7-hydroxy-8-propionyl-coumarin | 67752-18-5

• 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
• 英文名称: 7-hydroxy-8-propionyl-coumarin
• 英文别名: 7-Hydroxy-8-propionyl-cumarin；7-hydroxy-8-propanoylchromen-2-one
• CAS: 67752-18-5
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: DVLIOVBNBOBBGS-UHFFFAOYSA-N

物化性质

• 熔点：
  168 °C(Solv: ethanol (64-17-5))
• 沸点：
  431.2±45.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  7-hydroxy-8-propionyl-coumarin 生成 7-ethoxy-8-propionyl-coumarin
  参考文献：
  名称：

  Shah; Contractor, Journal of the Indian Chemical Society, 1959, vol. 36, p. 679

  摘要：

  DOI：
• 作为产物：
  描述：

  7-(propanoyl)oxy-2H-1-benzopyran-2-one 在 三氯化铝 作用下， 生成 7-hydroxy-8-propionyl-coumarin
  参考文献：
  名称：

  Shah; Contractor, Journal of the Indian Chemical Society, 1959, vol. 36, p. 679

  摘要：

  DOI：

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。
• 7,8-Disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range
  作者：Alfonso Maresca、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2010.10.094

  日期：2010.12

  Two series of disubstituted coumarins incorporating ether and acetyl/propionyl moieties in positions 6,7- and 7,8- of the heterocyclic ring were synthesized investigated for the inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). All these coumarins were very weak or ineffective as inhibitors of the housekeeping, offtarget isoforms CA I and II. The 6,7-disubstituted series showed ineffective inhibition also for the transmembrane tumor-associated isoforms CA IX and XII, whereas the corresponding isomeric 7,8-disubstituted coumarins showed nanomolar/subnanomolar inhibition of CA IX/XII. The nature and position of the groups substituting the coumarin ring in the 7,8-positions greatly influenced CA inhibitory properties, with C1-C4 alkyl ethers being the most effective inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.
• Shah; Contractor, Journal of the Indian Chemical Society, 1959, vol. 36, p. 679
  作者：Shah、Contractor

  DOI：——

  日期：——