2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-tribenzyloxy-4H-chromen-4-one | 498548-14-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-tribenzyloxy-4H-chromen-4-one
• 英文别名: 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-tribenzyloxychromen-4-one；2-(2,2-Diphenyl-1,3-benzodioxol-5-yl)-3,5,7-tris(phenylmethoxy)chromen-4-one
• CAS: 498548-14-4
• 化学式: C₄₉H₃₆O₇
• 分子量: 736.821
• InChiKey: QWXNDRCQBALYFW-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  56
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-tribenzyloxy-4H-chromen-4-one 在 20 % Pd(OH)2/C 、 水 、 氢气 、 sodium methylate 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 绣线菊甙
  参考文献：
  名称：

  Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

  摘要：

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.03.110
• 作为产物：
  描述：

  二氯二苯甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.17h， 生成 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-tribenzyloxy-4H-chromen-4-one
  参考文献：
  名称：

  Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

  摘要：

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.03.110

文献信息

• 槲皮素衍生物及其制备方法和应用
  申请人：南京惠特莱医药科技有限公司

  公开号：CN104557891B

  公开（公告）日：2017-12-19

  本发明公开了一种槲皮素的衍生物及其制备方法和应用，该制备方法首先用二氯二苯基甲烷保护槲皮素邻二酚羟基，并结合苄基保护基，得到选择性保护的槲皮素衍生物，再分别单独与硫酸二甲酯、硫酸二乙酯、烯丙基溴、对甲苯磺酰氯和乙酸酐进行反应，生成相应的槲皮素衍生物。所制备的衍生化合物都表现出优于槲皮素的抑制NRK‑49F增殖活性。其中，甲基和对甲苯磺酰基复合取代的槲皮素衍生物20a‑1、14a‑2和23d‑1表现出更加优良的抑制NRK‑49F增殖活性，抑制率分别达到86.33%、78.04%、75.91%。可见，目前得到的槲皮素衍生化产物对肾成纤维细胞NRK‑49F增殖有明显的抑制作用。
• Hemisynthesis of all the O-monomethylated analogues of quercetin including the major metabolites, through selective protection of phenolic functions
  作者：Mohamed Bouktaib、Stéphane Lebrun、Aziz Atmani、Christian Rolando

  DOI：10.1016/s0040-4020(02)01306-6

  日期：2002.12

  A new methodology for the hemisynthesis of all the five O-monomethylated analogues of quercetin (3'-O-methylquercetin (isorhamnetin), 4'-O-methylquercetin (tamarixetin), 3-O-methylquercetin, 5-O-methylquercetin (azaleatin) and 7-O-methylquercetin (rhamnetin)) through sequential protection of the different phenolic functions of quercetin is reported. (C) 2002 Published by Elsevier Science Ltd.
• Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers
  作者：Mohammed Kajjout、Christian Rolando

  DOI：10.1016/j.tet.2011.03.110

  日期：2011.6

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.