9-(4-hydroxy-2-oxo-2H-chromen-3-yl)-3,3-dimethyl-7-nitro-2,3,4,9-tetrahydro-1H-xanthen-1-one | 1441018-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-(4-hydroxy-2-oxo-2H-chromen-3-yl)-3,3-dimethyl-7-nitro-2,3,4,9-tetrahydro-1H-xanthen-1-one
• 英文别名: 3,4-dihydro-9-(4-hydroxy-2-oxo-2H-chromen-3-yl)-3,3-dimethyl-7-nitro-2H-xanthen-1(9H)-one；9-(4-hydroxy-2-oxochromen-3-yl)-3,3-dimethyl-7-nitro-4,9-dihydro-2H-xanthen-1-one
• CAS: 1441018-85-4
• 化学式: C₂₄H₁₉NO₇
• 分子量: 433.417
• InChiKey: WTBRDTMDCASLQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 5,5-二甲基-1,3-环己二酮 、 5-硝基水杨醛 在 ONa on C coated Fe₃O₄ nanoparticles 作用下， 以 水 为溶剂， 反应 0.92h， 以88%的产率得到9-(4-hydroxy-2-oxo-2H-chromen-3-yl)-3,3-dimethyl-7-nitro-2,3,4,9-tetrahydro-1H-xanthen-1-one
  参考文献：
  名称：

  利用磁性纳米粒子催化剂绿色合成功能化4H-色烯的实验和理论机理研究的新见解

  摘要：

  使用Fe 3 O 4 @CONa纳米粒子在水中通过水杨醛（1），活性亚甲基（2）和碳基亲核试剂（3）的一锅，三组分反应进行绿色合成功能化4 H-色烯。在60°C下进行。铁3 O 4作为一种有效，绿色和可磁重复使用的多相催化剂，CONa纳米颗粒被用于这些反应中，直到九次运行。发现绿色催化剂和溶剂，较短的反应时间，较高的产品收率以及简单的后处理程序是该方法的一些优点。密度泛函理论计算应用于一锅，三组分反应机理的全包感知。最多的反应是通过以下途径进行的：（a）2比1的亲核加成；（b）闭环，脱水；（c）3（2-萘酚，4-羟基香豆素）亲核取代为中间体。有时将机制突变为：（a）将3（吲哚，2-甲基吲哚）亲核加成1，脱水；（b）将2亲核加成；（c）闭环和脱水。前沿的分子轨道，NBO分析，反应物的分子静电势和中间体证实了该提议机制。理论研究可能有助于挑选合适的反应物。

  DOI：

  10.1002/jccs.201900554

文献信息

• New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4 <i>H</i> ‐chromenes using magnetic nanoparticle catalyst
  作者：Hassan Ghavidel、Behrooz Mirza、Somayeh Soleimani‐Amiri、Mohammadreza Manafi

  DOI：10.1002/jccs.201900554

  日期：2020.10

  A green synthesis of functionalized 4H‐chromenes using one‐pot, three‐component reaction of salicylaldehyde (1), active methylene (2), and carbon‐based nucleophile (3) using Fe3O4@CONa nanoparticles in water has been performed at 60°C. The Fe3O4@CONa nanoparticle as an efficient, green, and magnetically reusable heterogeneous catalyst was applied in these reactions up to the nine runs. Green catalyst

  使用Fe 3 O 4 @CONa纳米粒子在水中通过水杨醛（1），活性亚甲基（2）和碳基亲核试剂（3）的一锅，三组分反应进行绿色合成功能化4 H-色烯。在60°C下进行。铁3 O 4作为一种有效，绿色和可磁重复使用的多相催化剂，CONa纳米颗粒被用于这些反应中，直到九次运行。发现绿色催化剂和溶剂，较短的反应时间，较高的产品收率以及简单的后处理程序是该方法的一些优点。密度泛函理论计算应用于一锅，三组分反应机理的全包感知。最多的反应是通过以下途径进行的：（a）2比1的亲核加成；（b）闭环，脱水；（c）3（2-萘酚，4-羟基香豆素）亲核取代为中间体。有时将机制突变为：（a）将3（吲哚，2-甲基吲哚）亲核加成1，脱水；（b）将2亲核加成；（c）闭环和脱水。前沿的分子轨道，NBO分析，反应物的分子静电势和中间体证实了该提议机制。理论研究可能有助于挑选合适的反应物。
• Nanocrystalline and Reusable ZnO Catalyst for the Assembly of Densely Functionalized 4<i>H</i>-Chromenes in Aqueous Medium via One-Pot Three Component Reactions: A Greener “NOSE” Approach
  作者：Partha Pratim Ghosh、Asish R. Das

