6-bromo-2'-methoxyflavone | 88952-77-6

• 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: 6-bromo-2'-methoxyflavone
• 英文别名: 6-bromo-2-(2-methoxyphenyl)-4H-chromen-4-one；4H-1-Benzopyran-4-one, 6-bromo-2-(2-methoxyphenyl)-；6-bromo-2-(2-methoxyphenyl)chromen-4-one
• CAS: 88952-77-6
• 化学式: C₁₆H₁₁BrO₃
• 分子量: 331.166
• InChiKey: GLMVAEWDKUOAKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-羟基黄酮 、 6-bromo-2'-methoxyflavone 在 copper(l) iodide 、 N,N-二甲基甘氨酸 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 2-(2-methoxyphenyl)-6-(4-oxo-2-phenyl-4H-chromen-7-yloxy)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of biflavones having a 6-O-7’’ linkage and effects on cyclooxygenase-2 and inducible nitric oxide synthase

  摘要：

  In order to establish anti-inflammatory potential of biflavonoids, 17 biflavone derivatives having a 6-O-7 '' linkage were synthesized and their effects on cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) were evaluated. The basic molecule (6-O-7 '' biflavone) potently inhibited COX-2-mediated PGE(2) production (IC50: < 2 mu M), being less active on iNOS-mediated NO production (IC50: > 50 mu M) from lipopolysaccharide-treated RAW 264.7 cells, a mouse macrophage cell line. Generally, the hydroxyl/methoxyl substitution(s) on the basic biflavone (6-O-7 '') reduced the inhibitory activity of PGE(2) production, while the effects on NO production were varied. It is suggested that the basic biflavone (6-O-7 '') may have a potential for new anti-inflammatory agent. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.017
• 作为产物：
  描述：

  5-溴水杨酸甲酯 在 异丙基氯化镁 、 thallium(III) p-tosylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.17h， 生成 6-bromo-2'-methoxyflavone
  参考文献：
  名称：

  对甲苯磺酸铊催化邻-(Alkynon-1-yl)苯酚区域选择性环化合成黄酮

  摘要：

  DOI：

  10.1002/bkcs.11557

文献信息

• A case study of the iodine‐mediated cyclization of <scp> C ₂ </scp> ′‐ <scp>OH</scp> ‐ and <scp> C ₂ ‐OH </scp> ‐chalcones toward the synthesis of flavones: Reinvestigation of the mechanisms
  作者：Hsin Yen Tsai、Yu‐Tzu Huang、Cing‐Ling Kuo、Chia‐Jou Kuo、Anren Hu、Jih‐Jung Chen、Tzenge‐Lien Shih

  DOI：10.1002/jccs.202000482

  日期：2021.7

  Synthesis of flavones from chalcones via the iodine-mediated cyclization required at least one hydroxy group at their C2′-positions. On the contrary, the ring oxidative cyclization from C2-OH-chalcones under the same condition was unusual and reported only once. We evaluated the aforementioned method and found different results. The mechanisms in detail were discussed.

  通过碘介导的环化从查耳酮合成黄酮需要在其 C 2 '-位至少有一个羟基。相反，C 2 -OH-查耳酮在相同条件下的环氧化环化是不寻常的，仅报道过一次。我们评估了上述方法并发现了不同的结果。详细讨论了这些机制。
• Mazumdar; Karmakar; Tiwari, Journal of the Indian Chemical Society, 1990, vol. 67, # 10, p. 845 - 847
  作者：Mazumdar、Karmakar、Tiwari、Banerjee、Banerji

  DOI：——

  日期：——
• Thakar, K. A.; Gill, C. H., Journal of the Indian Chemical Society, 1983, vol. 60, p. 668 - 670
  作者：Thakar, K. A.、Gill, C. H.

  DOI：——

  日期：——
• THAKAR, K. A.;GILL, C. H., J. INDIAN CHEM. SOC., 1983, 60, N 7, 671-673
  作者：THAKAR, K. A.、GILL, C. H.

  DOI：——

  日期：——
• THAKAR, K. A.;GILL, C. H., J. INDIAN CHEM. SOC., 1983, 60, N 7, 668-670
  作者：THAKAR, K. A.、GILL, C. H.

  DOI：——

  日期：——