4-oxo-2-phenyl-4H-chromen-5-yl trifluoromethanesulfonate | 920286-84-6

• 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: 4-oxo-2-phenyl-4H-chromen-5-yl trifluoromethanesulfonate
• 英文别名: 2-Phenyl-5-(trifluoromethylsulfonyloxy)-4H-1-benzopyran-4-one；(4-oxo-2-phenylchromen-5-yl) trifluoromethanesulfonate
• CAS: 920286-84-6
• 化学式: C₁₆H₉F₃O₅S
• 分子量: 370.306
• InChiKey: PKOKYILFEMKIPB-UHFFFAOYSA-N

物化性质

• 沸点：
  474.0±45.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-oxo-2-phenyl-4H-chromen-5-yl trifluoromethanesulfonate 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 二异丙胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.67h， 生成 5-ethynyl-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  Ethynylflavones, Highly Potent, and Selective Inhibitors of Cytochrome P450 1A1

  摘要：

  The flavone backbone is a well-known pharmacophore present in a number of substrates and inhibitors of various P450 enzymes. In order to find highly potent and novel P450 family I enzyme inhibitors, an acetylene group was incorporated into six different positions of flavone. The introduction of an acetylene group at certain locations of the flavone backbone lead to time-dependent inhibitors of P450 1A1. 3'-Ethynylflavone, 4'-ethynylflavone, 6-ethynylflavone, and 7-ethynylflavone (K-I values of 0.035-0.056 mu M) show strong time-dependent inhibition of P450 1A1, while 5-ethynylflavone (K-I value of 0.51 mu M) is a moderate time-dependent inhibitor of this enzyme. Meanwhile, 4'-ethynylflavone and 6-ethynylflavone are highly selective inhibitors toward this enzyme. Especially, 6-ethynylflavone possesses a K-i value of 0.035 mu M for P450 1A1 177- and 15-fold lower than those for P450s 1A2 and 1B1, respectively. The docking postures observed in the computational simulations show that the orientation of the acetylene group determines its capability to react with P450s 1A1 and 1A2. Meanwhile, conformational analysis indicates that the shape of an inhibitor determines its inhibitory selectivity toward these enzymes.

  DOI：

  10.1021/tx5001865
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.75h， 生成 4-oxo-2-phenyl-4H-chromen-5-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Microwave enhanced palladium catalysed coupling reactions: A diversity-oriented synthesis approach to functionalised flavones

  摘要：

  引入了微波增强的多样性导向合成（MEDOS），采用钯催化的方案，作为系统修饰小分子合成的一种强大新策略，并通过功能化黄酮的应用进行了突出展示。

  DOI：

  10.1039/b610734f

文献信息

• [EN] HETEROCYCLYL POLYMETHINE IR CHROMOPHORES<br/>[FR] CHROMOPHORES IR À BASE DE POLYMÉTHINE HÉTÉROCYCLYLE
  申请人：UNIV CALIFORNIA

  公开号：WO2020118116A1

  公开（公告）日：2020-06-11

  The present disclosure provides NIR- and SWIR-active small molecule polymethine dyes with improved properties for use in optical imaging, photothermal therapy, and photodynamic therapy.

  本公开提供了具有改进性能的近红外和短波红外活性小分子聚甲啉染料，用于光学成像、光热疗法和光动力疗法。
• Regioselective synthesis of flavone derivatives via DMAP-catalyzed cyclization of o-alkynoylphenols
  作者：Masahito Yoshida、Yuta Fujino、Koya Saito、Takayuki Doi

  DOI：10.1016/j.tet.2011.09.063

  日期：2011.12

  A catalytic amount of DMAP promoted cyclization of o-alkynoylphenols via a 6-endo cyclization mode leading to flavone derivatives in high yields without forming 5-exo cyclized aurone derivatives. Utilizing this method, methoxy substituted flavone and alkyl substituted γ-benzopyranone derivatives were synthesized.

  DMAP催化量的促进环化ö -alkynoylphenols经由6-内环化模式，导致高产量黄酮衍生物，而不形成5-外型环化噢哢衍生物。利用这种方法，合成了甲氧基取代的黄酮和烷基取代的γ-苯并吡喃酮衍生物。
• Photophysical Tuning of Shortwave Infrared Flavylium Heptamethine Dyes via Substituent Placement
  作者：Monica Pengshung、Jingbai Li、Fatemah Mukadum、Steven A. Lopez、Ellen M. Sletten

  DOI：10.1021/acs.orglett.0c02213

  日期：2020.8.7

  Optical imaging in the shortwave infrared region (SWIR, 1000–2000 nm) provides high-resolution images in complex systems. Here we explore substituent placement on dimethylamino flavylium polymethine dyes, a class of SWIR fluorophores. We find that the position of the substituent significantly affects the λmax and fluorescence quantum yield. Quantum-mechanical calculations suggest that steric clashes

  短波红外区域（SWIR，1000-2000 nm）的光学成像可在复杂系统中提供高分辨率图像。在这里，我们探索了二甲氨基黄鎓多甲川染料（一类 SWIR 荧光团）上的取代基位置。我们发现取代基的位置显着影响 λ max和荧光量子产率。量子力学计算表明空间冲突控制 π 共轭的程度。这些见解为开发用于增强 SWIR 成像的荧光团提供了设计原则。
• Efficient Synthesis of Biflavones Having A Ring-A Ring of Two Flavone Units Using Suzuki Cross-Coupling Reactions
  作者：Hiroto Nakano、Yukio Hoshino、Haruo Matsuyama、Yoshihito Kohari

  DOI：10.3987/com-10-s(e)36

  日期：——

  Biflavones having a A ring-A ring of two flavone units were easily prepared by using Suzuki cross-coupling reaction of borylated flavones with bromoflavones or flavone-5-triflate in good to excellent yields.
• Ethynylflavones, Highly Potent, and Selective Inhibitors of Cytochrome P450 1A1
  作者：Navneet Goyal、Jiawang Liu、La’Nese Lovings、Patrick Dupart、Shannon Taylor、Sydni Bellow、Lydia Mensah、Erika McClain、Brandan Dotson、Jayalakshmi Sridhar、Xiaoyi Zhang、Ming Zhao、Maryam Foroozesh

  DOI：10.1021/tx5001865

  日期：2014.8.18

  The flavone backbone is a well-known pharmacophore present in a number of substrates and inhibitors of various P450 enzymes. In order to find highly potent and novel P450 family I enzyme inhibitors, an acetylene group was incorporated into six different positions of flavone. The introduction of an acetylene group at certain locations of the flavone backbone lead to time-dependent inhibitors of P450 1A1. 3'-Ethynylflavone, 4'-ethynylflavone, 6-ethynylflavone, and 7-ethynylflavone (K-I values of 0.035-0.056 mu M) show strong time-dependent inhibition of P450 1A1, while 5-ethynylflavone (K-I value of 0.51 mu M) is a moderate time-dependent inhibitor of this enzyme. Meanwhile, 4'-ethynylflavone and 6-ethynylflavone are highly selective inhibitors toward this enzyme. Especially, 6-ethynylflavone possesses a K-i value of 0.035 mu M for P450 1A1 177- and 15-fold lower than those for P450s 1A2 and 1B1, respectively. The docking postures observed in the computational simulations show that the orientation of the acetylene group determines its capability to react with P450s 1A1 and 1A2. Meanwhile, conformational analysis indicates that the shape of an inhibitor determines its inhibitory selectivity toward these enzymes.