4-hydroxy-5,6,7-trimethoxycoumarin | 68061-76-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-hydroxy-5,6,7-trimethoxycoumarin
• 英文别名: 4-Hydroxy-5,6,7-trimethoxychromen-2-one
• CAS: 68061-76-7
• 化学式: C₁₂H₁₂O₆
• 分子量: 252.224
• InChiKey: IPYOTHOGJCBMCO-UHFFFAOYSA-N

物化性质

• 沸点：
  452.6±45.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5,6,7-trimethoxycoumarin 在 mercury(II) diacetate lead(IV) acetate 、 盐酸 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 3.0h， 生成 9-hydroxy-2,3,4,8-tetramethoxy-6H,11H-[2]benzopyrano[4,4-c][1]benzopyran-11-one
  参考文献：
  名称：

  Cascade Synthesis of Polyoxygenated 6H,11H-[2]Benzopyrano-[4,3-c][1]benzopyran-11-ones

  摘要：

  2-(Methoxymethoxymethyl)aryllead triacetates, obtained in situ from the corresponding arylboronic acids, reacted with 4-hydroxycoumarins, leading to 3-(2-methoxymethoxymethyl)aryl-4-hydroxycoumarin derivatives in good to high yields. These compounds underwent a cascade sequence of reactions, deprotection-halogenation-annulation, to afford polyoxygenated tetracyclic 6H,11H-[2]benzopyrano-[4,3-c] [1]benzopyran-11-ones in good yields. Some compounds showed a moderate cytotoxicity against human epithelial mammary HBL100 cells.

  DOI：

  10.1021/jo062592v
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 三氟化硼乙醚 、 sodium acetate 、 sodium hydride 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 生成 4-hydroxy-5,6,7-trimethoxycoumarin
  参考文献：
  名称：

  Combes; Finet; Siri, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 1, p. 38 - 44

  摘要：

  DOI：

文献信息

• Novel water-soluble anticancer agents derived from 4-arylcoumarins
  作者：Yu. B. Malysheva、Yu. V. Voitovich、E. A. Sharonova、S. Combes、E. V. Svirshchevskaya、E. L. Vodovozova、A. Yu. Fedorov

  DOI：10.1007/s11172-013-0149-3

  日期：2013.4

  Novel 4-arylcoumarin derivatives were obtained. They are water-soluble analogs of the well-known anticancer drug combretastatin A-4. The key step of the synthesis involves the Suzuki-Miyaura cross-coupling. The water-soluble salts obtained exhibit considerable cytotoxic activity against the HBL-100 and HaCaT cell lines.

  获得了新的 4-芳基香豆素衍生物。它们是众所周知的抗癌药物考布他汀 A-4 的水溶性类似物。合成的关键步骤涉及 Suzuki-Miyaura 交叉偶联。获得的水溶性盐对 HBL-100 和 HaCaT 细胞系表现出相当大的细胞毒活性。
• Reductive coupling of polyfunctionalized organobismuth and organolead arylating reagents in the synthesis of benzopyran derivatives
  作者：A. Yu. Fedorov、J. -P. Finet、O. G. Ganina、M. I. Naumov、A. S. Shavyrin

  DOI：10.1007/s11172-006-0163-9

  日期：2005.11

  Benzopyran derivatives were synthesized in good yields by the reactions of tris[2-(chloromethyl)phenyl]bismuth diacetate and 2-(halomethyl)aryllead triacetates with phenols and naturally occurring 4-hydroxycoumarins in the presence of bases according to a three-step one-pot procedure.

  苯并吡喃衍生物是通过三[2-(氯甲基)苯基]二乙酸铋和2-(卤甲基)芳基三乙酸铅与酚类和天然存在的4-羟基香豆素在碱存在下根据三步反应合成的- 锅程序。
• Use of 2-(methoxycarbonyl)phenyllead triacetate in lactone synthesis
  作者：B. A. Maryasin、A. S. Shavyrin、J.-P. Finet、A. Yu. Fedorov

  DOI：10.1007/s11172-006-0462-1

  日期：2006.9

  Reactions of 2-(methoxycarbonyl)phenyllead triacetate with β-oxo lactones and phenols in the presence of pyridine afforded polycyclic lactones in good yields. A one-pot three-step synthesis without isolation of intermediate products was developed.

  在吡啶存在下，2-(甲氧基羰基)苯基三乙酸铅与β-氧代内酯和酚的反应以良好的产率得到多环内酯。开发了不分离中间产物的一锅三步合成法。
• 2-(Azidomethyl)arylboronic Acids in the Synthesis of Coumarin-Type Compounds
  作者：Alexey Fedorov、Mikael Naumov、Alexander Nuchev、Nikolay Sitnikov、Yulia Malysheva、Andrew Shavyrin、Irina Beletskaya、Andrei Gavryushin、Sebastien Combes

  DOI：10.1055/s-0028-1088058

  日期：2009.5

  involvement into organolead-mediated Pinhey arylation reaction with 4-hydroxycoumarins afforded 3-[2-(azidomethyl)aryl]-4-hydroxycoumarins or [4,3-c]isoquinolino­coumarins in reasonable yields via two- or four-step one-pot reaction sequence. Palladium-catalyzed cross-coupling of organoboron reagents with 4-trifluoromethylsulfonyloxycoumarins under Suzuki reaction conditions gave 4-[2-(azidomethyl)aryl]coumarins

  合成了几种2-（叠氮甲基）芳基硼酸。他们通过与4-羟基香豆素一起参与有机铅介导的Pinhey芳基化反应，通过两步或四步一锅法以合理的产率获得了3- [2-（叠氮甲基）芳基] -4-羟基香豆素或[4,3- c ]异喹啉香豆素。反应顺序。在Suzuki反应条件下，钯催化的有机硼试剂与4-三氟甲基磺酰氧基香豆素的交叉偶联以良好的产率得到了4- [2-（叠氮甲基）芳基]香豆素。2-（叠氮基甲基）芳基硼酸以及含叠氮化物的异黄酮和新黄酮类化合物在THF水中进行炔烃-叠氮化物的催化加成反应，可选择性地以极好的收率提供1,4-三唑化合物。 香豆素-叠氮化物-芳基化-交叉偶联-环加成
• 2-(Azidomethyl)phenylboronic acid in the synthesis of isoquinoline derivatives
  作者：O. G. Ganina、S. G. Zamotaeva、M. A. Nosarev、O. V. Kosenkova、M. I. Naumov、A. S. Shavyrin、J.-P. Finet、A. Yu. Fedorov

  DOI：10.1007/s11172-006-0011-y

  日期：2005.7

  Abstract2-(Azidomethyl)phenyllead triacetate was obtained by the reaction of 2-(azidomethyl)phenylboronic acid with lead tetraacetate. A strategy for the synthesis of isoquinoline derivatives was proposed that involves a reaction of this organolead reagent with enolizable substrates followed by annelation in the presence of triphenylphosphine. The use of 2-(azidomethyl)phenylboronic acid allowed α-arylation

  摘要 2-(叠氮甲基)苯基硼酸与四乙酸铅反应制得2-(叠氮甲基)苯基三乙酸铅。提出了一种合成异喹啉衍生物的策略，该策略涉及该有机铅试剂与可烯醇化底物的反应，然后在三苯基膦存在下进行退火。使用 2-（叠氮甲基）苯基硼酸可以从 β-二酮和天然 β-氧代内酯以良好的产率获得 α-芳基化产物。