4,5-dihydro-5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,10H)-dione | 1441019-03-9

• 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: 4,5-dihydro-5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,10H)-dione
• 英文别名: 5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,5H)-dione；5-(4-hydroxy-2-oxochromen-3-yl)-1,3-dimethyl-5H-chromeno[2,3-d]pyrimidine-2,4-dione
• CAS: 1441019-03-9
• 化学式: C₂₂H₁₆N₂O₆
• 分子量: 404.379
• InChiKey: LUKYBWUVDNDYKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-二甲基-6-氨基脲嘧啶 、 水杨醛 在 氨基磺酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 4,5-dihydro-5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,10H)-dione
  参考文献：
  名称：

  合成 5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-1,3-二甲基-1H-chromeno[2,3-d]pyrimidine-2,4(3H, 5H)-二酮

  摘要：

  Nilam C. Dige、Prasad G. Mahajan、Ramdas K. Dhokale、Sarika M. Chinchkar、Mayuri V. Patil 和 Dattaprasad M. Pore 化学系，Shivaji 大学，科尔哈布尔，马哈拉施特拉邦，印度 416004 化学系，自然学院Science, Kongju National University, 56 Gongju Daehak-ro, Gongju 32588, Chungnam-do, Korea 艺术、科学和商业学院，Naldurg, Maharashtra, India 413602

  DOI：

  10.1080/00304948.2019.1677449

文献信息

• One-pot Three-component Route for the Synthesis of Functionalized 4<i>H</i>-chromenes Catalyzed by ZrOCl₂·8H₂O in Water
  作者：Azim Ziyaei Halimehjani、Nahid Keshavarzi

  DOI：10.1002/jhet.3081

  日期：2018.2

  method for the synthesis of functionalized 4H‐chromenes via a one‐pot three‐component condensation reaction of a 2‐hydroxybenzaldehyde with an active methylene compound and a carbon‐based nucleophile in the presence of a catalytic amount of ZrOCl2·8H2O in water under thermal condition has been described. High yields, simple work‐up procedure, performing reactions in water and synthesis of complex molecules

  在催化量的ZrOCl 2 ·8H存在下，通过2-羟基苯甲醛与活性亚甲基化合物和碳基亲核试剂的单锅三组分缩合反应合成官能化4 H色烯的有效方法2在热条件下的水ö已经描述。该方法的主要优点是高收率，简单的后处理程序，在水中进行反应以及通过一锅法进行复杂分子的合成。此外，X射线晶体学证实了水杨醛，2-萘酚和二甲酮缩合的产物结构。
• 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。
• An efficient method for the synthesis of functionalized 4H-chromenes as optical sensor for detection of Fe3+ in ethanol
  作者：Zohreh Kheilkordi、Ghodsi Mohammadi Ziarani、Negar Lashgari、Alireza Badiei

  DOI：10.1016/j.poly.2019.03.042

  日期：2019.7

  An efficient method for the synthesis of functionalized 4H-chromenes via a one-pot three-component condensation reaction of a 2-hydroxybenzaldehyde with an active methylene compound and a carbon-based nucleophile in the presence of SrFe12O19 as catalyst under solvent-free at 80 degrees C condition has been described. SrFe12O19 was an efficient, green, and reusable magnetic nanoparticles as heterogeneous catalyst with the average particles size of 70 nm which can be recycled and readily separated from the reaction mixture using an external magnet. High product yields, simple work-up procedure, solvent-free conditions and characterization of the sensing properties of compound 4a for detection of Fe3+ ion are the main advantages of this procedure. The sensing ability of compound 4a was examined upon addition of a wide variety of cations both visually and by UV-Vis spectroscopy. The increase in UV-Vis absorbance was linearly proportional to the concentration of Fe3+ with a detection limit of 1.0 x 10(-7) M. Moreover, the chemosensor exhibited an obvious color change from white to yellow in the presence of Fe3+ in EtOH solution. (C) 2019 Elsevier Ltd. All rights reserved.
• 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%.
• Novel Route for the Synthesis of 5-(4-Hydroxy-2-oxo-2<i>H</i>-chromen-3-yl)-1,3-dimethyl-1<i>H</i>-chromeno[2,3-<i>d</i>]pyrimidine-2,4(3<i>H</i>,5<i>H</i>)-diones
  作者：Nilam C. Dige、Prasad G. Mahajan、Ramdas K. Dhokale、Sarika M. Chinchkar、Mayuri V. Patil、Dattaprasad M. Pore

  DOI：10.1080/00304948.2019.1677449

  日期：2019.11.2

  Nilam C. Dige, Prasad G. Mahajan, Ramdas K. Dhokale, Sarika M. Chinchkar, Mayuri V. Patil, and Dattaprasad M. Pore Department of Chemistry, Shivaji University, Kolhapur, Maharashtra, India 416004 Department of Chemistry, College of Natural Science, Kongju National University, 56 Gongju Daehak-ro, Gongju 32588, Chungnam-do, Republic of Korea Arts, Science and Commerce College, Naldurg, Maharashtra,

  Nilam C. Dige、Prasad G. Mahajan、Ramdas K. Dhokale、Sarika M. Chinchkar、Mayuri V. Patil 和 Dattaprasad M. Pore 化学系，Shivaji 大学，科尔哈布尔，马哈拉施特拉邦，印度 416004 化学系，自然学院Science, Kongju National University, 56 Gongju Daehak-ro, Gongju 32588, Chungnam-do, Korea 艺术、科学和商业学院，Naldurg, Maharashtra, India 413602