4-(4-hydroxyphenyl)-dihydrofuran-2-one | 133570-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(4-hydroxyphenyl)-dihydrofuran-2-one
• 英文别名: 4-(4-hydroxyphenyl)dihydrofuran-2-one；4-(4-Hydroxyphenyl)oxolan-2-one；4-(4-hydroxyphenyl)oxolan-2-one
• CAS: 133570-40-8
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: LJLFQZPKDYLXPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-hydroxyphenyl)-dihydrofuran-2-one 在 aluminum (III) chloride 、 caesium carbonate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 1.09h， 生成 4-Hydroxy-1-morpholin-4-yl-3-(4-phenylmethoxyphenyl)butan-1-one
  参考文献：
  名称：

  Beyond the affinity for protein kinase C: exploring 2-phenyl-3-hydroxypropyl pivalate analogues as C1 domain-targeting ligands

  摘要：

  在过去的十五年中，我们报道了针对蛋白激酶C（PKC）的C1结构域的不同系列化合物的设计和合成，这些化合物基于各种模板。

  DOI：

  10.1039/c4md00564c
• 作为产物：
  描述：

  4-(4-Hydroxyphenyl)oxolan-2-ol 在 Celite 、 silver carbonate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以60%的产率得到4-(4-hydroxyphenyl)-dihydrofuran-2-one
  参考文献：
  名称：

  β-Vinyl-γ-butyrolactones via the palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol

  摘要：

  The palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol affords beta-vinyl-gamma-butyrolactols (4-vinyl-2-hydroxy-tetrahydrofurans) which are converted into the corresponding beta-vinyl-gamma-butyrolactones by a smooth oxidation with Ag2CO3 on celite. Preparation of beta-substituted-gamma-butyrolactones can be performed without the isolation of the intermediate gamma-butyrolactols, thus simplifying the procedure and usually with higher overall yields. The outcome of the palladium-catalysed formation of beta-substituted-gamma-butyrolactols strongly depends on the nature of the added base. Best results are obtained by using NaHCO3 or K2CO3 in the presence of n-Bu4NCl or TEBA.

  DOI：

  10.1016/s0040-4020(01)86427-9

文献信息

• Benzyl (Phenyl) γ- and δ-lactones via Photoinduced Tandem Ar−C, C−O Bond Formation
  作者：Stefano Protti、Maurizio Fagnoni、Angelo Albini

  DOI：10.1021/ja0627287

  日期：2006.8.1

  A convenient metal-free procedure for the preparation of benzyl (phenyl) gamma- and delta-lactones is illustrated. This method is based on the photochemical generation of phenyl cations and their reaction with 3, 4, or 5-alkenoic acids. This leads to a phenyl- or benzyl-substituted lactone by tandem formation of an aryl-C and C-O bond. The intermediacy of a phenonium ion imparts a full regio- and stereoselectivity to the reaction.