8-butyryl-7-hydroxy-4-methyl-coumarin | 90104-80-6

• 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: 8-butyryl-7-hydroxy-4-methyl-coumarin
• 英文别名: 8-Butyryl-7-hydroxy-4-methyl-cumarin；8-Butanoyl-7-hydroxy-4-methylchromen-2-one
• CAS: 90104-80-6
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: BABIEVPCZBSYOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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-butyryl-7-hydroxy-4-methyl-coumarin 在 sodium hydroxide 作用下， 生成 1-(2,6-二羟基苯基)丁烷-1-酮
  参考文献：
  名称：

  Limaye; Talwalkar, Rasayanam, 1938, vol. 1, p. 141,143

  摘要：

  DOI：
• 作为产物：
  描述：

  羟甲香豆素 在 三氯化铝 作用下， 生成 8-butyryl-7-hydroxy-4-methyl-coumarin
  参考文献：
  名称：

  Limaye; Talwalkar, Rasayanam, 1938, vol. 1, p. 141,143

  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。
• 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.
• Schamschurin; Archangelskaja, Nr. 25 Chimija Nr. 1<1941>9, 14
  作者：Schamschurin、Archangelskaja

  DOI：——

  日期：——