8-Benzoyl-7-hydroxy-4-methylcoumarin | 20312-83-8

• 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-hydroxy-4-methylcoumarin
• 英文别名: 8-benzoyl-7-hydroxy-4-methyl-coumarin；8-Benzoyl-7-hydroxy-4-methyl-cumarin；8-benzoyl-7-hydroxy-4-methyl-chromen-2-one；8-Benzoyl-7-hydroxy-4-methyl-2H-chromen-2-one；8-benzoyl-7-hydroxy-4-methylchromen-2-one
• CAS: 20312-83-8
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: RKARRKKWKBCKLN-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C
• 沸点：
  513.5±50.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-hydroxy-4-methylcoumarin 在 sodium hydroxide 作用下， 生成 (2,6-dimethoxyphenyl)(phenyl)methanone
  参考文献：
  名称：

  Limaye, Chemische Berichte, 1934, vol. 67, p. 12,14

  摘要：

  DOI：
• 作为产物：
  描述：

  4-methyl-2-oxo-2H-chromen-7-yl benzoate 在 三氯化铝 作用下， 生成 8-Benzoyl-7-hydroxy-4-methylcoumarin
  参考文献：
  名称：

  Limaye, Chemische Berichte, 1934, vol. 67, p. 12,14

  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）。
• An Efficient, Mild and Scalable Synthesis of Bioactive Compounds Containing the Angelicin Scaffold
  作者：Shiao Hui-Yi、Kuo Ching-Chuan、Horng Jim-Tong、Shih Shin-Ru、Chang Sui-Yuan、Liao Chun-Chen、Hsu John T.-A.、Amancha Prashanth Kumar、Chao Yu-Sheng、Hsieh Hsing-Pang

  DOI：10.1002/jccs.201200233

  日期：2012.12

  An efficient, mild and scalable synthesis of angelicin scaffold based compounds was developed. Particularly, the new synthetic route described here circumvents the need for the previously reported key Fries rearrangement step, which uses impractically harsh conditions. The new methodology is applied to the synthesis of several, previously reported analogs of angelicin which have potent anti‐influenza

  开发了一种高效，温和且可扩展的基于安吉林支架的化合物合成方法。特别地，此处描述的新合成路线避免了先前报告的关键Fries重排步骤的需要，该步骤使用了不切实际的苛刻条件。新的方法学被用于合成许多先前报道的具有强力抗流感和抗癌活性的当归霉素类似物。
• COUMARIN COMPOUNDS AND THEIR USE FOR TREATING VIRAL INFECTION
  申请人：Hsieh Hsing-Pang

  公开号：US20090312406A1

  公开（公告）日：2009-12-17

  A method for treating an infection with a virus. The method includes administering to a subject in need thereof an effective amount of one or more coumarin compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and X are defined herein. Also disclosed is a pharmaceutical composition including a coumarin compound.

  一种治疗病毒感染的方法。该方法包括向需要的受试者施用一种或多种符合以下化学式（I）的香豆素化合物的有效量：其中R1、R2、R3、R4、R5、R6和X在此定义。还公开了包括香豆素化合物的药物组合物。
• COUMARIN COMPOUNDS AND THEIR USE FOR TREATING CANCER
  申请人：Hsieh Hsing-Pang

  公开号：US20090312317A1

  公开（公告）日：2009-12-17

  Coumarin compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and X are defined herein. Also disclosed is a method for treating cancer with coumarin compounds.

  公式（I）的香豆素化合物：其中R1、R2、R3、R4、R5、R6和X在此定义。还公开了一种使用香豆素化合物治疗癌症的方法。
• 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。