6,8-二溴黄酮 | 42079-81-2

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 6,8-二溴黄酮
• 英文名称: 6,8-dibromo-2-phenyl-4H-chromen-4-one
• 英文别名: 6,8-dibromoflavone；6,8-dibromo-2-phenyl-chromen-4-one；6,8-Dibrom-2-phenyl-chromen-4-on；6,8-dibromo-2-phenylchromen-4-one
• CAS: 42079-81-2
• 化学式: C₁₅H₈Br₂O₂
• 分子量: 380.035
• InChiKey: OTCPQWYHYLBCIW-UHFFFAOYSA-N

物化性质

• 熔点：
  169-175°C

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  6,8-二溴黄酮 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 50.0h， 生成 6-(4-chlorophenyl)-8-(4-trifluoromethylphenyl)flavone
  参考文献：
  名称：

  Site-Selective Suzuki–Miyaura Reaction of 6,8-Dibromoflavone

  摘要：

  8-Aryl- and 6,8-diarylflavones were prepared by Suzuki-Miyaura reactions of 6,8-dibromoflavone. In spite of the greater steric hindrance, the first attack proceeded with good site selectivity at position 8.

  DOI：

  10.1055/s-0035-1560633
• 作为产物：
  描述：

  3',5'-二溴-2'-羟基苯乙酮 在 吡啶 、 盐酸 、 溶剂黄146 作用下， 反应 20.0h， 生成 6,8-二溴黄酮
  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

文献信息

• Radical-Induced Cascade Annulation/Hydrocarbonylation for Construction of 2-Aryl-4H-chromen-4-ones
  作者：Xinwei He、Keke Xu、Yanan Liu、Demao Wang、Qiang Tang、Wenjie Hui、Haoyu Chen、Yongjia Shang

  DOI：10.3390/molecules27217412

  日期：——

  cleavage/intramolecular 6-endo-dig annulation/hydrocarbonylation for the synthesis of the valuable 2-aryl-4H-chromen-4-ones is described. This practical synthesis strategy utilizes propargylamines and air as the oxygen source and green carbonylation reagent, in which propargylamines are activated by the inexpensive and available dimethyl 2,2′-azobis(2-methylpropionate) (AIBME) and (PhSe)2 as the radical initiators

  描述了一种强大的无金属和无溶剂级联自由基诱导的 CN 裂解/分子内 6-内环化/烃基化，用于合成有价值的 2-芳基-4 H-苯并吡喃-4-酮。这种实用的合成策略利用炔丙胺和空气作为氧源和绿色羰基化试剂，其中炔丙胺被廉价且可用的二甲基2,2'-偶氮二（2-甲基丙酸酯）（AIBME）和（PhSe） 2作为自由基活化发起者。这种简单且绿色的方案具有广泛的底物适应性、良好的官能团耐受性以及易于放大和衍生化的特点。
• Tire with rubber containing flavone
  申请人：THE GOODYEAR TIRE & RUBBER COMPANY

  公开号：EP1391327A1

  公开（公告）日：2004-02-25

  The invention relates to a rubber composition and a pneumatic tire having a component comprising a rubber containing the reaction product of a flavone and a methylene donor.

  本发明涉及一种橡胶组合物和充气轮胎，其成分包括含有黄酮和亚甲基供体反应产物的橡胶。
• Rubber composition and tire with rubber containing flavone
  申请人：The Goodyear Tire & Rubber Company

  公开号：EP2730431A1

  公开（公告）日：2014-05-14

  A rubber composition comprising a diene based elastomer and an adhesion promoter derived from a flavone, a methylene donor and a methylene acceptor is disclosed. The rubber composition is essentially free of cobalt. Also, a pneumatic tire comprising such a rubber composition is disclosed.

  本发明公开了一种橡胶组合物，该组合物包含一种二烯基弹性体和一种由黄酮、亚甲基供体和亚甲基受体衍生的附着力促进剂。该橡胶组合物基本上不含钴。此外，还公开了一种包含这种橡胶组合物的充气轮胎。
• Methods For Treating Wounds
  申请人：Kimberly-Clark Worldwide, Inc.

  公开号：US20030125264A1

  公开（公告）日：2003-07-03

  Pharmaceutical compositions, and methods of using the same, are provided utilizing effective amounts of one or more flavones, flavonols, flavanones, isoflavanones and isoflavones to increase cell proliferation in various tissues and cell lines. As examples, the composition and methods of the present invention can be used to increase proliferation of fibroblast cells and, more particularly, in the treatment of wounds as well as strengthening of the skin.

  本发明提供了利用有效量的一种或多种黄酮、黄酮醇、黄烷酮、异黄烷酮和异黄酮来增加各种组织和细胞系的细胞增殖的药物组合物及其使用方法。举例来说，本发明的组合物和方法可用于增加成纤维细胞的增殖，特别是用于治疗伤口和强化皮肤。
• Ferrocenyl flavonoid-induced morphological modifications of endothelial cells and cytotoxicity against B16 murine melanoma cells
  作者：Jean-Philippe Monserrat、Keshri Nath Tiwari、Lionel Quentin、Pascal Pigeon、Gérard Jaouen、Anne Vessières、Guy G. Chabot、Elizabeth A. Hillard

  DOI：10.1016/j.jorganchem.2012.12.031

  日期：2013.6

  With the aim of improving the cytotoxic and vascular disrupting activities of flavonoids, several classes of ferrocenyl-modified flavonoids were prepared and tested on cancer and endothelial cells. Three tenmember series of ferrocenyl flavonoids: chalcones ((E)-1-(R-2'-hydroxypheny1)-3-ferrocenylprop-2-en-1-ones), aurones ((Z)-R-2-(ferrocenylidene)benzofuran-3-ones) and flavones (R-2-ferrocenyl-chromen-4-ones) were synthesized by recently reported methods. Three ferrocenyl flavonols (R-3-hydroxy2-ferrocenyl-chromen-4-ones) and four ferrocenyl flavanones (3-ferrocenylmethylidenyl-R-2-phenyl-chroman-4-ones) were also obtained. All compounds were evaluated for their cytotoxic effects on a cancer cell line (B16 murine melanoma) and for their morphological effects on endothelial cells (EAhy 926). Some interesting structure-activity relationships were disclosed: of all the compounds, the halogen-substituted aurones showed the best cytotoxic activity, with IC50 values ranging between 12 and 18 mu M. Ferrocenyl flavonols and ferrocenyl flavanones with substitution in the 3-position (-OH and =C-Fc respectively) were not active against cancer or endothelial cells. Some of the ferrocenyl flavones caused the endothelial cells to adopt a round shape ("rounding up") at submicromolar concentrations, which can be predictive of vascular disrupting activity. The most morphologically active flavones showed only moderate cytotoxicity against cancer cells, indicating that they may primarily act as antivascular agents. (C) 2013 Elsevier B.V. All rights reserved.