7-羟基-5-甲氧基-4-甲基-2H-1-苯并吡喃-2-酮 | 6093-81-8

• 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: 7-羟基-5-甲氧基-4-甲基-2H-1-苯并吡喃-2-酮
• 英文名称: 7-hydroxy-5-methoxy-4-methylcoumarin
• 英文别名: 7-hydroxy-5-methoxy-4-methylchromen-2-one
• CAS: 6093-81-8
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: OJLATCGOJCUTJG-UHFFFAOYSA-N

物化性质

• 熔点：
  252-253 °C
• 沸点：
  425.9±45.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

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：

  7-羟基-5-甲氧基-4-甲基-2H-1-苯并吡喃-2-酮 在 sodium hydroxide 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 51.0h， 生成 6,7,8,9-tetrahydro-5-methoxy-4-methylbenzofuro[3,2-g]coumarin
  参考文献：
  名称：

  Synthesis of Linear and Angular Benzofurocoumarins

  摘要：

  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。

  DOI：

  10.1055/s-1997-1381
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 7-羟基-5-甲氧基-4-甲基-2H-1-苯并吡喃-2-酮
  参考文献：
  名称：

  Desai; Parghi, Journal of the Indian Chemical Society, 1956, vol. 33, p. 661,663

  摘要：

  DOI：

文献信息

• Anti-AIDS Agents. 42. Synthesis and Anti-HIV Activity of Disubstituted (3‘<i>R</i>,4‘<i>R</i>)-3‘,4‘-Di-<i>O</i>-(<i>S</i>)-camphanoyl-(+)-<i>cis</i>-khellactone Analogues
  作者：Lan Xie、Yasuo Takeuchi、L. Mark Cosentino、Andrew T. McPhail、Kuo-Hsiung Lee

  DOI：10.1021/jm000070g

  日期：2001.3.1

  series of disubstituted 3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) analogues (1-10) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. 5-Methoxy-4-methyl DCK (8) was the most promising compound with an EC(50) value of 7.21 x 10(-6) microM and a therapeutic index of >2.08 x 10,(7) which were much better than those of lead compound DCK in the same assay. Another

  合成了一系列双取代的3'，4'-di-O-（S）-樟脑酰基-（+）-顺式-甲壳酮（DCK）类似物（1-10），并评估了其对H9淋巴细胞中HIV-1复制的抑制作用。5-甲氧基-4-甲基DCK（8）是最有前途的化合物，EC（50）值为7.21 x 10（-6）microM，治疗指数> 2.08 x 10，（7）比同一试验中铅化合物DCK的那些。另外六个双取代的DCK类似物（1-5和7）比AZT更有效，但比DCK活性低。构象分析表明，香豆素系统的共振是有效的抗HIV活性的基本结构特征。香豆素部分的C（4）和C（5）取代基的立体压缩可以降低总体平面度，从而减少香豆素核的共振，从而导致抗HIV活性降低或缺乏。
• Furocoumarin for the photochemotherapy of psoriasis and related skin
  申请人：Consiglio Nazionale delle Ricerche

  公开号：US04312883A1

  公开（公告）日：1982-01-26

  A class of alkyl-substituted angular flurocoumarins, sometimes termed alkylangelicins, useful in the photochemotherapy of psoriasis and in other skin diseases characterized by cellular hyperproliferation or lack of skin pigmentation is disclosed for topical application or systemic administration. Compared with conventional psoralens the described compounds exhibit a lower risk of skin cancer, absence of phototoxicity problems anderithema to the patient so treated. One preferred compound is 5-methylangelicin.

  一类烷基取代的角式氟香豆素，有时被称为烷基安琪素，可用于治疗银屑病等细胞过度增生或皮肤色素缺乏的其他皮肤疾病的光化疗，适用于局部应用或全身给药。与传统的毒芹素相比，所述化合物表现出较低的皮肤癌风险，对接受治疗的患者没有光毒性问题和红斑痤疮。一个优选的化合物是5-甲基安琪素。
• Synthesis and complete assignment of the1H and13C NMR signals of some oxopyrancoumarin and oxofuropyrancoumarin derivatives
  作者：Elías Quezada、Giovanna Delogu、Dolores Viña、Lourdes Santana、Carmen Picciau、Gianni Podda、Eugenio Uriarte

  DOI：10.1002/mrc.2223

  日期：2008.7

  The synthesis of four pyranocoumarins starting from phloroglucinol and the complete 1H and 13C NMR assignment of seven pyranocoumarins has been performed using 1D and 2D NMR techniques including COSY, HMQC and HMBC experiments. Copyright © 2008 John Wiley & Sons, Ltd.

  从间苯三酚开始合成四种吡喃香豆素，并使用 1D 和 2D NMR 技术（包括 COSY、HMQC 和 HMBC 实验）对七种吡喃香豆素进行了完整的 1H 和 13C NMR 分配。版权所有 © 2008 John Wiley & Sons, Ltd.
• 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.