3,3-spirocyclopentenyldihydrofuran-2,4-diones | 848127-74-2

• 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-spirocyclopentenyldihydrofuran-2,4-diones
• 英文别名: 2-oxa-spiro[4.4]non-7-ene-1,4-dione；2-Oxaspiro[4.4]non-7-ene-1,4-dione；2-oxaspiro[4.4]non-7-ene-1,4-dione
• CAS: 848127-74-2
• 化学式: C₈H₈O₃
• 分子量: 152.15
• InChiKey: ILTFHBISYXLSRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 3,3-spirocyclopentenyldihydrofuran-2,4-diones 以 甲苯 为溶剂， 反应 72.0h， 以50%的产率得到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：

  3,3-diallyldihydrofuran-2,4-dione 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 以69%的产率得到3,3-spirocyclopentenyldihydrofuran-2,4-diones
  参考文献：
  名称：

  Spiro-annulation of barbituric acid derivatives and its analogs by ring-closing metathesis reaction

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2004.12.034

文献信息

• 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：——