6-bromo-3-cinnamoyl-2H-chromen-2-one | 80467-51-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 6-bromo-3-cinnamoyl-2H-chromen-2-one
• 英文别名: 6-Bromo-3-(3-phenylprop-2-enoyl)chromen-2-one
• CAS: 80467-51-2
• 化学式: C₁₈H₁₁BrO₃
• mdl: MFCD00768691
• 分子量: 355.188
• InChiKey: HMEIKRHCVLVHEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-3-cinnamoyl-2H-chromen-2-one 、 2-氨基苯硫醇 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  A Facile One Pot Synthesis of 2-Aryl-4-[2H-2-oxo-[1]benzopyran-3-yl] 2,3-dihydro and 2,5-Dihydro-1,5-benzothiazepines

  摘要：

  3-acetyl coumarins on condensation with various aromatic aldehydes in the presence of piperidine gave corresponding chalcones in a solid state under solvent free conditions. These chalcones are isolated and characterized. The in-situ-formed chalcones (1) are also converted into corresponding 2-aryl-4-[2H-2oxo[1]benzopyran-3-yl]-2,3-dihydro (3) and 2,5-dihydro-1,5-benzothiazepines (4) in one step by interacting with orthoamino thiophenol. Both the 2,3-dihydro (3) and 2,5-dihydrobenzothiazepines ( 4) have been converted into same tetrahydrobenzothiazepine (5). Finally, the tetrahydrobenzo thiazepine (5) is converted into its acetyl derivative (11). The structures of the title compounds have been confirmed on the basis of their microanalytical, IR, H-1 NMR, and mass spectral data.

  DOI：

  10.1080/104265091001326
• 作为产物：
  描述：

  5-溴水杨醛 在 哌啶 、 吡啶 作用下， 反应 0.83h， 生成 6-bromo-3-cinnamoyl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis, Thermal, and Biological Studies of Newly Synthesized Cu(II) Complexes With Ciprofloxacin Based on Bromo-Coumarins Derivatives

  摘要：

  The authors describe synthesis, characterization, and biological evaluation of Cu(II) complexes. Characterization of ligands has been carried out by elemental analysis, melting point, mass spectra, (H-1 & C-13) NMR, and FT-IR, while structure of metal complexes was confirmed by electronic spectra and FAB-mass spectral studies. Spectral studies confirm ligands is mono functional bidentate and octahedral environment around metal ions. Thermal behavior of Cu(II) complexes were investigated by means of TGA and magnetic measurements. The kinetic parameters are reported using the Freeman-Carroll method. Complexes were found significant potent antimicrobial and antioxidant activities compared to parent ligands employed for complexation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry to view the supplemental file.

  DOI：

  10.1080/15533174.2012.754763

文献信息

• Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-<i>c</i>]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives
  作者：Geng-Hua Chang、Chein-Yi Wang、G. Madhusudhan Reddy、Yi-Ling Tsai、Wenwei Lin

  DOI：10.1021/acs.joc.6b02041

  日期：2016.10.21

  benzopyrano[3,4-c]pyrrolidine derivatives via organocatalyzed [3 + 2] cycloaddition has been achieved. Cinchona alkaloid-derived organocatalysts as Brønsted bases have been examined for this asymmetric cycloaddition of o-hydroxy aromatic aldimines with 3-substituted coumarins. An unexpected rearrangement of the quaternary acyl moiety in the products resulted in an in situ protection of the o-hydroxy group.

  通过有机催化的[3 + 2]环加成反应实现了对苯并吡喃并[3,4- c ]吡咯烷衍生物的对映选择性合成。已经检查了金鸡纳生物碱衍生的有机催化剂作为布朗斯台德碱，该邻位羟基芳族醛亚胺与3-取代的香豆素的不对称环加成反应。产物中季酰基部分的意外重排导致原位保护邻羟基。
• Multiple heating rate kinetic parameters, thermal, X-ray diffraction studies of newly synthesized octahedral copper complexes based on bromo-coumarins along with their antioxidant, anti-tubercular and antimicrobial activity evaluation
  作者：Ketan S. Patel、Jiten C. Patel、Hitesh R. Dholariya、Kanuprasad D. Patel

