3,3'-((4-oxo-4H-chromen-3-yl)methylene)bis(4-hydroxy-2H-chromen-2-one) | 1313497-00-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3,3'-((4-oxo-4H-chromen-3-yl)methylene)bis(4-hydroxy-2H-chromen-2-one)
• 英文别名: 4-Hydroxy-3-[(4-hydroxy-2-oxo-chromen-3-yl)-(4-oxochromen-3-yl)methyl]chromen-2-one；4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)-(4-oxochromen-3-yl)methyl]chromen-2-one
• CAS: 1313497-00-5
• 化学式: C₂₈H₁₆O₈
• 分子量: 480.43
• InChiKey: YIEQGZHYLKMVQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  131.09
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  4-hydroxycoumarin 、 色酮-3-甲醛 在 (1S)-(+)-10-camphorsulfonic acid 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以73%的产率得到3,3'-((4-oxo-4H-chromen-3-yl)methylene)bis(4-hydroxy-2H-chromen-2-one)
  参考文献：
  名称：

  樟脑磺酸催化的合成3,3'-（芳基亚甲基）双（4-羟基-2H-铬-2-基），3,3'-（芳基亚甲基）双（2-羟基萘-1）的通用方法，4-二酮）和3,3'-（2-氧代吲哚啉-3,3-二基）双（2-羟基萘-1,4-二酮）衍生物在室温下

  摘要：

  摘要 已开发出樟脑磺酸催化的简单，有效且通用的方法，用于合成3,3'-（芳基亚甲基）双（4-羟基-2 H-铬烯-2-酮），3,3'-（芳基亚甲基））在室温下于室温下在乙醇水溶液中生成双（2-羟基萘-1,4-二酮）和3,3'-（2-氧代吲哚-3,3-二基）双（2-羟基萘-1,4-二酮）衍生物各种芳香醛与4-羟基香豆素或2-羟基萘-1,4-二酮的反应。温和的反应条件，使用无金属的有机催化剂，良好或优异的收率，高原子经济性，对环境无害，产物易于分离以及无需柱色谱分离是该开发方案的一些主要优点。

  DOI：

  10.1080/00397911.2020.1856877

文献信息

• Zwitterionic liquid (ZIL) coated CuO as an efficient catalyst for the green synthesis of bis-coumarin derivatives via one-pot multi-component reactions using mechanochemistry
  作者：Mayank Mayank、Amanpreet Singh、Pushap Raj、Randeep Kaur、Ajnesh Singh、Navneet Kaur、Narinder Singh

  DOI：10.1039/c6nj03763a

  日期：——

  convenient, solvent free strategy for the synthesis of bis-coumarins has been developed using zwitterionic liquid (ZIL) coated copper oxide (CuO) and mechanical ball milling. The ZIL were fabricated from imidazolium/benzimidazolium and sulfonate/carboxylate based moieties. Use of the ZIL offers an interesting multifunctional opportunity to immobilize them over CuO using the anionic part and the cationic part

  使用两性离子液体（ZIL）涂覆的氧化铜（CuO）和机械球磨，已经开发了一种方便，无溶剂的双香豆素合成策略。的ZIL从咪唑/苯并咪唑和磺酸/羧酸盐基于部分制造。ZIL的使用提供了一个有趣的多功能机会，可以使用阴离子部分将它们固定在CuO上，而阳离子部分则可以自由用于催化应用。使用扫描电子显微镜，透射电子显微镜，能量色散X射线光谱，粉末X射线衍射，循环伏安法，固态紫外可见吸收和光谱发射法对杂化催化剂进行了充分表征。他们三个发现生成的基于ZIL的和CuO偶联的杂化催化剂（ZIL @ CuO1-3）具有各种尺寸，形状，光物理特征和电化学性质。ZIL和CuO在ZIL @ CuO1中的超分子组装与其各自的母体组分以及其他两种杂化材料ZIL @ CuO2-3相比，催化活性大大提高。。通过改变所用球的数量，研磨时间和研磨速度来优化反应条件。使用质子-核磁光谱法阐明了反应机理，并使用光谱法充分鉴定了所有最终
• Synthesis of 4-Hydroxycoumarin Heteroarylhybrids as Potential Antimicrobial Agents
  作者：Zeba N. Siddiqui、Mohammed Musthafa T. N.、Anis Ahmad、Asad U. Khan

