5-羟基-7-甲氧基-4-甲基-2H-1-苯并吡喃-2-酮 | 6795-19-3

• 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-4-甲基-2H-1-苯并吡喃-2-酮
• 英文名称: 5-hydroxy-7-methoxy-4-methylcoumarin
• 英文别名: 5-Hydroxy-7-methoxy-4-methylchromen-2-one
• CAS: 6795-19-3
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: ISPQCFBFSGLMOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-羟基-7-甲氧基-4-甲基-2H-1-苯并吡喃-2-酮 在 selenium(IV) oxide 、 zinc(II) chloride 、 锌 、 三氯氧磷 作用下， 以 乙醇 、 水 、 溶剂黄146 、 xylene 为溶剂， 反应 46.0h， 生成 3,3'-(phenylmethylene)bis(4-hydroxy-5-methoxy-10,10a-dihydro-2H-furo[3',2':4,5]furo[2,3-h]chromene-2,9(7aH)-dione)
  参考文献：
  名称：

  Aflatoxin analogues as possible anticoagulants—I

  摘要：

  DOI：

  10.1016/s0040-4020(01)91953-2
• 作为产物：
  描述：

  夫拉美诺 、 乙酰乙酸乙酯 在 MnSb₂O₆-chitosan nanocomposite 作用下， 以 neat (no solvent) 为溶剂， 反应 0.92h， 以85%的产率得到5-羟基-7-甲氧基-4-甲基-2H-1-苯并吡喃-2-酮
  参考文献：
  名称：

  MnSb2O6-壳聚糖纳米复合材料：通过Pechmann反应合成香豆素的有效催化剂

  摘要：

  在这项工作中，合成了MnSb 2 O 6-壳聚糖纳米复合材料，并已用于Pechmann缩合反应中合成香豆素衍生物。MnSb 2 O 6壳聚糖纳米复合材料的特征在于傅立叶变换红外（FTIR），X射线粉末衍射（XRD），扫描电子显微镜（SEM）和能量分散X射线光谱（EDX）技术。MnSb 2 O 6的颗粒壳聚糖具有尺寸小于100 nm的均匀球体。该反应的优点是简单，易于操作，反应时间短。此外，我们评估了某些产品的抗菌活性，结果显示了作为针对金黄色葡萄球菌和大肠杆菌的抗菌剂的显着药物活性。

  DOI：

  10.1002/jhet.3763

文献信息

• Poly(4-vinylpyridine)-supported sulfuric acid: an efficient solid acid catalyst for the synthesis of coumarin derivatives under solvent-free conditions
  作者：Kalyan Jyoti Borah、Ruli Borah

  DOI：10.1007/s00706-011-0559-6

  日期：2011.12

  AbstractPoly(4-vinylpyridine)-supported sulfuric acid is an efficient catalyst for the Pechmann condensation of acetoacetic esters with phenols, leading to the formation of coumarins in good yields within a few minutes under solvent-free microwave conditions. The catalyst used can be recovered and reused after activation. Graphical abstract

  摘要聚（4-乙烯基吡啶）负载的硫酸是乙酰乙酸酯与苯酚的Pechmann缩合反应的有效催化剂，在无溶剂微波条件下，几分钟内即可形成高产率的香豆素。所用的催化剂可以活化后回收和再利用。 图形概要
• Synthesis of Linear and Angular Benzofurocoumarins
  作者：Carmen Terán、Rocio Miranda、Lourdes Santana、Marta Teijeira、Eugenio Uriarte

  DOI：10.1055/s-1997-1381

  日期：1997.12

  A four-step synthetic approach to substituted linear and angular benzofurocoumarins is described. Starting from 5-methoxyresorcinol, this approach afforded good yields of benzopsoralen (7), benzoangelicine (8), and benzoallopsoralen (11), which bear easily hydrolysed methoxy groups and thus allow access to other substituted compounds with potential as photochemotherapeutic agents.

  描述了取代的线性和有角苯并呋喃香豆素的四步合成方法。从 5-甲氧基间苯二酚开始，这种方法获得了苯并补骨脂素 (7)、苯并当归素 (8) 和苯并别补骨脂素 (11) 的良好产率，它们带有容易水解的甲氧基，因此可以得到其他有潜力作为光化疗剂的取代化合物。
• 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.
• A QSAR Model for in Silico Screening of MAO-A Inhibitors. Prediction, Synthesis, and Biological Assay of Novel Coumarins
  作者：Lourdes Santana、Eugenio Uriarte、Humberto González-Díaz、Giuseppe Zagotto、Ramón Soto-Otero、Estefanía Méndez-Álvarez

  DOI：10.1021/jm0509849

  日期：2006.2.1

  This work explores the potential of the MARCH-INSIDE methodology to seek a QSAR for MAO-A inhibitors from a heterogeneous series of compounds. A Markov model was used to quickly calculate the molecular electron delocalization, polarizability, refractivity, and n-octanol/water partition coefficients for a series of 1406 active/nonactive compounds. LDA was subsequently used to fit a classification function. The model showed 92.8% and 91.8% global accuracy and predictability in training and validation studies. This QSAR model was validated through a virtual screening of a series of cournarin derivatives. The 15 selected compounds were prepared and evaluated as in vitro MAO-A inhibitors. The theoretical prediction was' compared with the experimental results and the model correctly predicted 13 compounds with only two mistakes on compounds with activities very close to the cutoff point established for the model. Consequently, this method represents a useful tool for the "in silico" screening of MAO-A inhibitors.
• Ultrasound-assisted one-pot synthesis of substituted coumarins catalyzed by poly(4-vinylpyridinium) hydrogen sulfate as an efficient and reusable solid acid catalyst
  作者：Nader Ghaffari Khaligh

  DOI：10.1016/j.ultsonch.2013.01.001

  日期：2013.7

  Poly(4-vinylpyridinium) hydrogen sulfate solid acid was found to be efficient catalyst for synthesis of substituted coumarins via Pechmann reaction using ultrasound irradiation at room temperature and neat condition in high yields with short reaction times. This methodology offers momentous improvements over various options for the synthesis of coumarins with regard to yield of products, simplicity in operation and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be reused and recovered for several times. (C) 2013 Elsevier B.V. All rights reserved.