4-(4-dimethylaminophenyl)-3,4-dihydro-2H-chromeno[4,3-d]pyrimidine-2,5(1H)-dione

• 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-(4-dimethylaminophenyl)-3,4-dihydro-2H-chromeno[4,3-d]pyrimidine-2,5(1H)-dione
• 英文别名: 4-(4-(dimethylamino)phenyl)-3,4-dihydro-1H-chromeno[4, 3-d]pyrimidine-2,5-dione；4-[4-(dimethylamino)phenyl]-3,4-dihydro-1H-chromeno[4,3-d]pyrimidine-2,5-dione
• 化学式: C₁₉H₁₇N₃O₃
• 分子量: 335.362
• InChiKey: RPRRPYZKMUJDOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 对二甲氨基苯甲醛 、 尿素 在 Ag⁽⁰⁾ nanoparticles immobilized on SBA-15/cyclodextrin nanosponge adduct 作用下， 以 水 为溶剂， 反应 0.42h， 以90%的产率得到4-(4-dimethylaminophenyl)-3,4-dihydro-2H-chromeno[4,3-d]pyrimidine-2,5(1H)-dione
  参考文献：
  名称：

  固定在SBA-15 /环糊精纳米海绵加合物上的生物辅助合成Ag（0）纳米颗粒：超声辅助合成苯并吡喃并嘧啶类化合物的高效多相催化剂

  摘要：

  首次通过Cl官能化的SBA-15与胺官能化的环糊精纳米海绵（CDNS）的反应合成了SBA-15 /环糊精纳米海绵加合物。该加合物得益于SBA-15和CDNS的功能，然后被用于固定Ag（0）纳米颗粒，这些纳米颗粒是使用生物基方法制备和封端的。Ag @ CDNS–SBA-15被用作非均相催化剂，用于在超声辐射下促进苯甲醛，4-羟基香豆素和尿素或硫脲的三组分反应，以提供苯并吡喃并嘧啶。反应变量使用响应面方法进行了优化。Ag @ CDNS–SBA-15的催化活性高于Ag @ CDNS，Ag @ SBA-15和Ag @ SBA-15 + CDNS，确认这两种成分对催化的贡献以及CDNS和SBA-15之间的协同作用。CDNS的作用是容纳基质并将其带到Ag（0）纳米颗粒附近。值得注意的是，该催化剂是可重复使用的，并且可以回收利用，最多可重复使用四个反应，轻微的Ag（0）浸出并失去催化活性。

  DOI：

  10.1002/aoc.4286

文献信息

• One-pot facile and mild construction of densely functionalized pyrimidines in water <i>via</i> consecutive C–C and C–S bonds formation
  作者：Pramod K. Sahu、Praveen K. Sahu、Manvendra S. Kaurav、Mouslim Messali、Saud M. Almutairi、Puran L. Sahu、Dau D. Agarwal

  DOI：10.1039/c8ra04363a

  日期：——

  Fused pyrimidines composed of alternating heteroatoms and a pyrimidine moiety were synthesized efficiently using readily available starting material 4-hydroxycoumarin, aromatic aldehydes, and urea/thiourea at room temperature.

  利用现成的起始材料 4-羟基香豆素、芳香醛和脲/硫脲，在室温下高效合成了由交替杂原子和嘧啶分子组成的融合嘧啶。
• Rapid and mild synthesis of quinazolinones and chromeno[ d ]pyrimidinones using nanocrystalline copper(I) iodide under solvent-free conditions
  作者：Shahrzad Abdolmohammadi、Samira Karimpour

  DOI：10.1016/j.cclet.2015.08.014

  日期：2016.1

  very simple, efficient synthesis of quinazolinones and chromeno[ d ]pyrimidinones from the reaction of aryl aldehydes, urea/thiourea and active methylene compounds (dimedone/4-hydroxycoumarin) using nano-sized CuI particles under solvent-free conditions. The highlights of this new method are based on using an effective and recyclable catalyst, affording high yields of products, mild reaction conditions

