2-amino-4-(4-methoxyphenyl)-4H-chromene-3-carbonitrile | 119825-04-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2-amino-4-(4-methoxyphenyl)-4H-chromene-3-carbonitrile
• CAS: 119825-04-6
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: HRVQDWSWMJOTOS-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C
• 沸点：
  480.9±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-(4-methoxyphenyl)-4H-chromene-3-carbonitrile 、 尿素 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以58%的产率得到4-amino-5-(4-methoxyphenyl)-1,5-dihydro-2H-chromeno[2,3-d]pyrimidine-2-one
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation of antitubercular and antimicrobial activity of some novel pyranopyrimidines

  摘要：

  The clinical significance of pyran and pyrimidine condensed systems and the raise in problem of multidrug resistant bacterial pathogens has directed us to synthesize pyranopyrimidine derivatives via the reactions of the versatile, 2-amino-4-(4-methoxyphenyl)-4H-substitutedchromene-3-carbonitrile with the appropriate reagents. The newly synthesized compounds were characterized by IR, H-1 NMR,C-13 NMR, Mass spectra and Elemental analysis. The compounds were evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H(37)Rv [ATCC-27294] and antibacterial activity against Staphylococcus aureus [ATCC-25923] and Streptococcus pyogenes [MTCC-443] as Gram-positive, Escherichia coli [ATCC-25922] and Pseudomonas aeruginosa [MTCC-441] as Gram-negative bacterial strains and antifungal activity against Aspergillus niger [MTCC-282]. Several derivatives exhibited pronounced antitubercular and antimicrobial activities. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.014
• 作为产物：
  描述：

  (4-甲氧基苄烯)丙二腈 、 苯酚 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以85%的产率得到2-amino-4-(4-methoxyphenyl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Elagamey, Abdel Ghani A.; Sawllim, Salah Z.; El-Taweel, Fathy M.A., Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 7, p. 1534 - 1538

  摘要：

  DOI：

文献信息

• Facile Protocol for the Synthesis of 2-Amino-4H-Chromene Derivatives using Choline Chloride/Urea
  作者：Behrooz Maleki、Reza Tayebee、Ali Khoshsima、Farshid Ahmadpoor

  DOI：10.1080/00304948.2020.1833623

  日期：2021.1.2

  (2021). Facile Protocol for the Synthesis of 2-Amino-4H-Chromene Derivatives using Choline Chloride/Urea. Organic Preparations and Procedures International: Vol. 53, No. 1, pp. 34-41.

  （2021年）。使用氯化胆碱/尿素合成2-氨基-4H-Chromene衍生物的简便方案。国际有机制剂和程序：第 53，第1号，第34-41页。
• K2CO3/cyanuric acid catalyzed synthesis of 2-amino-4H-chromene derivatives in water
  作者：Reza Heydari、Ramin Shahraki、Mahshid Hossaini、Alireza Mansouri

  DOI：10.1007/s11164-017-2900-0

  日期：2017.8

  Abstract Three-component processes for the synthesis of 2-amino-4H-chromenes catalyzed by potassium carbonate/cyanuric acid in water as a safe solvent were developed. These reactions were performed at room temperature through one-pot reactions. The benefits of this research are short reaction time, excellent yield, clean reaction media, simple work-up and easy purification. Graphical Abstract

  摘要 建立了碳酸钾/氰尿酸为安全溶剂的三组分合成2-氨基-4H-色烯的方法。这些反应在室温下通过一锅法进行。这项研究的好处是反应时间短，产率高，反应介质干净，后处理简单和易于纯化。 图形概要
• ELAGAMEY, ABDEL GHANI A.;SAWLLIM, SALAH Z.;EL-TAWEEL, FATHY M. A.;ELNAGDI+, COLLECT. CZECHOSL. CHEM. COMMUN., 53,(1988) N 7, C. 1534-1538
  作者：ELAGAMEY, ABDEL GHANI A.、SAWLLIM, SALAH Z.、EL-TAWEEL, FATHY M. A.、ELNAGDI+

  DOI：——

  日期：——
• Design, synthesis and in vitro evaluation of antitubercular and antimicrobial activity of some novel pyranopyrimidines
  作者：Nimesh R. Kamdar、Dhaval D. Haveliwala、Prashant T. Mistry、Saurabh K. Patel

  DOI：10.1016/j.ejmech.2010.08.014

  日期：2010.11

  The clinical significance of pyran and pyrimidine condensed systems and the raise in problem of multidrug resistant bacterial pathogens has directed us to synthesize pyranopyrimidine derivatives via the reactions of the versatile, 2-amino-4-(4-methoxyphenyl)-4H-substitutedchromene-3-carbonitrile with the appropriate reagents. The newly synthesized compounds were characterized by IR, H-1 NMR,C-13 NMR, Mass spectra and Elemental analysis. The compounds were evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H(37)Rv [ATCC-27294] and antibacterial activity against Staphylococcus aureus [ATCC-25923] and Streptococcus pyogenes [MTCC-443] as Gram-positive, Escherichia coli [ATCC-25922] and Pseudomonas aeruginosa [MTCC-441] as Gram-negative bacterial strains and antifungal activity against Aspergillus niger [MTCC-282]. Several derivatives exhibited pronounced antitubercular and antimicrobial activities. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Elagamey, Abdel Ghani A.; Sawllim, Salah Z.; El-Taweel, Fathy M.A., Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 7, p. 1534 - 1538
  作者：Elagamey, Abdel Ghani A.、Sawllim, Salah Z.、El-Taweel, Fathy M.A.、Elnagdi, Mohamed H.

  DOI：——

  日期：——