6,8-dichloro-3-phenylcoumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 6,8-dichloro-3-phenylcoumarin
• 英文别名: 6,8-Dichlor-3-phenyl-cumarin；6,8-Dichloro-3-phenylchromen-2-one；6,8-dichloro-3-phenylchromen-2-one
• 化学式: C₁₅H₈Cl₂O₂
• 分子量: 291.133
• InChiKey: OQXJXKFHJWMSHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：

  6,8-dichloro-3-phenylcoumarin 在 1,10-菲罗啉 、 copper(l) chloride 、 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以84%的产率得到5,7-dichloro-2-phenylbenzofuran
  参考文献：
  名称：

  Copper-catalyzed decarboxylative intramolecular C–O coupling: synthesis of 2-arylbenzofuran from 3-arylcoumarin

  摘要：

  建立了一种铜催化的脱羧分子内 CâO 偶联反应。在氯化铜/1,10-菲罗啉存在的有氧条件下，以 3-芳基香豆素为原料一锅制备了多种 2-芳基苯并呋喃，收率从 26% 到 84%不等。

  DOI：

  10.1039/c3ra46414h
• 作为产物：
  描述：

  苯乙酸 、 3,5-二氯水杨醛 在 乙酸酐 、 三乙胺 作用下， 反应 8.0h， 以54%的产率得到6,8-dichloro-3-phenylcoumarin
  参考文献：
  名称：

  3-Arylcoumarins: Synthesis and potent anti-inflammatory activity

  摘要：

  Chronic inflammation is the persistent and excessive immune response and can lead to a variety of diseases. Aiming to discover new compounds with anti-inflammatory activity, we report herein the synthesis and biological evaluation of 3-arylcoumarins. Thirty five 3-arylcoumarins were prepared through Perkin condensation and further acid-promoted hydrolysis if necessary. In lipopolysaccharide-activated mouse macrophage RAW264.7 cells, 6,8-dichloro-3-(2-methoxyphenyl) coumarin (16) and 6-bromo-8-methoxy-3-(3-methoxyphenyl) coumarin (25) exhibited nitric oxide production inhibitory activity with the IC50 values of 8.5 mu M and 6.9 mu M, respectively, providing a pharmacological potential as anti-inflammatory agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.033

文献信息

• Copper-catalyzed decarboxylative intramolecular C–O coupling: synthesis of 2-arylbenzofuran from 3-arylcoumarin
  作者：Wen-Chen Pu、Guan-Min Mu、Guo-Lin Zhang、Chun Wang

  DOI：10.1039/c3ra46414h

  日期：——

  A copper-catalyzed decarboxylative intramolecular C–O coupling reaction was established. Under aerobic conditions in the presence of cupric chloride/1,10-phenathroline, a variety of 2-arylbenzofurans were prepared from 3-arylcoumarins in one-pot with yields from 26% to 84%.

  建立了一种铜催化的脱羧分子内 CâO 偶联反应。在氯化铜/1,10-菲罗啉存在的有氧条件下，以 3-芳基香豆素为原料一锅制备了多种 2-芳基苯并呋喃，收率从 26% 到 84%不等。
• Recyclable palladium-catalyzed cyclocarbonylation between benzyl chlorides and salicylic aldehydes towards coumarins
  作者：Yan Zhou、Zebiao Zhou、Siqi Liu、Mingzhong Cai

  DOI：10.1016/j.mcat.2022.112404

  日期：2022.6
• 2-Phenylbenzo[ b ]furans: Synthesis and promoting activity on estrogen biosynthesis
  作者：Wenchen Pu、Yun Yuan、Danfeng Lu、Xin Wang、Hanwei Liu、Chun Wang、Fei Wang、Guolin Zhang

  DOI：10.1016/j.bmcl.2016.10.013

  日期：2016.11

  2-phenylbenzo[b]furan glycosides could promote estrogen biosynthesis. To find high active 2-phenylbenzo[b]furans, fifty-four 2-phenylbenzo[b]furans were prepared via four strategies according to corresponding substrate scopes. Biological evaluation in HEK293A cells showed that some compounds exhibited promotive activity on estrogen biosynthesis. 2-(4-Chlorophenyl)-7-methoxybenzo[b]furan possessed the

  雌激素的生物合成对人类的许多生理过程至关重要。雌激素水平异常与多种疾病密切相关，包括乳腺癌和骨质疏松症。以前我们发现2-苯基苯并[b]呋喃糖苷可以促进雌激素的生物合成。为了找到高活性的2-苯基苯并[b]呋喃，根据相应的底物范围，通过四种策略制备了五十四种2-苯基苯并[b]呋喃。HEK293A细胞的生物学评估表明，某些化合物对雌激素的生物合成具有促进作用。2-（4-氯苯基）-7-甲氧基苯并[b]呋喃具有最高的活性，EC50值为14.68μM。此外，这些化合物不会影响HEK292A细胞中的芳香化酶表达，
• 3-Arylcoumarins: Synthesis and potent anti-inflammatory activity
  作者：Wenchen Pu、Yuan Lin、Jianshuo Zhang、Fei Wang、Chun Wang、Guolin Zhang

  DOI：10.1016/j.bmcl.2014.10.033

  日期：2014.12

  Chronic inflammation is the persistent and excessive immune response and can lead to a variety of diseases. Aiming to discover new compounds with anti-inflammatory activity, we report herein the synthesis and biological evaluation of 3-arylcoumarins. Thirty five 3-arylcoumarins were prepared through Perkin condensation and further acid-promoted hydrolysis if necessary. In lipopolysaccharide-activated mouse macrophage RAW264.7 cells, 6,8-dichloro-3-(2-methoxyphenyl) coumarin (16) and 6-bromo-8-methoxy-3-(3-methoxyphenyl) coumarin (25) exhibited nitric oxide production inhibitory activity with the IC50 values of 8.5 mu M and 6.9 mu M, respectively, providing a pharmacological potential as anti-inflammatory agents. (C) 2014 Elsevier Ltd. All rights reserved.