2(5H)-Furanone, 5-phenyl-3-propyl- | 336800-60-3

• 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: 2(5H)-Furanone, 5-phenyl-3-propyl-
• 英文别名: 2-phenyl-4-propyl-2H-furan-5-one
• CAS: 336800-60-3
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: SFTWRWFUJKIRMW-UHFFFAOYSA-N

物化性质

• 沸点：
  363.5±31.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  4-phenyl-2-propyl-2,3-butadienoic acid 在 palladium dichloride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.5h， 以76%的产率得到2(5H)-Furanone, 5-phenyl-3-propyl-
  参考文献：
  名称：

  Efficient Synthesis of Bibutenolide Derivatives through Oxidative Dimeric Cyclization−Coupling Reaction of 2,3-Allenoic Acids

  摘要：

  [GRAPHICS]An oxidative coupling-dimerization reaction of 2,3-allenoic acids was observed to provide an efficient route to bibutenolide derivatives, which are not readily available. A, new system (PdCl2/Rl/air) for regeneration of the palladium(II) catalyst was also established.

  DOI：

  10.1021/ol0342812

文献信息

• Efficient Synthesis of 4-(3′-Furanyl)butenolide Derivatives via PdII-Catalyzed Oxidative Heterodimeric Cyclization Reaction of 2,3-Allenoic Acids and 1,2-Allenyl Ketones
  作者：Shengming Ma、Zhanqian Yu

  DOI：10.1002/chem.200305341

  日期：2004.4.19

  conveniently through chiral resolution with optically active amines, that is, cinchonidine or alpha-methyl benzylamine. A mechanistic study showed that the reaction proceeded via a matched double oxypalladation-reductive elimination process. The Pd(II) species may be regenerated via the subsequent cyclometallation of two equivalents of 1,2-allenyl ketones with Pd(0) and protonlysis of Pd enolates formed with the

  据报道，具有不同官能度的两类丙二烯之间的氧化环化/二聚反应为多取代的4-（3'-呋喃基）-2（5H）-呋喃酮提供了一条有效的途径，而该方法无法从已知方法中轻易获得。旋光性高的丁烯化物可以很容易地由旋光性的2，3-烯丙酸形成，这可以通过旋光拆分与旋光性胺，即辛可尼丁或α-甲基苄基胺方便地获得。机理研究表明，该反应通过匹配的双氧钯还原-还原消除过程进行。可以通过随后的两个当量的1,2-烯基酮与Pd（0）的环金属化作用以及由原位生成的HCl形成的Pd烯醇化物的质子化来再生Pd（II）物种。
• PdII-Catalyzed Oxidative Dimeric Cyclization-Coupling Reaction of 2,3-Allenoic Acids: An Efficient Synthesis of Bibutenolide Derivatives
  作者：Shengming Ma、Zhanqian Yu、Zhenhua Gu

  DOI：10.1002/chem.200401079

  日期：2005.4.8

  active bibutenolides in high yields and ee. Based on a mechanistic study, it is believed that the reaction may proceed by means of a double oxypalladation and reductive elimination to yield butenolide 3 and Pd(0) species, which may be reoxidized to the catalytically active Pd(II) species in the presence of alkyl iodide/air, metallic iodide/air, or benzoquinone.

  已经开发了三套方便的催化体系，用于Pd（II）催化的不同取代的2,3-烯丙酸的氧化二聚环化偶联，提供了双丁烯内酯，否则它们是不容易获得的。讨论了这些系统的优缺点。尽管对于外消旋2，3-烯丙酸的双环化的非对映选择性低，但是在旋光性2，3-烯丙酸的双环化反应中实现了优异的非对映选择性，从而以高收率和ee产生了旋光性丁二烯内酯。根据机理研究，我们认为该反应可以通过双重的氧化钯和还原消除反应进行，从而生成丁烯内酯3和Pd（0）物种，
• Photocatalytic Chemoselective Cyclic Oxysulfonylation of 2,3-Allenoic Acids
  作者：Yaqi Shi、Chunling Fu、Jian Zheng、Shengming Ma

  DOI：10.1021/acs.orglett.4c01730

  日期：2024.6.21

  Photoinduced cyclization of 2,3-allenoic acids with sulfonyl chloride providing an efficient synthesis of 4-sulfonylated furan-2(5H)-ones under mild reaction conditions has been achieved. The reaction enjoys a high chemoselectivity and tolerates a wide range of functional groups. The catalytic cycle has been validated through control experiments, cyclic voltammetry studies, and Stern–Volmer quenching

  已经实现了 2,3-联烯酸与磺酰氯的光诱导环化，从而在温和的反应条件下有效合成了 4-磺酰化呋喃-2(5 H )-酮。该反应具有较高的化学选择性并能耐受多种官能团。催化循环已通过对照实验、循环伏安研究和 Stern-Volmer 猝灭研究得到验证。
• CuCl-Catalyzed cycloisomerization reaction of 1,2-allenyl carboxylic acids. A cost-effective synthesis of β-unsubstituted butenolides
  作者：Shengming Ma、Zhanqian Yu、Shulin Wu

  DOI：10.1016/s0040-4020(00)01149-2

  日期：2001.2

  Fourteen examples of 2,3-butadienoic acids were synthesized according to the known procedures and their high-yielding CuCl-catalyzed cycloisomerization reaction to afford butenolides were described. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Pd(OAc)₂-Catalyzed Cyclization of 2,3-Allenoic Acids in the Presence of Terminal α,β-Unsaturated Alkynones: A One-Pot Highly Stereoselective Synthesis of 4-(3′-Oxo-1′(<i>E</i>)-alkenyl)-2(5<i>H</i>)-furanones
  作者：Guofei Chen、Rong Zeng、Zhenhua Gu、Chunling Fu、Shengming Ma

  DOI：10.1021/ol801610w

  日期：2008.10.2

  The Pd(OAc)(2)-catalyzed cyclization reaction of 2,3-allenoic acids in the presence of terminal alpha,beta-unsaturated alkynones afforded an E/Z mixture of 4-(3'-oxo-1'-alkenyl)-2(5H)-furanones. A subsequent complete isomerization of the Z-isomer to E-isomer was observed in DMSO at 90 degrees C, which led to a highly stereoselective synthesis of 4-(3'-oxo-1'(E)-alkenyl)-2(5H)-furanones. A possible mechanism is proposed.