3,3-diallyldihydrofuran-2,4-dione | 124706-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3,3-diallyldihydrofuran-2,4-dione
• 英文别名: 3,3-diallylfuran-(2H)-2,4-dione；3,3-diallyl-furan-2,4-dione；3,3-Bis(prop-2-enyl)oxolane-2,4-dione
• CAS: 124706-41-8
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: QHDFICYMOSEKSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-diallyldihydrofuran-2,4-dione 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 116.0h， 生成 7,12-Dioxa-dispiro[4.0.5.3]tetradeca-2,8-diene-10,14-dione
  参考文献：
  名称：

  Annulated butanolides by ring closing metathesis of diallyltetronic acid derivatives

  摘要：

  3,3-Diallyldihydrofuran-2,4-diones 5 with two identical allyl residues were obtained by Tsuji-Trost-type Pd-catalysed allylation of either 4-O-allyltetronates or 3-allyltetronic acids. Allylation of sodium 3-allyltetronate with a second allyl acetate gave mixed derivatives 5 as did the Claisen rearrangement of 4-O-allyl 3-allyltetronates 6 under microwave conditions. Compounds 5 and 6 were converted to butanolides with 3,3-spirocyclopentenyl or 3,4-cycloalkanyl annulation by ring closing metathesis with Grubbs catalysts. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.152
• 作为产物：
  描述：

  4-O-allyl-3-allyltetronate 在 silica gel 作用下， 反应 0.12h， 以75%的产率得到3,3-diallyldihydrofuran-2,4-dione
  参考文献：
  名称：

  硅胶支持物上的微波辅助克莱森重排

  摘要：

  已经开发了一种快速，高效且对环境无害的无溶剂程序，用于在硅胶载体上进行微波辅助的克莱森重排。使用该方案制备了各种双烯丙基酮。

  DOI：

  10.1016/j.tetlet.2004.11.012

文献信息

• A Regioselective Tsuji-Trost Pentadienylation of 3-Allyltetronic Acid
  作者：Rainer Schobert、Bertram Barnickel

  DOI：10.1055/s-0029-1216898

  日期：——

  π-system. This carbonate reacted fast enough to avoid scrambling and formation of symmetric bisallyl tetronic acids. The 3-allyl-3-penta-2,4-dienyltetronic acid thus obtained is a key intermediate en route to the natural spirolactone bakkenolide A. allylation - regioselectivity - palladium - tetronic acid - Schlosser-Wittig reaction

  开发了3-烯丙基-四氢磺酸钠与甲基5-三甲基甲硅烷基戊-2,4-二烯基碳酸酯的区域选择性Tsuji-Trost反应。通过在π系统的远端引入易于除去的SiMe 3屏蔽基团，可以在戊二烯基残基的更高度取代的末端形成碳-碳键。该碳酸盐反应足够快，以避免加扰和形成对称的双烯丙基tetronic酸。如此获得的3-烯丙基-3-戊-2,4-二烯基tetronic酸是通往天然螺内酯bakkenolide A的关键中间体。 烯丙基化-区域选择性-钯-十四酸-Schlosser-Wittig反应
• Microwave-assisted Claisen rearrangement on a silica gel support
  作者：Sambasivarao Kotha、Kalyaneswar Mandal、Ashoke Chandra Deb、Shaibal Banerjee

  DOI：10.1016/j.tetlet.2004.11.012

  日期：2004.12

  A fast, efficient and environmentally benign solvent-free procedure has been developed for microwave-assisted Claisen rearrangement on a silica gel support. Various bis-allyl ketones were prepared using this protocol.

  已经开发了一种快速，高效且对环境无害的无溶剂程序，用于在硅胶载体上进行微波辅助的克莱森重排。使用该方案制备了各种双烯丙基酮。
• Spiro-annulation of barbituric acid derivatives and its analogs by ring-closing metathesis reaction
  作者：Sambasivarao Kotha、Ashoke Chandra Deb、Ramanatham Vinod Kumar

  DOI：10.1016/j.bmcl.2004.12.034

  日期：2005.2

  Barbituric acid 1 and related beta-dicarbonyl compounds were dialkenylated under the phase-transfer catalyst [e.g,, benzyltriethylammonium chloride (BTEAC)] conditions to generate the diallylated products. These diallylated products were subjected to the ring-closing metathesis (RCM) reaction to deliver the corresponding spiro-annulated derivatives. (C) 2005 Elsevier Ltd. All rights reserved.
• Annulated butanolides by ring closing metathesis of diallyltetronic acid derivatives
  作者：Rainer Schobert、Juan Manuel Urbina-González

  DOI：10.1016/j.tetlet.2005.03.152

  日期：2005.5

  3,3-Diallyldihydrofuran-2,4-diones 5 with two identical allyl residues were obtained by Tsuji-Trost-type Pd-catalysed allylation of either 4-O-allyltetronates or 3-allyltetronic acids. Allylation of sodium 3-allyltetronate with a second allyl acetate gave mixed derivatives 5 as did the Claisen rearrangement of 4-O-allyl 3-allyltetronates 6 under microwave conditions. Compounds 5 and 6 were converted to butanolides with 3,3-spirocyclopentenyl or 3,4-cycloalkanyl annulation by ring closing metathesis with Grubbs catalysts. (c) 2005 Elsevier Ltd. All rights reserved.
• Kotha, Sambasivarao; Deb, Ashoke Chandra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 7, p. 1120 - 1134
  作者：Kotha, Sambasivarao、Deb, Ashoke Chandra

  DOI：——

  日期：——