2-(4-bromophenyl)-3H-benzo[f]chromen-3-one | 303205-70-1

• 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: 2-(4-bromophenyl)-3H-benzo[f]chromen-3-one
• 英文别名: 3-(4-bromophenyl)-benzo[5,6]coumarin；3-(4-bromophenyl)benzo[5,6]coumarin；2-(4-bromo-phenyl)-benzo[f]chromen-3-one；2-(4-Brom-phenyl)-benzo[f]chromen-3-on；3-(p-bromophenyl)benzo[5,6]coumarin；2-(4-Bromophenyl)-3H-naphtho[2,1-b]pyran-3-one；2-(4-bromophenyl)benzo[f]chromen-3-one
• CAS: 303205-70-1
• 化学式: C₁₉H₁₁BrO₂
• 分子量: 351.199
• InChiKey: RNEPXAQELHEKOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• 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：

  2-(4-bromophenyl)-3H-benzo[f]chromen-3-one 、 2-(蒽-9-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼烷 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以77%的产率得到3-(4-(anthracen-10-yl)phenyl)-benzo[5,6]coumarin
  参考文献：
  名称：

  Synthesis, crystal structure and photoluminescence of 3-(4-(anthracen-10-yl)phenyl)-benzo[5,6]coumarin

  摘要：

  A new coumarin derivative, 3-(4-(anthracen-10-yl)phenyl)-benzo[5,6]coumarin, was synthesized and characterized by FT-IR, H-1 NMR, element analysis and single crystal X-ray crystallography. The dihedral angle of benzo[5,6]coumarin ring and phenyl group is 36.15 degrees, and the dihedral angle of phenyl group and anthracene skeleton is 89.37 degrees. The UV-vis absorption and photoluminescence of the Compound were discussed. The result shown that the compound exhibits high fluorescence quantum yield (00, large Stokes shift and green emission (508 nm). The molecular structure of the compound was optimized using density functional theory (DFT) at B3LYP/6-31G(d) level, and the HOMO and LUMO levels of the compound were deduced. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2009.10.034
• 作为产物：
  描述：

  2-(4-bromo-phenyl)-3-(2-methoxy-[1]naphthyl)-acrylonitrile 在 吡啶盐酸盐 作用下， 生成 2-(4-bromophenyl)-3H-benzo[f]chromen-3-one
  参考文献：
  名称：

  Buu-Hoi et al., Journal of the Chemical Society, 1951, p. 2307

  摘要：

  DOI：

文献信息

• A transition-metal-free fast track to flavones and 3-arylcoumarins
  作者：Mostafa Golshani、Mehdi Khoobi、Nafiseh Jalalimanesh、Farnaz Jafarpour、Alireza Ariafard

  DOI：10.1039/c7cc02107k

  日期：——

  The procedure consists of a sequence of some reactions including an arylation/decarboxylation cascade and proceeds well in aqueous media to afford biologically interesting flavones and 3-arylcoumarins. This method exhibited excellent selectivity and functional group tolerance under mild conditions. The reaction also showed perfect efficacy for the preparation of styryl coumarins.

  使用K 2 S 2 O 8，实现了色农酮与芳基硼酸的高度区域选择性和无过渡金属的一锅芳基化反应。该程序由一系列反应组成，包括芳基化/脱羧级联，并在水性介质中进行得很好，从而提供了生物学上令人感兴趣的黄酮和3-芳基香豆素。该方法在温和条件下显示出极好的选择性和官能团耐受性。该反应还显示出制备苯乙烯基香豆素的完美功效。
• FLUORESCENT AGENT HAVING ETHYNYL GROUP
  申请人：Mizuno Kazuhiko

  公开号：US20100298573A1

  公开（公告）日：2010-11-25

  There are provided novel fluorescent agents, such as pyrazoline compounds represented by formula (I): (wherein R 1 , R 2 and R 3 are as defined in the specification), having an ethynyl group in the molecule, which have high absorptivity in the ultraviolet-visible short wavelength range (for example, 350 nm-420 nm).

  提供了新型荧光试剂，例如由式(I)代表的吡唑啉化合物：（其中R1、R2和R3如规范中定义），分子中具有乙炔基团，在紫外可见短波长范围（例如，350纳米至420纳米）具有很高的吸收性。
• Base-promoted synthesis of coumarins from salicylaldehydes and aryl-substituted 1,1-dibromo-1-alkenes under transition-metal-free conditions
  作者：Jianming Liu、Xin Zhang、Lijun Shi、Muwen Liu、Yuanyuan Yue、Fuwei Li、Kelei Zhuo

  DOI：10.1039/c4cc04377d

  日期：——

  Facile synthesis of coumarin via the tandem reaction of salicylaldehyde with aryl-substituted 1,1-dibromo-1-alkene was developed. This new protocol proceeds smoothly under mild and transition-metal-free conditions, it allows rapid access to coumarins containing various heteroatoms that are more difficult to prepare by traditional methods. Based on the isolated intermediate of 4-(diethylamino)-3-phenylchroman-2-one and detailed mechanistic studies, a credible tandem pathway was proposed.

  开发了一种简单的合成香豆素的方法，利用水杨醛与芳基取代的1,1-二溴-1-烯的串联反应。该新方法在温和且无过渡金属的条件下顺利进行，能够快速合成含有多种杂原子的香豆素，而这些香豆素通过传统方法更难制备。基于分离得到的中间体4-(二乙氨基)-3-苯基克罗莫酮和详细的机理研究，提出了一条可信的串联反应路径。
• US7521567B2
  申请人：——

  公开号：US7521567B2

  公开（公告）日：2009-04-21
• Buu-Hoi et al., Journal of the Chemical Society, 1951, p. 2307
  作者：Buu-Hoi et al.

  DOI：——

  日期：——