise Syntheses of (–)-cis-Whisky and (–)-cis-Cognac Lactones
  作者：Zhenlei Song、Hengmu Xie、Ji Lu、Yingying Gui、Lu Gao

  DOI：10.1055/s-0036-1588488

  日期：2017.11

  (HMe2SiCH2)2 has been utilized as a useful reagent for B(C6F5)3-catalyzed reduction–lactonization of keto acids to synthesize γ- and δ-lactones. The process led concisely to (–)-cis-whisky and (–)-cis-cognac lactones in respective overall yields of 32% and 36%.

  (HMe2SiCH2)2 已被用作 B(C6F5)3 催化的酮酸还原-内酯化合成γ-和δ-内酯的有用试剂。该过程简明地导致 (-)-cis-whisky 和 ​​(-)-cis-cognac 内酯的总产率分别为 32% 和 36%。
• Copper-Catalyzed Intermolecular Oxidative [3 + 2] Cycloaddition between Alkenes and Anhydrides: A New Synthetic Approach to γ-Lactones
  作者：Liangbin Huang、Huanfeng Jiang、Chaorong Qi、Xiaohang Liu

  DOI：10.1021/ja108073k

  日期：2010.12.22

  A new copper-catalyzed oxidative [3 + 2] cycloaddition of alkenes with anhydrides using oxygen as the sole oxidant to afford γ-lactones has been developed. This catalyzed cyclization process has a broad substrate scope and affords γ-lactones in good to excellent yields.

  已经开发了一种新的铜催化氧化 [3 + 2] 烯烃与酸酐的环加成反应，使用氧气作为唯一的氧化剂，得到 γ-内酯。这种催化环化过程具有广泛的底物范围，并以良好的收率提供 γ-内酯。
• γ-Substituted butyrolactones from acrolein and carbonyl compounds
  作者：José Barluenga、José R. Fernández、Miguel Yus

  DOI：10.1039/c39870001534

  日期：——

  The lithiation of 3-chloropropanal diethyl acetal (easily prepared from acrolein) at –78 °C with lithium naphthalenide followed by reaction with various carbonyl compounds, and final oxidation with m-chloroperbenzoic acid leads to γ-substituted butyrolactones.

  的锂化3- chloropropanal二乙基缩醛（容易从丙烯醛制备）在-78℃用锂萘基，随后通过与各种羰基化合物反应，并用最终的氧化米氯过苯甲酸导致γ取代的丁内酯。
• Dichotomous Reaction Pathways for the Oxidative Palladium(II)-Catalyzed Intramolecular Acyloxylation of Alkenes
  作者：Julie Oble、Giovanni Poli、Fadila Louafi、Mélanie Lorion

  DOI：10.1055/s-0035-1560071

  日期：——

  This work provides an in-depth investigation of the Pd(II)-catalyzed oxidative cyclization of various alkenoic acids bearing different tethers between the carboxylic acid moiety and the olefin function, showcasing how different mechanistic pathways (oxypalladation or allylic C-H activation) can be operative. The factors biasing toward one or the other of these reactivities are rationally discussed and compared with our recent studies on the Pd(II)-catalyzed intramolecular amination.
• Nucleo-Palladation-Triggering Alkene Functionalization: A Route to γ-Lactones
  作者：Meifang Zheng、Pengquan Chen、Liangbin Huang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.orglett.7b02688

  日期：2017.11.3

  An unprecedented strategy for the highly effective synthesis of gamma-lactones from homoallylic alcohols was achieved by palladium catalysis in one step. The protocol affords aryl, alkyl, and spiro gamma-lactones directly from readily available "homoallylic alcohols in good yields with excellent functional group tolerance and high chemoselectivity under mild conditions.