1-(3-chlorophenyl)-3-methylchromeno[4,3-c]pyrazol-4(1H)-one | 110613-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3-chlorophenyl)-3-methylchromeno[4,3-c]pyrazol-4(1H)-one
• 英文别名: 1-(3-Chlorophenyl)-3-methylchromeno[4,3-c]pyrazol-4-one
• CAS: 110613-13-3
• 化学式: C₁₇H₁₁ClN₂O₂
• 分子量: 310.74
• InChiKey: CFTBMTBRESYERO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氯苯肼盐酸盐 在 对甲苯磺酸 作用下， 以 乙醇 、 xylene 为溶剂， 生成 1-(3-chlorophenyl)-3-methylchromeno[4,3-c]pyrazol-4(1H)-one
  参考文献：
  名称：

  中心苯并二氮杂receptor受体配体1-芳基和2-芳基[1]苯并吡喃并唑-4-酮的合成，结合研究及构效关系。

  摘要：

  DOI：

  10.1021/jm00396a001

文献信息

• Copper-catalyzed Cyclization of 3-Acylcoumarin Hydrazone using Air as the Oxidant: Efficient Synthesis of Pyrazole-Fused Coumarin Derivatives
  作者：Hui-Yan Wang、Xue-Cheng Liu、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1002/jhet.2052

  日期：2015.3

  3‐c]pyrazol‐4(1H)‐ones is reported. In this atom economic process, readily available 3‐acylcoumarin hydrazone is oxidative cyclized by direct C–N bond formation. Air has been successfully used as an oxidant, which has important economic and environmental advantages. A broad scope of 3‐acylcoumarin hydrazones can be utilized in this process.

  据报道，高效，便捷的Cu催化形成了铬诺[4,3 - c ]吡唑-4（1 H）-酮。在这个原子经济过程中，容易获得的3酰基香豆素通过直接的C–N键形成而被氧化环化。空气已成功地用作氧化剂，具有重要的经济和环境优势。在此过程中，可以使用各种3-酰基香豆素。
• One-Pot Cascade Access to Ru(II)-Catalyzed Regioselective C(sp²)-H Activation/Alkenylation of Chromeno[4,3-<i>c</i>]pyrazol-4-ones and Their Emission Solvatochromic Studies
  作者：Dinesh Singla、Kamaldeep Paul

  DOI：10.1021/acs.joc.2c02130

  日期：2022.12.16

  Herein, one-pot cascade synthesis of chromeno[4,3-c]pyrazol-4-ones and their Ru(II)-catalyzed regioselective ortho-alkenylation using imine as a weak directing group are done with moderate to good yields. The reaction proceeds through a three-step domino process during which intermediates are also isolated in excellent yields. In addition, this methodology generates a number of interesting fluorophores

  在此，使用亚胺作为弱导向基团的一锅法级联合成 chromeno[4,3 - c ]pyrazol-4-ones 及其 Ru(II) 催化的区域选择性邻位烯基化反应具有中等至良好的收率。反应通过三步多米诺骨牌过程进行，在此过程中中间体也以优异的产率分离。此外，该方法还产生了许多具有供体和受体基团的有趣荧光团，这些荧光团显示出正溶剂化显色现象。
• Synthesis, anticancer activity and photophysical properties of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates
  作者：J. Ashok Kumar、G. Saidachary、G. Mallesham、B. Sridhar、Nishant Jain、Shashi Vardhan Kalivendi、V. Jayathirtha Rao、B. China Raju

  DOI：10.1016/j.ejmech.2013.03.042

  日期：2013.7

  2-Oxo-2H-chromenylpyrazolecarboxylates (8a-h and 12a-zb) have been synthesized by [3 + 2] cycloaddition of 2H-chromenophenylhydrazones (7a-h and 11a-w) with diethyl/dimethylbut-2-ynedioates. Phenylchromeno[4,3-c]pyrazol-4(1H)-ones (13i-n) were prepared from corresponding phenylhydrazones (7a-h) with catalytic amount of piperidine in presence of pyridine as a solvent at 100 degrees C. All the synthesized compounds (8a-h, 12a-zb and 13a-n) were screened for anticancer activity against three human cancer cell lines such as prostate (DU-145), lung adenocarcinoma (A549), and cervical (HeLa) by standard MTT assay method. Further, photophysical properties (UV and fluorescence) for these compounds were discussed. (C) 2013 Elsevier Masson SAS. All rights reserved.