3-(4-acetylphenyl)-2H-chromen-2-one

• 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-acetylphenyl)-2H-chromen-2-one
• 英文别名: 3-(4-Acetylphenyl)-2h-chromen-2-one；3-(4-acetylphenyl)chromen-2-one
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: YBAIMHSHQLCASN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  3-(4-acetylphenyl)-2H-chromen-2-one 在 溴 、 溶剂黄146 作用下， 以71%的产率得到3-[4-(2-bromoacetyl)phenyl]-2H-chromen-2-one
  参考文献：
  名称：

  New biscyanine dye based on 1-{2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]ethyl}-4-methylpyridinium bromide. Electron transitions and electronic spectra

  摘要：

  New biscyanine dye, 4-{2-[4-(dimethylamino)phenyl]ethenyl}-1-{2-[4-(dimethylamino)phenyl]-1-[4-(2-oxo-2H-chromen-3-yl)benzoyl]ethenyl}pyridinium bromide, has been prepared via condensation of 4-dimethylaminobenzaldehyde with 4-methyl-1-{2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]ethyl}pyridinium bromide. The latter has been synthesized via the Meerwein reaction of coumarin with 4-acetylphenyldiazonium chloride with subsequent bromination and quaternization of the formed alpha-bromoketone under the action of 4-methylpyridine. Electronic spectra are analyzed, and quantum-chemical simulation of possible isomers of the biscyanine dye has been performed.

  DOI：

  10.1134/s1070363214110127
• 作为产物：
  描述：

  水杨醛 在 potassium tert-butylate 、 氧气 、 copper(l) chloride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 19.0h， 生成 3-(4-acetylphenyl)-2H-chromen-2-one
  参考文献：
  名称：

  N-甲苯磺酰N和末端炔烃的 可见光驱动铜催化有氧氧化级联环化：3-芳基香豆素的区域选择性合成†

  摘要：

  我们提出了可持续的，直观的，高度区域选择性的，可见光驱动的铜催化的N-甲苯磺酰with与末端炔烃的有氧氧化级联环化反应，以在室温下制备3-芳基香豆素。这种操作简单的方法已成功应用于各种N-甲苯磺酰hydr和炔烃（49个实例），并且进展顺利，可提供具有生物活性的化合物，例如单胺氧化酶B（MAO-B）抑制剂和辣根过氧化物酶（HRP）抑制剂，在温和的条件下具有令人满意的产量。此外，机理研究表明，反应是通过铜进行的（II18 O 2同位素标记实验证明）-超氧或-过氧配合物介导的末端炔烃的氧化环化反应。

  DOI：

  10.1039/c9cc01801h

文献信息

• KMnO₄/AcOH-mediated C3-selective direct arylation of coumarins with arylboronic acids
  作者：Jin-Wei Yuan、Liang-Ru Yang、Qiu-Yue Yin、Pu Mao、Ling-Bo Qu

  DOI：10.1039/c6ra04787d

  日期：——

  dehydrogenative direct radical arylation of coumarins with arylboronic acids to afford 3-arylcoumarin derivatives is described. A similar reaction system is also applicable to the 3-arylation of quinolinone derivatives. These KMnO4/AcOH-mediated coupling reactions occur regioselectively at the C3 position of coumarins and quinolinones. Some notable features of this method are high efficiency, moderate

  描述了一种有效的方案，用于香豆素与芳基硼酸的KMnO 4 / AcOH介导的脱氢直接自由基芳基化，以提供3-芳基香豆素衍生物。类似的反应系统也适用于喹啉酮衍生物的3-芳基化。这些KMnO 4 / AcOH介导的偶联反应在香豆素和喹啉酮的C3位置区域选择性地发生。该方法的一些显着特征是效率高，产量中等到良好以及广泛的群体耐受性。
• Synthesis of nitrogen heterocycles underlain by application of 3-(4-Acetyl[phenyl)-2H-coumarin
  作者：O. V. Skripskaya、N. O. Feilo、A. O. Neshchadin、O. V. Elenich、R. Z. Lytvyn、N. D. Obushak、P. I. Yagodinets

