7-methoxy-8-hydroxy-3-(3,4,5-trimethoxyphenyl)coumarin | 1187551-56-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-methoxy-8-hydroxy-3-(3,4,5-trimethoxyphenyl)coumarin
• 英文别名: 8-Hydroxy-7-methoxy-3-(3,4,5-trimethoxyphenyl)chromen-2-one
• CAS: 1187551-56-9
• 化学式: C₁₉H₁₈O₇
• 分子量: 358.348
• InChiKey: BAWXVEUBDJTLQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-methoxy-8-hydroxy-3-(3,4,5-trimethoxyphenyl)coumarin 在 potassium hydroxide 作用下， 以 1,2-丙二醇 为溶剂， 反应 0.5h， 以54%的产率得到E-2,3-dihydroxy-3’,4,4’,5’-tetramethoxystilbene
  参考文献：
  名称：

  α，β-不饱和芳族内酯的脱羧作用：由3-芳基香豆素或异金龙酮合成E-邻-羟基对苯二酚

  摘要：

  已经建立了一种简单且对环境友好的策略，用于合成E-邻-羟基对苯二酚。两种α，β不饱和芳族内酯，的即3-arylcoumarins和isoaurones，既可以容易地进行在KOH的存在下水解级联/脱羧反应在乙二醇，得到期望的E-邻-hydroxystilbenes在中度至高产。

  DOI：

  10.1039/c7gc02994b
• 作为产物：
  描述：

  (l)-3-(3',4',5'-trimethoxyphenyl)-7-methoxy-8-ethanoyloxycoumarin 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以95%的产率得到7-methoxy-8-hydroxy-3-(3,4,5-trimethoxyphenyl)coumarin
  参考文献：
  名称：

  Hydroxyl Substitutional Effect on Selective Synthesis of cis, trans Stilbenes and 3-Arylcoumarins Through Perkin Condensation

  摘要：

  The substitutional effect in the selective synthesis of cis, trans stilbenes and 3-arylcoumarins has been described. The regio- and geometrical selectivity for synthesis of stilbene derivatives under the Perkin strategy strongly depends on the presence or absence of hydroxyl group as well as their positions in the phenyl ring. As a result, practical synthetic strategies were established for preparing various natural stilbenes including combretastatin A-4, pterostilbene, and resveratrol with satisfactory yields (49.2-63.7%).

  DOI：

  10.1080/00397911.2010.538889

文献信息

• 一种3-芳基香豆素类衍生物及其制备方法和用途
  申请人：中山大学

  公开号：CN113121485B

  公开（公告）日：2023-01-03

  本发明公开了一种3‑芳基香豆素类衍生物及其制备方法和用途，是以取代苯乙酸和取代2‑羟基苯甲醛为原料，在三乙胺和乙酸酐存在下，发生串联的缩合‑内酯化反应，反应完毕后，再各自独立地经三种后处理方法得到3‑芳基香豆素类衍生物。本发明提供的3‑芳基香豆素类衍生物对SIRT3蛋白具有良好的亲和力，并能上调SIRT3蛋白的去乙酰化酶活性，逆转ISO(异丙肾上腺素)刺激诱导的心肌肥厚，可用于制备抗心血管疾病或抗糖尿病药物。
• Decarboxylation of α,β-unsaturated aromatic lactones: synthesis of<i>E-ortho</i>-hydroxystilbenes from 3-arylcoumarins or isoaurones
  作者：Xihua Huang、Jie Liu、Jianfei Sheng、Xianheng Song、Zhibo Du、Mingkang Li、Xuejing Zhang、Yong Zou

  DOI：10.1039/c7gc02994b

  日期：——

  A simple and environmentally friendly strategy for the synthesis of E-ortho-hydroxystilbenes has been established. Two kinds of α,β-unsaturated aromatic lactones, i.e. the 3-arylcoumarins and the isoaurones, could both readily undergo a cascade hydrolyzation/decarboxylation reaction in the presence of KOH in ethylene glycol to afford the desired E-ortho-hydroxystilbenes in moderate to high yields.

  已经建立了一种简单且对环境友好的策略，用于合成E-邻-羟基对苯二酚。两种α，β不饱和芳族内酯，的即3-arylcoumarins和isoaurones，既可以容易地进行在KOH的存在下水解级联/脱羧反应在乙二醇，得到期望的E-邻-hydroxystilbenes在中度至高产。
• Hydroxyl Substitutional Effect on Selective Synthesis of <i>cis, trans</i> Stilbenes and 3-Arylcoumarins Through Perkin Condensation
  作者：Chun-Fen Xiao、Yong Zou、Jian-Li Du、Hong-Yi Sun、Xian-Ke Liu

  DOI：10.1080/00397911.2010.538889

  日期：2012.5.1

  The substitutional effect in the selective synthesis of cis, trans stilbenes and 3-arylcoumarins has been described. The regio- and geometrical selectivity for synthesis of stilbene derivatives under the Perkin strategy strongly depends on the presence or absence of hydroxyl group as well as their positions in the phenyl ring. As a result, practical synthetic strategies were established for preparing various natural stilbenes including combretastatin A-4, pterostilbene, and resveratrol with satisfactory yields (49.2-63.7%).