(2-氧代-2H-苯并[h]苯并吡喃-4-基)乙酸 | 101999-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 中文名称: (2-氧代-2H-苯并[h]苯并吡喃-4-基)乙酸
• 英文名称: 2(H)-oxonaphtho<1,2-b>pyran-2-acetic acid
• 英文别名: 2(H)-oxonaphtho<1,2-b>pyran-4-acetic acid；2-oxo-2H-naphtho<1,2-b>pyran-4-acetic acid；2-(2-oxo-2H-benzo[h]chromen-4-yl)acetic acid；(2-oxo-2H-benzo[h]chromen-4-yl)acetic acid；(2-Oxo-2H-benzo[h]chromen-4-yl)-essigsaeure；2-(2-oxobenzo[h]chromen-4-yl)acetic acid
• CAS: 101999-46-6
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: VATASCPGAABWET-UHFFFAOYSA-N

物化性质

• 熔点：
  212-213 °C
• 沸点：
  531.7±38.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 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：

  (2-氧代-2H-苯并[h]苯并吡喃-4-基)乙酸 在 硫酸 、 sodium ethanolate 作用下， 以 苯 为溶剂， 反应 15.0h， 生成 2-(2-oxo-2H-naphtho<1,2-b>pyran-4-yl)glutarimide
  参考文献：
  名称：

  El-Nagdy, Sayed; Soliman, Ahmed Youssef; El-Bassiouny, Fakhry Abd-el Aziz, Acta Chimica Hungarica, 1991, vol. 128, # 1, p. 35 - 40

  摘要：

  DOI：
• 作为产物：
  描述：

  萘酚 、 柠檬酸 在 硫酸 作用下， 反应 48.0h， 生成 (2-氧代-2H-苯并[h]苯并吡喃-4-基)乙酸
  参考文献：
  名称：

  Molecular structure, optoelectronic properties, spectroscopic (FT-IR, FT-Raman and UV–Vis), H-BDE, NBO and drug likeness investigations on 7, 8-benzocoumarin-4-acetic acid (7BAA)

  摘要：

  Experimental and theoretical spectroscopic studies were performed for the 7, 8-benzocoumarin-4-acetic acid (7BAA). The research work was performed in two levels. In the first level, experimental FT-IR, FT-Raman and UV-Vis spectral data were recorded. In the next level, the theoretical computations have been conducted from DFT\B3LYP\6-311++G (d, p) basis level. Initially theoretical geometrical parameters were obtained and compared with the related experimental parameters. The computed FT-IR and FT-Raman frequencies collected from same basis level and compared with experimental data. The important wavenumber assignments were achieved on the PED of individual vibrational mode. Theoretical (TD-DFT) and experimental UV-Vis absorption wavelengths (lambda) were compared with each other. The FMO, NBO, MEP analyses were performed. In addition, molecular dynamic (MD) simulations, molecular docking and selected optoelectronic properties have been studied. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.06.032

文献信息

• Facile intramolecular Diels–Alder reaction of 4-(o-propargyloxy)styrylcoumarins leading to highly fluorescent coumarin-containing polycyclic compounds
  作者：Adil I. Khatri、Shriniwas D. Samant

  DOI：10.1016/j.tetlet.2014.02.102

  日期：2014.4

  O-propargylated salicylaldehyde with substituted coumarin-4-acetic acids. The intramolecular Diels–Alder reaction of 4-(o-propargyloxy)styrylcoumarins, without any catalyst gives fused-ring coumarins. The reaction in boiling nitrobenzene leads to aromatization of the initial Diels–Alder adduct and these aromatized products are highly fluorescent.

