8-bromo-6-chloroflavone | 901768-78-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 8-bromo-6-chloroflavone
• 英文别名: 8-Bromo-6-chloro-2-phenyl-4H-1-benzopyran-4-one；8-bromo-6-chloro-2-phenylchromen-4-one
• CAS: 901768-78-3
• 化学式: C₁₅H₈BrClO₂
• 分子量: 335.584
• InChiKey: QQPCTTAPOFZBGU-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C
• 沸点：
  460.0±45.0 °C(Predicted)
• 密度：
  1.617±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-bromo-6-chloroflavone 在 palladium diacetate 、 tris(dibenzylideneacetone)dipalladium (0) 三乙胺 、 三(邻甲基苯基)磷 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 6,8-bis(2-methoxycarbonylethenyl)-flavone
  参考文献：
  名称：

  A Scaffold Approach to 3,6,8-Trisubstituted Flavones

  摘要：

  基于钯介导的偶联反应，我们开发出了一种高效的 3,6,8-三取代黄酮支架合成方法。

  DOI：

  10.1055/s-2006-939040
• 作为产物：
  描述：

  1-(3-bromo-5-chloro-2-hydroxyphenyl)-3-phenylpropane-1,3-dione 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 14.0h， 以82%的产率得到8-bromo-6-chloroflavone
  参考文献：
  名称：

  A Scaffold Approach to 3,6,8-Trisubstituted Flavones

  摘要：

  基于钯介导的偶联反应，我们开发出了一种高效的 3,6,8-三取代黄酮支架合成方法。

  DOI：

  10.1055/s-2006-939040

文献信息

• Synthesis of 2,3,6,8-Tetrasubstituted Chromone Scaffolds
  作者：Kristian Dahlén、Erik A. A. Wallén、Morten Grøtli、Kristina Luthman

  DOI：10.1021/jo061008f

  日期：2006.9.1

  A useful and efficient synthetic strategy to 2,3,6,8-tetrasubstituted chromone derivatives has been developed. 2-Aryl/styryl-8-bromo-6-chloro-3-hydroxychromone derivatives were synthesized and used as scaffolds by introducing a variety of substituents in the 3-, 6-, and 8-positions using palladium-mediated reactions. Excellent regioselectivity in all positions could be obtained by performing reactions in the 8-position first, in which Stille, Heck, Suzuki, and Sonogashira reactions gave good to excellent yields of product (63-98%). Stille and Heck reactions in the 6- position also gave the desired products in good yields (64-86%). The hydroxy group in the 3- position was activated as a triflate and used in productive Stille reactions (63-94%). This hydroxyl group was also used in O-alkylation reactions with different functionalized alkyl bromides (57-88%). The flavonoids, which are based on the chromone structure, and other related ring systems, have several interesting biological activities. The chromones are also interesting structural scaffolds, and they have for example been designed to be used as mimetics of short peptides. The versatile applicability of chromone derivatives and especially their potential use in drug discovery implicates the importance of access to efficient synthetic routes to such compounds.
• Synthesis and Evaluation of Substituted Chroman-4-one and Chromone Derivatives as Sirtuin 2-Selective Inhibitors
  作者：Maria Fridén-Saxin、Tina Seifert、Marie Rydén Landergren、Tiina Suuronen、Maija Lahtela-Kakkonen、Elina M. Jarho、Kristina Luthman

  DOI：10.1021/jm3005288

  日期：2012.8.23

  A series of substituted chromone/chroman-4-one derivatives has been synthesized and evaluated as novel inhibitors of SIRT2, an enzyme involved in aging-related diseases, e.g., neurodegenerative disorders. The analogues were efficiently synthesized in a one-step procedure including a base-mediated aldol condensation using microwave irradiation. The most potent compounds, with inhibitory concentrations in the low micromolar range, were substituted in the 2-, 6-, and 8-positions. Larger, electron-withdrawing substituents in the 6- and 8-positions were favorable. The most potent inhibitor of SIRT2 was 6,8-dibromo-2-pentylchroman-4-one with an IC50 of 1.5 mu M. The synthesized compounds show high selectivity toward SIRT2 over SIRT1 and SIRT3 and represent an important starting point for the development of novel SIRT2 inhibitors.
• A Scaffold Approach to 3,6,8-Trisubstituted Flavones
  作者：Kristina Luthman、Kristian Dahlén、Morten Grøtli

  DOI：10.1055/s-2006-939040

  日期：——

  An efficient synthetic approach to 3,6,8-trisubstituted flavone scaffolds has been developed based on Pd-mediated coupling reactions.

  基于钯介导的偶联反应，我们开发出了一种高效的 3,6,8-三取代黄酮支架合成方法。