8-bromo-6-chloro-3-(ethoxycarbonylmethyloxy)flavone | 910625-88-6

• 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-chloro-3-(ethoxycarbonylmethyloxy)flavone
• 英文别名: Ethyl 2-(8-bromo-6-chloro-4-oxo-2-phenylchromen-3-yl)oxyacetate
• CAS: 910625-88-6
• 化学式: C₁₉H₁₄BrClO₅
• 分子量: 437.674
• InChiKey: CYUOVGNNQOPHCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-bromo-6-chloro-3-(ethoxycarbonylmethyloxy)flavone 、 N-Boc-氨基丙炔 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以83%的产率得到8-[3-(tert-butoxycarbonylamino)-1-propynyl]-6-chloro-3-[ethoxycarbonylmethyloxy]flavone
  参考文献：
  名称：

  Synthesis of 2,3,6,8-Tetrasubstituted Chromone Scaffolds

  摘要：

  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.

  DOI：

  10.1021/jo061008f
• 作为产物：
  描述：

  (E)-1-(3-bromo-5-chloro-2-hydroxyphenyl)-3-phenylprop-2-en-1-one 在 sodium hydroxide 、 双氧水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 8-bromo-6-chloro-3-(ethoxycarbonylmethyloxy)flavone
  参考文献：
  名称：

  Synthesis of 2,3,6,8-Tetrasubstituted Chromone Scaffolds

  摘要：

  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.

  DOI：

  10.1021/jo061008f