  4-（邻-炔丙基氧基）苯乙烯基香豆素是通过将邻-炔丙基化的水杨醛与取代的香豆素-4-乙酸缩合而制备的。4-（邻-炔丙基氧基）苯乙烯基香豆素的分子内Diels-Alder反应，无需任何催化剂，即可得到稠环香豆素。沸腾的硝基苯中的反应导致最初的Diels–Alder加合物芳构化，这些芳构化的产品具有很高的荧光性。
• Synthesis of potentially photoactivatable coumarin derivatives<i>via</i>a 1,3-dipolar cycloaddition
  作者：Elodie-Denise Chenot、Juan Carlos Rodríguez-Domínguez、Alain Comel、Gilbert Kirsch、Paul Hannewald

  DOI：10.1002/jhet.5570450528

  日期：2008.9

  (1)-catalyzed 1,3-dipolar cycloaddition reaction was used to prepare a series of mono and disubstituted 1,2,3-triazolyl-coumarins using a 1,3-cycloaddition (“Click Chemistry”). Starting coumarins were synthesized using classical or modified Pechmann's reaction. The propargyl group was introduced as either propargylether or as a propargylamide. Azides were prepared in a three steps procedure. Cycloaddition products

  铜（1）催化的1，3-偶极环加成反应被用于使用1，3-环加成反应制备一系列单和双取代的1,2,3-三唑基-香豆素（“点击化学”）。起始香豆素是使用经典或改良的Pechmann反应合成的。炔丙基作为炔丙基醚或炔丙基酰胺被引入。叠氮化物按三步法制备。以高收率获得了包含香豆素和可光活化部分的环加成产物。
• Synthesis, structure and DNA cleavage studies of coumarin analogues of tetrahydroisoquinoline and protoberberine alkaloids
  作者：Vithal B. Jadhav、Susanta K. Nayak、T.N. Guru Row、M.V. Kulkarni

  DOI：10.1016/j.ejmech.2010.04.041

  日期：2010.9

  Novel molecular matrices have been derived from coumarin-4-acetic acids and β-phenylethylamines using the Bischler–Napieralski protocol which has led to the synthesis of analogues of tetrahydropapaverine in which the dimethoxybenzene moiety has been replaced by substituted coumarins. One carbon homologation has led to cyclization at the C3 position of coumarin generating the protoberberine skeleton

  使用Bischler-Napieralski协议已从香豆素-4-乙酸和β-苯乙胺衍生出新型分子基质，该协议已合成四氢罂粟碱的类似物，其中二甲氧基苯部分已被取代的香豆素取代。一种碳同源性导致香豆素的C3位置环化，生成原小ber碱骨架。通过衍射研究已经确认了结构。结果表明，化合物6e，6f，7e和7f对革兰氏阳性菌金黄色葡萄球菌和黑曲霉的DNA样品十分有效。
• Synthesis and rat lens aldose reductase inhibitory activity of some benzopyran-2-ones
  作者：Abram N. Brubaker、Jack De Ruiter、William L. Whitmer

  DOI：10.1021/jm00156a031

  日期：1986.6

  A number of 4,7-disubstituted benzopyran-2-ones were synthesized and evaluated for crude rat lens aldose reductase inhibitory activity. Substituents on position 4 included CH3, CO2H, CH2CO2H, CH = CHCO2H, and CH2CH2CO2H. The aromatic substituents included OH, OCH3, OCOCH3, CH2CH3, and Cl. Also included in the study were 3-oxo-3H-naphtho[2,1-b]pyran-1-acetic, 2-oxo-2H-naphtho[1,2-b]pyran-4-acetic, and 1-naphthylacetic acids. The benzopyran and naphthopyran derivatives were prepared by the classical von Pechmann reaction. General structure-activity relationships reveal that optimal enzyme inhibitory activity is displayed by those compounds possessing the acetic acid moiety. For example, the most potent derivative, 3-oxo-3H-naphtho[2,1-b]pyran-1-acetic acid with an IC50 of 0.020 microM, is as potent as sorbinil (IC50 = 0.017 microM) in the crude rat lens aldose reductase assay.
• Mashelkar, U. S.; Walavalkar, K. V.; Arvindakshan, C. N., Journal of the Indian Chemical Society, 1992, vol. 69, # 7, p. 404 - 405
  作者：Mashelkar, U. S.、Walavalkar, K. V.、Arvindakshan, C. N.、Singh, Anil

  DOI：——

  日期：——