  DOI：10.1134/s1070428013110158

  日期：2013.11

  3-(4-Acetylphenyl)-2H-chromen-2-one was obtained from 4-acetylphenyldiazonium chloride in the conditions of Meerwein reaction. Reactions of 3-[4-(2-bromoacetyl)phenyl]-2H-chromen-2-one with pyridine, 4-methylpyridine, quinoline, benzo[f]quinoline, and triphenylphosphine afforded quaternary salts, and with thioacetamide, thiourea, 2-aminopyridine, 2-aminopyrimidine, and 6-aminopurine provided the corresponding derivatives of thiazole, imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, imidazo[2,1-i]purine. In the reaction of the same bromo derivative with thiosemicarbazide and aromatic aldehydes a thiazole ring is built and the corresponding hydrazones are formed.
• Ranjith, Choorikkat; Paul, Nidhin; Vijayan, Asian Journal of Chemistry, 2011, vol. 23, # 1, p. 235 - 238
  作者：Ranjith, Choorikkat、Paul, Nidhin、Vijayan

  DOI：——

  日期：——
• New biscyanine dye based on 1-{2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]ethyl}-4-methylpyridinium bromide. Electron transitions and electronic spectra
  作者：O. V. Yelenich、O. V. Skrypska、R. Z. Lytvyn、A. O. Neshchadin、M. D. Obushak、A. D. Kachkovskii、P. I. Yagodinets

  DOI：10.1134/s1070363214110127

  日期：2014.11

  New biscyanine dye, 4-2-[4-(dimethylamino)phenyl]ethenyl}-1-2-[4-(dimethylamino)phenyl]-1-[4-(2-oxo-2H-chromen-3-yl)benzoyl]ethenyl}pyridinium bromide, has been prepared via condensation of 4-dimethylaminobenzaldehyde with 4-methyl-1-2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]ethyl}pyridinium bromide. The latter has been synthesized via the Meerwein reaction of coumarin with 4-acetylphenyldiazonium chloride with subsequent bromination and quaternization of the formed alpha-bromoketone under the action of 4-methylpyridine. Electronic spectra are analyzed, and quantum-chemical simulation of possible isomers of the biscyanine dye has been performed.
• Visible-light-driven copper-catalyzed aerobic oxidative cascade cyclization of <i>N</i>-tosylhydrazones and terminal alkynes: regioselective synthesis of 3-arylcoumarins
  作者：Ayyakkannu Ragupathi、Arunachalam Sagadevan、Vaibhav Pramod Charpe、Chun-Cheng Lin、Jih-Ru Hwu、Kuo Chu Hwang

  DOI：10.1039/c9cc01801h

  日期：——

  first example of sustainable, intuitive, highly regioselective, visible-light-driven copper catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones with terminal alkynes for the preparation of 3-arylcoumarins at room temperature. This operationally simple methodology has been successfully applied to a wide range of N-tosylhydrazones and alkynes (49 examples), and proceeds well to afford biologically

  我们提出了可持续的，直观的，高度区域选择性的，可见光驱动的铜催化的N-甲苯磺酰with与末端炔烃的有氧氧化级联环化反应，以在室温下制备3-芳基香豆素。这种操作简单的方法已成功应用于各种N-甲苯磺酰hydr和炔烃（49个实例），并且进展顺利，可提供具有生物活性的化合物，例如单胺氧化酶B（MAO-B）抑制剂和辣根过氧化物酶（HRP）抑制剂，在温和的条件下具有令人满意的产量。此外，机理研究表明，反应是通过铜进行的（II18 O 2同位素标记实验证明）-超氧或-过氧配合物介导的末端炔烃的氧化环化反应。