3-(4-(trifluoromethyl)phenyl)chroman-4-one | 1220452-68-5

• 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: 3-(4-(trifluoromethyl)phenyl)chroman-4-one
• 英文别名: 3-[4-(trifluoromethyl)phenyl]-2,3-dihydrochromen-4-one
• CAS: 1220452-68-5
• 化学式: C₁₆H₁₁F₃O₂
• 分子量: 292.257
• InChiKey: GHQXDYKJXNHFKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-乙炔基-α,α,α-三氟甲苯 、 水杨醛 在 gold(I) cyanide 、 三丁基膦 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以19.6%的产率得到3-(4-(trifluoromethyl)phenyl)chroman-4-one
  参考文献：
  名称：

  Investigation of fluorinated and bifunctionalized 3-phenylchroman-4-one (isoflavanone) aromatase inhibitors

  摘要：

  Fluorinated isoflavanones and bifunctionalized isoflavanones were synthesized through a one-step gold(I)-catalyzed annulation reaction. These compounds were evaluated for their in vitro inhibitory activities against aromatase in a fluorescence-based enzymatic assay. Selected compounds were tested for their anti-proliferative effects on human breast cancer cell line MCF-7. Compounds 6-methoxy-3-(pyridin-3-yl)chroman-4-one (3c) and 6-fluoro-3-(pyridin-3-yl)chroman-4-one (3e) were identified as the most potent aromatase inhibitors with IC50 values of 2.5 mu M and 0.8 mu M. Therefore, these compounds have great potential for the development of pharmaceutical agents against breast cancer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.045

文献信息

• Palladium-Catalyzed Direct Arylation of 4-Chromanones: Selective Synthesis of Racemic Isoflavanones and 3,3-Diaryl-4-chromanones
  作者：Fabio Bellina、Tiziana Masini、Renzo Rossi

  DOI：10.1002/ejoc.200901356

  日期：2010.3

  yields and with high selectivity by Pd-catalyzed direct C-3 arylation of 3-unsubstituted 4-chromanones with aryl bromides with the aid of a Pd 2 (dba) 3 /tBu 3 PHBF 4 catalyst system in the presence of KHCO 3 as the base in a dioxane/water mixture (4:1). This catalyst system has also been employed in an unprecedented synthesis of 3,3-diaryl-4-chromanones through direct arylation of 4-chromanones in

  通过 Pd 催化的 3-未取代 4-色满酮与芳基溴化物的直接 C-3 芳基化，借助 Pd 2 (dba ) 3 /tBu 3 PHBF 4 催化剂体系，在二恶烷/水混合物 (4:1) 中，KHCO 3 作为碱存在。该催化剂体系还用于通过 4-色满酮在水中的直接芳基化，以前所未有的方式合成 3,3-二芳基-4-色满酮。
• Investigation of fluorinated and bifunctionalized 3-phenylchroman-4-one (isoflavanone) aromatase inhibitors
  作者：Erica Amato、Tony Bankemper、Rebecca Kidney、Thuy Do、Alma Onate、Fathima Shazna Thowfeik、Edward J. Merino、Stefan Paula、Lili Ma

  DOI：10.1016/j.bmc.2013.11.045

  日期：2014.1

  Fluorinated isoflavanones and bifunctionalized isoflavanones were synthesized through a one-step gold(I)-catalyzed annulation reaction. These compounds were evaluated for their in vitro inhibitory activities against aromatase in a fluorescence-based enzymatic assay. Selected compounds were tested for their anti-proliferative effects on human breast cancer cell line MCF-7. Compounds 6-methoxy-3-(pyridin-3-yl)chroman-4-one (3c) and 6-fluoro-3-(pyridin-3-yl)chroman-4-one (3e) were identified as the most potent aromatase inhibitors with IC50 values of 2.5 mu M and 0.8 mu M. Therefore, these compounds have great potential for the development of pharmaceutical agents against breast cancer. (C) 2013 Elsevier Ltd. All rights reserved.