7-hydroxy-2,2-dimethyl-8-(2-methylbut-3-en-2-yl)-5-phenethyl-4H-benzo[d][1,3]dioxin-4-one | 1353896-17-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 7-hydroxy-2,2-dimethyl-8-(2-methylbut-3-en-2-yl)-5-phenethyl-4H-benzo[d][1,3]dioxin-4-one
• CAS: 1353896-17-9
• 化学式: C₂₃H₂₆O₄
• 分子量: 366.457
• InChiKey: RENWWHZVFWTNKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  6-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-7,7-dimethyl-1-phenylnon-8-ene-3,5-dione 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以68%的产率得到7-hydroxy-2,2-dimethyl-8-(2-methylbut-3-en-2-yl)-5-phenethyl-4H-benzo[d][1,3]dioxin-4-one
  参考文献：
  名称：

  Total synthesis of amorfrutin A via a palladium-catalyzed migratory prenylation–aromatization sequence

  摘要：

  The total synthesis of amorfrutin A, a prenyl bibenzyl natural product has been achieved in five steps from 2,2,6-trimethyl-4H-1,3-dioxin-4-one. The key step of the synthesis is an efficient palladium(0)-catalyzed decarboxylative prenylation migration and aromatization sequence. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.019

文献信息

• Mechanistic studies of highly regioselective decarboxylative-prenyl migration reactions of prenyloxycarbonyl-diketo-dioxinones
  作者：Katie Anderson、Sylvain Laclef、Anthony G.M. Barrett

  DOI：10.1016/j.tet.2014.06.098

  日期：2014.9

  Mechanistic studies of tandem regioselective decarboxylation, prenyl transfer, and aromatization reactions of prenyl dioxinone diketo-carboxylates to provide 3-prenyl-resorcylate derivatives are described. Studies of the effects of concentration and the base employed as well as the results of cross-over experiments were all found to be consistent with the reaction proceeding largely via an intermolecular

  描述了串联的区域选择性脱羧，异戊二烯基转移和异戊二烯二酮二酮羧酸酯提供3-异戊烯基-间苯二酸酯衍生物的芳构化反应的机理研究。发现对浓度和所用碱的影响的研究以及交叉实验的结果均与很大程度上通过分子间反应途径进行的反应一致。