diallyl-5,5 (5H)furannone-2 | 72081-14-2

• 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: diallyl-5,5 (5H)furannone-2
• 英文别名: 5,5-diallyl-5H-furan-2-one；3,3-diallyl-butenolide；5,5-diallyl-(5H)-furan-2-one；5,5-Bis(prop-2-enyl)furan-2-one
• CAS: 72081-14-2
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: FBRZLTBIWKRLTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  diallyl-5,5 (5H)furannone-2 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到1-oxa-spiro[4.4]non-3,7-dien-2-one
  参考文献：
  名称：

  The Synthesis of Spirolactones Using Indium-Mediated Allylation of Cyclic Anhydrides and Ring-Closing Olefin Metathesis

  摘要：

  以环状酸酐为原料，通过铟介导的烯丙基化反应和闭环烯烃偏聚（RCM）反应等关键步骤制备出多种螺内酯。

  DOI：

  10.1055/s-2001-18084
• 作为产物：
  描述：

  diallyl-5,5 dioxa-4,10 exo-tricyclo<5.2.1.0^2.6>decene-8 one-3 以95%的产率得到diallyl-5,5 (5H)furannone-2
  参考文献：
  名称：

  Etude de l'action des alkylmagnesiens primaires et arylmagnesiens sur les anhydrides tricycliques pontes

  摘要：

  DOI：

  10.1016/s0040-4020(01)91134-2

文献信息

• Diastereoselective ruthenium-catalysed cycloisomerisation of diallyllactones: preparation of exo-methylene spirolactones
  作者：Mathieu Michaut、Maurice Santelli、Jean-Luc Parrain

  DOI：10.1016/s0040-4039(03)00144-8

  日期：2003.3

  Diallyllactones (obtained from cyclic anhydrides via a double allylation reaction promoted by titanium tetrachloride) were cycloisomerised using 5 mol% of cyclooctadienyl ruthenium dichloride in ethanol providing the corresponding exomethylene spirolactones in good yields, with moderated to good diastereomeric excess.

  使用5摩尔％的环辛二烯基二氯化钌在乙醇中的环异构化二烯丙基内酯（通过四氯化钛促进的双烯丙基化反应从环状酸酐中获得），以适当的收率提供适度至良好的非对映异构体过量的相应的外亚甲基螺内酯。
• One-pot synthesis of α,β-butenolides from methyl (Z)-3-chloroacrylate
  作者：José Barluenga、José R. Fernández、Miguel Yus

  DOI：10.1039/c39860000183

  日期：——

  A one-pot synthesis of 4,4-disubstituted α,β-butenolides from methyl (Z)-3-chloroacrylate by successive addition of a Grignard reagent, lithiation, and carbonation is described.

  描述了通过连续添加格氏试剂，锂化和碳酸化由（Z）-3-氯丙烯酸甲酯一锅合成4,4-二取代的α，β-丁烯内酯。
• Preparation and some reactions of allylic indium reagents
  作者：Shuki Araki、Toshio Shimizu、Perminder S. Johar、Shun Ji Jin、Yasuo Butsugan

  DOI：10.1021/jo00007a050

  日期：1991.3

  A variety of allylic indium sesquihalides were readily prepared by the reaction of indium powder with allylic halides in DMF at room temperature. Protonation of the allylindium reagents proceeded regiospecifically at the gamma-position of the allylic group to give 1-propenes. A facile transformation of alpha-pinene to beta-pinene was achieved via a myrtenylindium intermediate. Oxygenation of the allylic indium reagents gave mixtures of allylic alcohol isomers in moderate yields. The coupling of the allylindium reagents with cyclic imides gave diverse products depending on the structures of the substrates and the reagents. Stannylation with tributylchlorostanane occurred exclusively at the alpha-carbon, yielding allytributylstannanes; E, Z isomerization of the allylic double bond depended largely upon the substitution pattern on the allylic moiety.
• Efficient synthesis of spirolactones from cyclic anhydrides via an allylation/alkylation-RCM sequence
  作者：Mathieu Michaut、Maurice Santelli*、Jean-Luc Parrain*

  DOI：10.1016/s0022-328x(00)00330-2

  日期：2000.7

  Starting from cyclic anhydrides the diallyl or dibutenyl lactones were obtained. The ring closing metathesis reaction of these using the Grubbs catalyst provided the corresponding spirolactones in good yields. With diallyl delta-lactone 2h, RCM occurred only in the presence of titanium tetraisopropoxide. (C) 2000 Elsevier Science S.A. All rights reserved.
• Indium-induced allylation of acid anhydrides
  作者：Shuki Araki、Nobuhito Katsumura、Hirokazu Ito、Yasuo Butsugan

  DOI：10.1016/s0040-4039(00)99525-x

  日期：1989.1