  DOI：10.1016/j.saa.2012.05.057

  日期：2012.10

  Series of new Cu(II) complexes were synthesized by classical thermal technique. The biologically potent ligands (L) were prepared by refluxing 6-brom 3-acetyl coumarin with aldehydes in the presence of piperidine in ethanol. The Cu(II) complexes have been synthesized by mixing an aqueous solution of Cu(NO(3))(2) in 1:1 molar ratios with ethanolic bidentate ligands and Clioquinol. The structures of

  通过经典的热技术合成了一系列新的Cu（II）配合物。通过在乙醇中的哌啶存在下使6-溴3-乙酰基香豆素与醛回流，可制备具有生物活性的配体（L）。Cu（II）配合物已通过将Cu（NO（3））（2）的水溶液以1：1摩尔比与乙醇二齿配体和Clioquinol混合来合成。分别通过元素分析，FT-IR，（1）H NMR，（13）C NMR，质谱和粉末X射线衍射研究对配体及其铜配合物的结构进行了研究和确认。通过热重分析，差示热重分析，差示扫描量热法，电子光谱和磁测量方法研究了新合成的混合配体Cu（II）配合物的热行为。在不同的加热速率（2.5-20°C min（-1））下对Cu（II）配合物进行DSC实验的动态扫描。通过基辛格和小泽的方法获得的所有复合物的第二步降解动力学参数均一致。在这些研究的基础上，很明显，通过OO和ON供体系统，配体以一元二齿模式与金属原子配位。因此，已经提出了用于金属配合物的六配
• Synthesis and molecular docking study of novel coumarin derivatives containing 4,5-dihydropyrazole moiety as potential antitumor agents
  作者：Xin-Hua Liu、Hui-Feng Liu、Jin Chen、Yang Yang、Bao-An Song、Lin-Shan Bai、Jing-Xin Liu、Hai-Liang Zhu、Xing-Bao Qi

  DOI：10.1016/j.bmcl.2010.08.017

  日期：2010.10

  A series of novel coumarin derivatives containing 4,5-dihydropyrazole moiety as potential telomerase inhibitors were synthesized. The bioassay tests show that compound 3d exhibited potentially high activity against human gastric cancer cell SGC-7901 with IC50 value of 2.69 ± 0.60 μg/mL. All title compounds were assayed for telomerase inhibition by a modified TRAP assay, the results show that compounds

  合成了一系列含有4,5-二氢吡唑部分作为潜在的端粒酶抑制剂的香豆素衍生物。生物测定测试表明，化合物3d对人胃癌细胞SGC-7901表现出潜在的高活性，IC 50值为2.69±0.60μg/ mL。通过改良的TRAP分析法检测了所有标题化合物的端粒酶抑制作用，结果表明化合物3d和3f可以强烈抑制端粒酶，IC 50值分别为2.0±0.07和1.8±0.35μM。进行对接模拟以将化合物3d定位于端粒酶（3DU6）活性位点，以确定可能的结合模型。
• Younes, M. El-Garby; El-Kady, M.; Essawy, A. I., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 9, p. 747 - 750
  作者：Younes, M. El-Garby、El-Kady, M.、Essawy, A. I.、Mohamed, A. Y.

  DOI：——

  日期：——
• Synthesis, Thermal, and Biological Studies of Newly Synthesized Cu(II) Complexes With Ciprofloxacin Based on Bromo-Coumarins Derivatives
  作者：Ketan S. Patel、Jiten C. Patel、Hitesh R. Dholariya、Kanuprasad D. Patel

  DOI：10.1080/15533174.2012.754763

  日期：2013.9.14

  The authors describe synthesis, characterization, and biological evaluation of Cu(II) complexes. Characterization of ligands has been carried out by elemental analysis, melting point, mass spectra, (H-1 & C-13) NMR, and FT-IR, while structure of metal complexes was confirmed by electronic spectra and FAB-mass spectral studies. Spectral studies confirm ligands is mono functional bidentate and octahedral environment around metal ions. Thermal behavior of Cu(II) complexes were investigated by means of TGA and magnetic measurements. The kinetic parameters are reported using the Freeman-Carroll method. Complexes were found significant potent antimicrobial and antioxidant activities compared to parent ligands employed for complexation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry to view the supplemental file.