  DOI：10.1021/jo400763z

  日期：2013.6.21

  An ecofriendly, One-pot, three component ZnO nanoparticles-mediated synthesis of 4H-chromene in water under thermal condition has been described. The highly product-selective three component electrophilic reaction of 2-hydroxybenzaldehyde with an active methylene compound and another carbon-based varied nature of nucleophile has been developed by a reversible alkylation procedure using greener "NOSE" approach. Greenness of the process was well instituted, as water was used both;as reaction media as well as medium for the synthesis of catalyst. In these reactions, the use of nano-ZnO as a catalyst was documented to be crucial for rendering the reactions possible in water media, while replacing nano-ZnO with other acids or bases resulted in the generation of too many side products. The catalyst can be efficiently recycled up to the sixth run, an essential point in the area of green chemistry. The methodology provides cleaner conversion, shorter reaction times, and high selectivity, which make the protocol globally putative. The crystal structures of 4H-chromene, easily produced by a chromatography-free highly product-selective reaction, were explored by means of single crystal X-ray diffraction analysis, and H-bonding arrangements of one signified compound prepared is presented. In optimized mild conditions, the isolated yields are 86-93%.
• Synthesis and molecular docking studies of oxochromenyl xanthenone and indolyl xanthenone derivatives as anti-HIV-1 RT inhibitors
  作者：Hanmant M. Kasralikar、Suresh C. Jadhavar、Sudhakar R. Bhusare

  DOI：10.1016/j.bmcl.2015.07.050

  日期：2015.9

  A series of novel oxochromenyl xanthenone and indolyl xanthenone derivatives were obtained by one-pot reaction of substituted salicylaldehyde, 4-hydroxy coumarin/indole and dimedone at ambient temperature condition using eco-friendly reusable ionic liquid [Hmim] HSO4 in ethanol solvent. Excellent yields, mild reaction condition, and simple experimental work-up procedure are some of the advantages of this method. The obtained derivatives were studied for their molecular docking as an anti-HIV-1 RT. All synthesized compounds from indolyl xanthenone and chromenyl xanthenone series were be docked into the non-nucleoside inhibitor binding pocket (NNIBP) of HIV-1 RT. Compounds 4r, 4j and 4k was found to be good around -12.487, -12.457, -12.256, respectively, with respective to native ligand TMC278, was found to be -13.413 which confirms that these compounds might have potent RT inhibition activity. (C) 2015 Elsevier Ltd. All rights reserved.
• Application of potassium-modified carbon nitride as a highly efficient recyclable catalyst for synthesis of 4H-chromene derivatives
  作者：Yu-Xuan Chen、Jia-Qi Di、Shan-Shan Geng、Zhan-Hui Zhang

  DOI：10.1007/s11164-021-04566-9

  日期：2022.1

  electron microscope (SEM), transmission electron microscope (TEM) and X-ray photoelectron spectroscopy (XPS) techniques. The obtained K-CN exhibited excellent catalytic activity for synthesis of 4 H -chromene derivatives via one-pot three-component reaction of salicylaldehyde, cyclohexane-1,3-diones and 4-hydroxycoumarin in water/ethyl lactate at room temperature. The reported method shows significant

  采用简单的热聚合法制备了钾掺杂氮化碳（K-CN）。采用傅里叶红外光谱(FT-IR)、粉末X射线衍射(XRD)、扫描电子显微镜(SEM)、透射电子显微镜(TEM)和X射线光电子能谱(XPS)技术对制备的K-CN进行表征。所得K-CN对水杨醛、环己烷-1,3-二酮和4-羟基香豆素在室温下在水/乳酸乙酯中的一锅三组分反应合成4 H-色烯衍生物具有优异的催化活性。该方法具有产率高、反应条件温和清洁、使用可回收催化剂和乳酸乙酯/水作为环保溶剂、室温下多组分反应等显着优点，