3,3-dicinnamyl-3H,5H-furan-2,4-dione | 115580-38-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3,3-dicinnamyl-3H,5H-furan-2,4-dione
• 英文别名: 3,3-bis[(E)-3-phenylprop-2-enyl]oxolane-2,4-dione
• CAS: 115580-38-6
• 化学式: C₂₂H₂₀O₃
• 分子量: 332.399
• InChiKey: BEOKVXYPFFZFAM-FNCQTZNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基-2(5H)-呋喃酮 、 3-苯基丙-2-烯-1-醇 在 palladium diacetate 1-金刚烷甲酸 、 三苯基膦 作用下， 以 水 为溶剂， 反应 0.25h， 以98%的产率得到3,3-dicinnamyl-3H,5H-furan-2,4-dione
  参考文献：
  名称：

  Direct palladium/carboxylic acid-catalyzed C-allylation of cyclic 1,3-diones with allylic alcohols in water

  摘要：

  The direct activation of C-O bonds in allylic alcohols in water as a suspension medium by palladium complexes has been accelerated by carrying out the reactions in the presence of a carboxylic acid. The palladium-catalyzed allylation of cyclic 1,3-diones using allylic alcohols directly gave the corresponding C-allylated products in good yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.082

文献信息

• Palladium catalyzed c-allylation of highly acidic carbo and heterocyclic β-dicarbonyl compounds
  作者：M. Prat、M. Moreno-Mañas、J. Ribas

  DOI：10.1016/s0040-4020(01)86091-9

  日期：1988.1

  Highly acidic carbo and heterocyclic β-dicarbonyl compounds such as barbituric acid, 3,5-dimethyl-2-1,2,6-thiadiazine 1,1-dioxide, cyclohexane-1,3-dione, tetronic acids, Meldrum acid and 1,2-diphenylpyrazolidine-3,5-dione are efficiently C-allylated with primary and secondary allylating agents under palladium catalysis.

  高酸性碳和杂环β-二羰基化合物，例如巴比妥酸，3,5-二甲基-2 -1,2,6-噻二嗪1,1-二氧化物，环己烷-1,3-二酮，四氢代酸，Meldrum酸和1在钯催化下，用伯和仲烯丙基化剂有效地将2--二苯基吡唑烷-3,5-二酮进行C-烯丙基化。
• Palladium catalyzed allylic C-alkylation of highly acidic and enolic heterocyclic substrates: tetronic acid and triacetic acid lactone
  作者：Marcial Moreno-Mañas、Maria Prat、Jordi Ribas、Albert Virgili

  DOI：10.1016/s0040-4039(00)80156-2

  日期：——

  Tetronic acid (pKa 3.76) and triacetic acid lactone (pKa 4.94) have been alkylated at their active carbon atoms by means of thermodinamically controlled palladium catalyzed allylic alkylations.

  已通过热丁二胺控制的钯催化的烯丙基烷基化作用将四氢苯甲酸（pK a 3.76）和三乙酸内酯（pK a 4.94）烷基化。
• 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.