5-羟基-7-甲氧基香豆素 | 23053-61-4

• 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
• 中文名称: 5-羟基-7-甲氧基香豆素
• 英文名称: 5,7-dihydroxycoumarin 7-methyl ether
• 英文别名: 5-hydroxy-7-methoxycoumarin；isoscopoletin；5-hydroxy-7-methoxy-chromen-2-one；5-hydroxy-7-methoxy-coumarin；5-Hydroxy-7-methoxy-cumarin；5-hydroxy-7-methoxychromen-2-one
• CAS: 23053-61-4
• 化学式: C₁₀H₈O₄
• mdl: MFCD24392728
• 分子量: 192.171
• InChiKey: CPPAWCQANCLZEO-UHFFFAOYSA-N

物化性质

• 熔点：
  228-229 °C
• 沸点：
  409.6±45.0 °C(Predicted)
• 密度：
  1.377

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  5-羟基-7-甲氧基香豆素 在 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Structures of antimutagenic constituents in the peels of Citrus limon

  摘要：

  从柠檬（Citrus limon）果皮提取的甲醇提取物在Ames试验中显示出对3-氨基-1,4-二甲基-5H-吡啶[4,3-b]吲哚和2-氨基-1-甲基-6-苯基咪唑[4,5-b]吡啶（PhIP）的抗突变效应。通过甲醇提取物，分离出了四种新香豆素（wakayamalimonol A–D）和一种新呋喃香豆素（wakayamalimonol E），以及十五种已知化合物。新化合物的绝对立体结构通过化学合成和改进的Mosher法确定。在分离的成分中，香豆素、呋喃香豆素和柠檬素类在Ames试验中显示出抗突变效应。其中一种主要成分，柠檬素，在体内的微核实验中对美克霉素C和PhIP显示了显著的抗突变效应。

  DOI：

  10.1007/s11418-017-1108-3
• 作为产物：
  描述：

  5-香叶氧基-7-甲氧基香豆素 在 硫酸 、 溶剂黄146 作用下， 生成 5-羟基-7-甲氧基香豆素
  参考文献：
  名称：

  Chemical Composition of Lemon Oil. I. Isolation of a Series of Substituted Coumarins¹

  摘要：

  DOI：

  10.1021/ja01570a049

文献信息

• A Catalyst-Free One-Pot Construction of Skeletons of 5-Methoxyseselin and Alloxanthoxyletin in Water
  作者：Jin-Li Cao、Su-Li Shen、Peng Yang、Jin Qu

  DOI：10.1021/ol401581p

  日期：2013.8.2

  In refluxing water and without an additional catalyst, electron-rich phenols could react with alkynoic acids or alkynoates to provide coumarin structures. The skeletons of two natural pyranocoumarins, 5-methoxyseselin and alloxanthoxyletin, could be constructed (total yield up to 76%) in an aqueous multicomponent reaction in which isoprenyl acetate, propiolic acid, and phloroglucinol were simply mixed

  在回流水中且没有其他催化剂的情况下，富含电子的酚可能与炔酸或炔酸反应生成香豆素结构。可以在水性多组分反应中构建两种天然吡喃香豆素的骨架，即5-甲氧基水杨素和别氧蒽氧基letletanthoxyletin（总收率高达76％），其中将异戊二烯乙酸酯，丙酸和间苯三酚简单地混合并在水中回流。
• Studies on coumarins from the root of Angelica pubescens Maxim. III. Structures of various coumarins including angelin, a new prenylcoumarin.
  作者：MITSUGI KOZAWA、KIMIYE BABA、YOUKO MATSUYAMA、KIYOSHI HATA

  DOI：10.1248/cpb.28.1782

  日期：——

  Two prenylcoumarins, XII and XIII, were isolated from the root of Angelica pubescens MAXIM. (Umbelliferae) growing in Japan, together with eleven known coumarins, osthol (I), bergapten (II), glabra-lactone (III), angelol (IV), psoralen (V), xanthotoxin (VI), isopimpinellin (VII), byak-angelicin (VIII), coumurrayin (IX), 7-methoxy-8-senecioylcoumarin (X) and scopoletin (XI). The structures of XII and XIII were elucidated as 8-(3-hydroxyisovaleroyl)-5, 7-dimethoxycoumarin and 5-isopentenyloxy-7-methoxy-8-senecioylcoumarin, respectively, by chemical and spectral studies. XIII is a new natural prenylcoumarin, and was named angelin.

  从生长在日本的当归（伞形科）的根中分离出两种异戊烯基香豆素，即XII和XIII，以及11种已知的香豆素，即osthol（I）、bergapten（II）、glabra-lactone（III）、angelol（IV）、psoralen（V）、xanthotoxin（VI）、isopimpinellin（VII）、byak-angelicin（VIII）、coumurrayin（IX）、7-methoxy-8-senecioylcoumarin（X）和scopoletin（XI）。通过化学和光谱研究，XII和XIII的结构分别被阐明为8-(3-羟基异戊酰基)-5,7-二甲氧基香豆素和5-异戊烯氧基-7-甲氧基-8-千里光基香豆素。XIII是一种新的天然异戊烯基香豆素，被命名为angelin。
• Atom Economy. Palladium-Catalyzed Formation of Coumarins by Addition of Phenols and Alkynoates via a Net C−H Insertion
  作者：Barry M. Trost、F. Dean Toste、Kevin Greenman

  DOI：10.1021/ja0286573

  日期：2003.4.1

  A strategy to achieve ortho substitution of phenols initiated by an ortho-palladation to create coumarins was examined. Indeed, treatment of alkynoates with electron-rich phenols in the presence of a palladium catalyst and an acid does generate coumarins. The scope of the reaction with respect to the phenol and the alkynoates is defined. With unsymmetrical aromatic substrates, generally good regioselectivity that reflects the HOMO coefficients can be observed. In the course of these studies, numerous important naturally occurring coumarins have been synthesized, including fraxinol methyl ether, ayapin, herniarin, xanthoxyletin, and alloxanthoxyletin. The fact that a Pd(0) is the precatalyst rather than a Pd(+2) species and that an acid that reduces Pd(+2) salts, formic acid, functions better than other carboxylic acids raises doubts about the initial working hypothesis. A novel mechanism involving a palladium phenoxide formed from a hydridopalladium carboxylate and phenol is invoked to rationalize the results.
• Natural oxyprenylated coumarins are modulators of melanogenesis
  作者：Serena Fiorito、Francesco Epifano、Francesca Preziuso、Ivana Cacciatore、Antonio di Stefano、Vito Alessandro Taddeo、Philippe de Medina、Salvatore Genovese

  DOI：10.1016/j.ejmech.2018.04.051

  日期：2018.5

  Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor 13 and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect. The parent compound with a free OH group, umbelliferone, did not provide any interaction. Other coumarins assayed, having shorter chains and/or being substituted in other positions, and prenyloxypsoralens, were not active or not further investigated in this context being cytotoxic at low doses. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Natural product chemistry. Part 121. Synthesis of dicoumarinyl ethers with the structures proposed for fatagarine and oreojasmine
  作者：Johannes Reisch、Anura Wickramasinghe、Vijaya Kumar

  DOI：10.1007/bf00808314

  日期：1988.11