  摘要本文描述了一种纳米级的CuI颗粒，在无溶剂条件下，由芳基醛，脲/硫脲与活性亚甲基化合物（二甲酮/ 4-羟基香豆素）反应，可非常简单，有效地合成喹唑啉酮和色胺并嘧啶酮。该新方法的亮点是基于使用有效且可回收的催化剂，可提供高收率的产品，温和的反应条件，简便的后处理和纯化方法。
• Bio-assisted synthesized Ag(0) nanoparticles immobilized on SBA-15/cyclodextrin nanosponge adduct: Efficient heterogeneous catalyst for the ultrasonic-assisted synthesis of benzopyranopyrimidines
  作者：Samahe Sadjadi、Majid M. Heravi、Masoumeh Malmir

  DOI：10.1002/aoc.4286

  日期：2018.4

  SBA‐15/cyclodextrin nanosponge adduct was synthesized through reaction of Cl‐functionalized SBA‐15 and amine‐functionalized cyclodextrin nanosponge (CDNS). This adduct, which benefits from features of both SBA‐15 and CDNS, was then used for immobilization of Ag(0) nanoparticles which were prepared and capped using a bio‐based approach. Ag@CDNS–SBA‐15 was applied as a heterogeneous catalyst for promoting

  首次通过Cl官能化的SBA-15与胺官能化的环糊精纳米海绵（CDNS）的反应合成了SBA-15 /环糊精纳米海绵加合物。该加合物得益于SBA-15和CDNS的功能，然后被用于固定Ag（0）纳米颗粒，这些纳米颗粒是使用生物基方法制备和封端的。Ag @ CDNS–SBA-15被用作非均相催化剂，用于在超声辐射下促进苯甲醛，4-羟基香豆素和尿素或硫脲的三组分反应，以提供苯并吡喃并嘧啶。反应变量使用响应面方法进行了优化。Ag @ CDNS–SBA-15的催化活性高于Ag @ CDNS，Ag @ SBA-15和Ag @ SBA-15 + CDNS，确认这两种成分对催化的贡献以及CDNS和SBA-15之间的协同作用。CDNS的作用是容纳基质并将其带到Ag（0）纳米颗粒附近。值得注意的是，该催化剂是可重复使用的，并且可以回收利用，最多可重复使用四个反应，轻微的Ag（0）浸出并失去催化活性。
• A Facile and Efficient Tamarind Juice Catalyzed One-Pot Synthesis of Benzopyranopyrimidines in Aqueous Medium Just by Grinding: A Green Chemistry Approach
  作者：Y. I. Shaikh、S. S. Shaikh、Khursheed Ahmed、G. M. Nazeruddin、V. S. Shaikh

  DOI：10.13005/ojc/360308

  日期：2020.6.30

  A comprehensive and efficient Tamarind (Tamarindous indica) juice catalysed one pot synthesis of benzopyranopyrimidines in aqueous medium through condensation of 4-Hydroxycoumarin (10mmol), various substituted benzaldehydes (10mmol)) and urea/thiourea (20mmol) just by grinding at ambient condition is reported in excellent yield of the product. This is a green chemistry approach, which is need of the hour.
• AN EFFICIENT SYNTHESIS OF BENZOPYRANOPYRIMIDINES USING INORGANIC SOLID SUPPORT
  作者：Mazaahir Kidwai、Pooja Sapra

  DOI：10.1081/scc-120004253

  日期：2002.1

  4-Hydroxycoumarin on reaction with aldehydes in the presence of urea/thiourea using solid inorganic support under microwave irradiation (MWI) afforded 4-substituted benzopyrano [4,3-d]- pyrimidine derivatives in a few seconds with improved yield as compared to conventional heating. This efficient, facile and ecofriendly technique avoids the use of excess solvent and toxic acids usually employed in the process.