8-Benzoyl-7-hydroxycoumarin | 90104-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8-Benzoyl-7-hydroxycoumarin
• 英文别名: 8-benzoyl-7-hydroxy-coumarin；8-Benzoyl-7-hydroxy-cumarin；8-Benzoyl-7-hydroxychromen-2-one
• CAS: 90104-85-1
• 化学式: C₁₆H₁₀O₄
• 分子量: 266.253
• InChiKey: JNLMTHJRVMCHKO-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C(Solv: acetic acid, 30% (64-19-7))
• 沸点：
  513.7±50.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-Benzoyl-7-hydroxycoumarin 在 alkaline solution 、 potassium carbonate 、 丙酮 作用下， 生成 (8-benzoyl-2-oxo-2H-chromen-7-yloxy)-acetic acid
  参考文献：
  名称：

  FURANOCOUMARINS AND COUMARINO-α- AND γ-PYRONES

  摘要：

  DOI：

  10.1021/jo01377a010
• 作为产物：
  描述：

  7-Benzoyloxycoumarin 在 三氯化铝 作用下， 生成 8-Benzoyl-7-hydroxycoumarin
  参考文献：
  名称：

  THE FRIES ISOMERIZATION OF ACETYL AND BENZOYL ESTERS OF UMBELLIFERONES

  摘要：

  DOI：

  10.1021/jo01375a018

文献信息

• One-pot synthesis of angular furocoumarins: A simple protocol involving unprecedented intramolecular aldol condensation
  作者：Lakshmi Narayan Dutta、Banani De、Amarendra Patra

  DOI：10.1002/jhet.5570450306

  日期：2008.5

  Refluxing of hydroxycoumarinyl ketones with methyl γ-bromocrotonate in dry acetone in presence of anhydrous K2CO3 afforded substituted angelicins (angular furanocoumarins) in satisfactory yields through intramolecular Aldol condensation followed by β-elimination.

  在无水K 2 CO 3的存在下，在干燥的丙酮中将γ-溴代巴豆酸甲酯与羟基香豆素基酮回流，通过分子内Aldol缩合，然后进行β消除，以令人满意的产率提供了取代的当归类（角呋喃香豆素）。
• Feasibility of sigmatropic rearrangement on electron-deficient coumarinyl ketones
  作者：Lakshmi Narayan Dutta、Banani De、Godhuli Pal、Amarendra Patra

  DOI：10.1139/v08-037

  日期：2008.5.1

  Different alkyl/aryl 7-hydroxy-8-coumarinyl ketones were converted to 7-O-allyl and 7-O-cyclohexenyl ethers and the study of hitherto unreported sigmatropic rearrangement on 7-O-allyl and 7-O-cyclohex-2'-ene-1'-ylcoumarinyl ketones prepared is accounted herein. The rearrangement yielded alkyl/aryl 6-allyl-7-hydroxy-8-coumarinyl ketones 3 and alkyl/aryl 6-cyclohex-2'-en-1'-yl-7-hydroxy-8-coumarinyl ketones 7 as the major products. Interestingly, unusual selectivity was observed in the case of alkyl 7-O-allylcoumarinyl ketones. Thus alkyl 3-allyl-7-hydroxy-8-coumarinyl ketones 4 and alkyl 8-allyl-7-hydroxy-6-coumarinyl ketones 5 were the outcome from alkyl 7-O-allyl-8-coumarinyl ketones and alkyl 4-methyl-7-O-allyl-8-coumarinyl ketones, respectively, albeit in minor yields.Key words: allyloxycoumarinyl ketones, 7-O-cyclohex-2'-en-1'-ylcoumarinyl ketones, sigmatropic rearrangement, 3-allylcoumarinyl ketones, 8-allylcoumarinyl ketones.

  不同的烷基/芳基 7-羟基-8-香豆素酮被转化为 7-O-烯丙基醚和 7-O-环己烯基醚，本文介绍了对所制备的 7-O-烯丙基和 7-O-环己烯-2'-烯-1'-基香豆素酮进行的迄今未报道的对称重排的研究。重排的主要产物是烷基/芳基 6-烯丙基-7-羟基-8-香豆素酮 3 和烷基/芳基 6-环己-2'-烯-1'-基-7-羟基-8-香豆素酮 7。有趣的是，在烷基 7-O-烯丙基香豆素酮中观察到了不同寻常的选择性。因此，3-烯丙基-7-羟基-8-香豆素酮烷基 4 和 8-烯丙基-7-羟基-6-香豆素酮烷基 5 分别是 7-O-烯丙基-8-香豆素酮烷基和 4-甲基-7-O-烯丙基-8-香豆素酮烷基的产物，尽管产率较低。关键词：烯丙基香豆素酮、7-O-环己-2'-烯-1'-基香豆素酮、对称重排、3-烯丙基香豆素酮、8-烯丙基香豆素酮。
• ——
  作者：A. Yu. Tolmachev、N. Ya. Podkhalyuzina、N. A. Kuznetsova、V. F. Traven'

  DOI：10.1023/a:1012434702051

  日期：——

  A new procedure was developed for the synthesis of 8-alkoxycarbonylangelieins by base-catalyzed cyclization of ortho-acyl(hydroxy)coumarins with haloacetic acid esters. The procedure was successfully applied to prepare a series of new 8-alkoxycarbonyl- and 8-acylangelicins.
• Kravchenko; Chibisova; Traven', Russian Journal of Organic Chemistry, 1999, vol. 35, # 6, p. 899 - 909
  作者：Kravchenko、Chibisova、Traven'

  DOI：——

  日期：——
• Anti-Influenza Drug Discovery: Structure−Activity Relationship and Mechanistic Insight into Novel Angelicin Derivatives
  作者：Jiann-Yih Yeh、Mohane Selvaraj Coumar、Jim-Tong Horng、Hui-Yi Shiao、Fu-Ming Kuo、Hui-Ling Lee、In-Chun Chen、Chun-Wei Chang、Wen-Fang Tang、Sung-Nain Tseng、Chi-Jene Chen、Shin-Ru Shih、John T.-A. Hsu、Chun-Chen Liao、Yu-Sheng Chao、Hsing-Pang Hsieh

  DOI：10.1021/jm901570x

  日期：2010.2.25

  By using a cell-based high throughput screening campaign,a novel angelicin derivative 6a was identified to inhibit influenza A (H1N1) virus induced Cytopathic effect in Madin-Darby canine kidney cell culture in low micromolar range. Detailed structure-activity relationship studies of 6a revealed that the angelicin scaffold is essential for activity in pharmacophore B, while meta-substituted phenyl/2-thiophene rings are optimal ill pharmacophore A and C. The optimized lead 4-methyl-9-phenyl-8-(thiophene-2-carbonyl)-furo[2,3-h]chromen-2-one (8g, IC50 = 70 nM) showed 64-fold enhanced activity compared to the high throughput screening (HTS) hit 6a. Also, 8g was found effective in case of influenza A (H3N2) and influenza B virus strains similar to approved anti-influenza drug zanamivir (4). Preliminary mechanistic studies suggest that these compounds act as anti-influenza agents by inhibiting ribonucleoprotein (RNP) complex associated activity and have the potential to be developed further, Which Could form the basis for developing additional defense against influenza pandemics.