5-(3',4'-bis(benzyloxy)benzylidene)furan-2(5H)-one | 1257063-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(3',4'-bis(benzyloxy)benzylidene)furan-2(5H)-one
• 英文别名: 5-[3,4-bis(benzyloxy)benzylidene]furan-2(5H)-one；(5Z)-5-[[3,4-bis(phenylmethoxy)phenyl]methylidene]furan-2-one
• CAS: 1257063-78-7
• 化学式: C₂₅H₂₀O₄
• 分子量: 384.431
• InChiKey: SQQCABKKADLESS-JCMHNJIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 、 2(5H)-呋喃酮 在 叔丁基二甲硅基三氟甲磺酸酯 、 N,N-二异丙基乙胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-(3',4'-bis(benzyloxy)benzylidene)furan-2(5H)-one 、 5-(3',4'-bis(benzyloxy)benzylidene)furan-2(5H)-one
  参考文献：
  名称：

  表儿茶素的环裂代谢产物的简明合成：5-(3,4-Dihydroxybenzyl)dihydrofuran-2(3H)-one M6

  摘要：

  表儿茶素、5-(3,4-二羟基苄基)二氢呋喃-2(3H)-one M6 和 3-甲基化 M6 的裂环代谢物是由 3,4-二羟基苯甲醛和呋喃-2(5H)-one 制备的两种新的简洁方法，产量极佳（三到两步，总产量为 40-60%）。

  DOI：

  10.1080/00397910903419845

文献信息

• Profiling Vaccinium macrocarpon components and metabolites in human urine and the urine ex-vivo effect on Candida albicans adhesion and biofilm-formation
  作者：Giovanna Baron、Alessandra Altomare、Luca Regazzoni、Laura Fumagalli、Angelica Artasensi、Elisa Borghi、Emerenziana Ottaviano、Cristian Del Bo、Patrizia Riso、Pietro Allegrini、Giovanna Petrangolini、Paolo Morazzoni、Antonella Riva、Lolita Arnoldi、Marina Carini、Giancarlo Aldini

  DOI：10.1016/j.bcp.2019.113726

  日期：2020.3

  The aim of this work was to profile, by using an HPLC-MS/MS method, cranberry compounds and metabolites found in human urine after ingestion of a highly standardized cranberry extract (Anthocran (R)). Two different strategies were adopted for the data analysis: a targeted and an untargeted approach. These strategies allowed the identification of 42 analytes including cranberry components, known metabolites and metabolites hitherto unreported in the literature, including six valerolactones/valeric acid derivatives whose presence in urine after cranberry consumption has never been described before. Absolute concentrations of 26 over 42 metabolites were obtained by using pure available standards. Urine collected at different time points after the last dosage of Anthocran (R) were tested on the reference strain C. albicans SC5314, a biofilm-forming strain. Fractions collected after 12 h were found to significantly reduce the adhesion and biofilm formation compared to the control (p < 0.05). A similar effect was then obtained by using Anthocran (TM) Phytosome (TM), the lecithin formulation containing 1/3 of standardized cranberry extract and formulated to enhance the absorption of the cranberry components. The urinary profile of cranberry components and metabolites in the urine fractions collected at 1 h, 6 h and 12 h after the last capsule intake were then reproduced by using the pure standards at the concentration ranges found in the urine fraction, and tested on C. albicans. Only the mixture mimicking the urinary fraction collected at 12 h and containing as main components, quercetin and 5-(3',4'-dihydroxyphenyl)-gamma-valerolactone was found effective thus confirming the ex-vivo results.
• Concise Synthesis of Ring-Fission Metabolites of Epicatechin: 5-(3,4-Dihydroxybenzyl)dihydrofuran-2(3<i>H</i>)-one M6
  作者：Xiaowei Chang、Weimin Peng、Yin-Fang Yao、Jan Koek

  DOI：10.1080/00397910903419845

  日期：2010.10.20

  The ring-fission metabolites of epicatechin, 5-(3,4-dihydroxybenzyl)dihydrofuran-2(3H)-one M6 and 3-methylated M6, were prepared from 3,4-dihydroxybenzaldehyde and furan-2(5H)-one using two new concise methods in excellent yields (three or two steps in 40–60% overall yield).

  表儿茶素、5-(3,4-二羟基苄基)二氢呋喃-2(3H)-one M6 和 3-甲基化 M6 的裂环代谢物是由 3,4-二羟基苯甲醛和呋喃-2(5H)-one 制备的两种新的简洁方法，产量极佳（三到两步，总产量为 40-60%）。