  DOI：10.1002/ardp.201000218

  日期：2011.6

  yields. The synthesized compounds were characterized on the basis of their elemental and spectral (IR, 1H‐NMR and mass spectrometry) analysis. All target compounds were evaluated for their in‐vitro antimicrobial activity against Streptococcus pyogenes, methicillin‐resistant Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumonia, and Escherichia coli bacterial strains and fungal cultures of

  通过3-溴-4-羟基香豆素1与各种杂醛2a-d反应合成了一系列新的4-羟基香豆素衍生物3a-d，收率良好。合成的化合物在元素和光谱（IR、1H-NMR 和质谱）分析的基础上进行了表征。所有目标化合物的体外抗菌活性均通过轻微扩散试验评估了对化脓性链球菌、耐甲氧西林金黄色葡萄球菌、铜绿假单胞菌、肺炎克雷伯菌、白色念珠菌、曲霉菌和毛癣菌的大肠杆菌菌株和真菌培养物的体外抗菌活性修改。测定了测试化合物以及参考标准的最小抑制浓度（MIC）。在测试的化合物中，
• Solvent- and catalyst-free synthesis of bis-adducts of 3-formylchromone as potential antimicrobial agents
  作者：Zeba N. Siddiqui、T. N. Mohammed Musthafa、Shagufta Praveen

  DOI：10.1007/s00044-012-0013-2

  日期：2013.1

  A facile and ecofriendly synthesis of new (chromon-3-yl)bis(heteroaryl)methanes 5a-d, from 3-formylchromone 1 and active methylene compounds 2-4 is reported under solvent-free, catalyst-free thermal heating condition in good yields. The synthesized compounds were characterized on the basis of elemental and spectral (IR, H-1 NMR, and mass spectrometry) analysis. All the target compounds were evaluated for their in vitro antimicrobial activity against Streptococcus pyogenes, Methicillin resistant Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumoniae, and Escherichia coli bacterial strains, and fungal cultures of Candida albicans, Aspergillus fumigatus, Trichophyton mentagrophytes, and Penicillium marneffei by disk diffusion assay with slight modifications. The minimum inhibitory concentration was determined for the test compounds as well as for reference standards. Among the tested compounds, 5b has shown the most potent antibacterial as well as antifungal activities.
• Camphor sulfonic acid catalyzed facile and general method for the synthesis of 3,3'-(arylmethylene)<i>bis</i>(4-hydroxy-2<i>H</i>-chromen-2-ones), 3,3'-(arylmethylene)<i>bis</i>(2-hydroxynaphthalene-1,4-diones) and 3,3'-(2-oxoindoline-3,3-diyl)<i>bis</i>(2-hydroxynaphthalene-1,4-dione) derivatives at room temperature
  作者：Gurpreet Kaur、Diksha Singh、Arvind Singh、Bubun Banerjee

  DOI：10.1080/00397911.2020.1856877

  日期：2021.4.3

  sulfonic acid catalyzed a straightforward, efficient, and general method has been developed for the synthesis of 3,3'-(arylmethylene)bis(4-hydroxy-2H-chromen-2-ones), 3,3'-(arylmethylene)bis(2-hydroxynaphthalene-1,4-diones) and 3,3'-(2-oxoindoline-3,3-diyl)bis(2-hydroxynaphthalene-1,4-dione) derivatives in aqueous ethanol at room temperature from the reactions of various aromatic aldehydes and 4-hydroxycoumarin

  摘要 已开发出樟脑磺酸催化的简单，有效且通用的方法，用于合成3,3'-（芳基亚甲基）双（4-羟基-2 H-铬烯-2-酮），3,3'-（芳基亚甲基））在室温下于室温下在乙醇水溶液中生成双（2-羟基萘-1,4-二酮）和3,3'-（2-氧代吲哚-3,3-二基）双（2-羟基萘-1,4-二酮）衍生物各种芳香醛与4-羟基香豆素或2-羟基萘-1,4-二酮的反应。温和的反应条件，使用无金属的有机催化剂，良好或优异的收率，高原子经济性，对环境无害，产物易于分离以及无需柱色谱分离是该开发方案的一些主要优点。