4-(3-nitrophenyl)-3,4-dihydro-1H-chromeno[4,3-d]pyrimidine-2,5-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-(3-nitrophenyl)-3,4-dihydro-1H-chromeno[4,3-d]pyrimidine-2,5-dione
• 化学式: C₁₇H₁₁N₃O₅
• 分子量: 337.291
• InChiKey: HWDDSUUCKWYZNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 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：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 间硝基苯甲醛 、 尿素 在 sodium dodecyl-sulfate 作用下， 以 水 为溶剂， 生成 4-(3-nitrophenyl)-3,4-dihydro-1H-chromeno[4,3-d]pyrimidine-2,5-dione
  参考文献：
  名称：

  One-pot facile and mild construction of densely functionalized pyrimidines in water via consecutive C–C and C–S bonds formation

  摘要：

  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。

  DOI：

  10.1039/c8ra04363a

文献信息

• Heteropolyacid@creatin-halloysite clay: an environmentally friendly, reusable and heterogeneous catalyst for the synthesis of benzopyranopyrimidines
  作者：Samahe Sadjadi、Majid M. Heravi、Masoumeh Malmir

  DOI：10.1007/s11164-017-3016-2

  日期：2017.11

  A novel hybrid catalyst has been designed and synthesized based on the incorporation of heteropolyacid into creatin-functionalized halloysite clay. The catalyst was characterized by using SEM/EDS, FTIR, XRD, BET, ICP-AES, TGA and DTGA, and successfully applied for promoting the synthesis of two series of benzopyranopyrimidines under ultrasonic irradiation in aqueous media. The results established the efficiency of this protocol in terms of product yield, reaction time and the eco-friendly nature of the process. Moreover, immobilization of heteropolyacid on creatin-functionalized halloysite circumvents heteropolyacid leaching and rendered the catalyst highly reusable.

  一种新型复合催化剂已被设计和合成，该催化剂是基于将杂多酸引入功能化的肌酸膨润土泥土中。通过使用扫描电子显微镜/能谱仪（SEM/EDS）、傅里叶变换红外光谱（FTIR）、X射线衍射（XRD）、比表面积测定（BET）、电感耦合等离子体原子发射光谱（ICP-AES）、热重分析（TGA）和微分热分析（DTGA）对催化剂进行了表征，并成功应用于促进在水相介质中超声照射下合成两系列苯并吡喃嘧啶。结果证明该方法在产物产率、反应时间和环保性方面的高效性。此外，杂多酸在功能化的肌酸膨润土上的固定化避免了杂多酸的浸出，使得催化剂具有较高的重复使用性。
• Tannic Acid Catalyzed Green Synthesis of Functionalized Chromeno-Pyrimidine-2,5-dione/thione Derivatives
  作者：J. Puvithra、D. Parthiban

  DOI：10.14233/ajchem.2020.22771

  日期：——

  Diversely functionalized chromeno-pyrimidine-2,5-dione/thione compounds were synthesized by cyclocondensation of 4-hydroxy coumarin, aldehydes and urea/thiourea using tannic acid as a green catalyst and 1:1 (EtOH:H2O) as a green solvent. Different acids were screened for their catalytic activity of chromeno-pyrimidine-2,5-dione/thione derivatives. Tannic acid (10 mol%) was used as a suitable catalyst with increased catalytic activity. By utilizing this protocol, chromeno-pyrimidine scaffolds were prepared in acceptable to excellent yield without the use of conventional volatile organic solvent and toxic metal catalyst. To our best of knowledge, this is the first report, in which tannic acid is utilized successfully as an eco-safe catalyst for synthesis of fused pyrimidines.

  使用丹宁酸作为绿色催化剂，以4-羟基香豆素、醛类和尿素/硫脲为原料，通过环缩合反应在1:1（乙醇:水）的绿色溶剂中合成了多样化官能团化的咖啡因-嘧啶-2,5-二酮/硫酮化合物。筛选了不同的酸类催化剂，发现10%丹宁酸具有较高的催化活性。使用该方法，可以在不使用传统挥发性有机溶剂和有毒金属催化剂的情况下，制备出可接受至优良的产率的咖啡因-嘧啶骨架。据我们所知，这是首次成功地利用丹宁酸作为环状嘧啶合成的生态安全催化剂的报告。
• 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。
• One-Pot Synthesis of Novel Heterocyclic Chromenopyrimidine-2,5-Dione and ThioxochromEnopyrimidin-5-one Derivatives
  作者：Hossein Mehrabi、Mohammad Baniasad-Dashtabi

  DOI：10.3184/174751915x14305809607197

  日期：2015.5

  Novel heterocyclic dihydropyrimidine chromenopyrimidine-2,5-diones and thioxochromenopyrimidin-5-ones were synthesised by a three-component reaction between 4-hydroxycoumarin, urea or thiourea, and aromatic aldehydes in H₂O under reflux in the presence of sodium dodecyl sulfate (20 mol%) and two drops of acetic acid. The products were obtained in good yields and their structures of all the synthesised compounds were established by spectroscopic methods..

  在十二烷基硫酸钠（20 mol%）和两滴乙酸的存在下，4-羟基香豆素、脲或硫脲和芳香醛在 H2O 回流条件下发生三组分反应，合成了新型杂环二氢嘧啶色嘧啶-2,5-二酮和硫酮色嘧啶-5-酮。所有合成化合物均以良好的收率获得，并通过光谱方法确定了它们的结构。
• A new Hg2+ colorimetric chemosensor: the synthesis of chromeno[d]pyrimidine-2,5-dione/thione derivatives using Fe3O4@SiO2@(BuSO3H)3
  作者：Negar Jamasbi、Ghodsi Mohammadi Ziarani、Fatemeh Mohajer、Alireza Badiei

  DOI：10.1007/s11164-021-04611-7

  日期：2022.2

  The synthesis of chromeno[ d ]pyrimidine-2,5-dione/thione derivatives has been described by the reaction of aryl aldehydes, urea/thiourea, and 4-hydroxycoumarin using Fe 3 O 4 @SiO 2 @(BuSO 3 H) 3 as catalyst under microwave irradiation (MWI) in H 2 O. The sensing application of 4-(4-chlorophenyl)-3,4-dihydro-1 H -chromeno[4,3- d ]pyrimidine-2,5-dione 4b was examined upon addition of different cations

  色烯[d]嘧啶-2,5-二酮/硫酮衍生物的合成已经通过芳基醛、脲/硫脲和4-羟基香豆素使用Fe 3 O 4 @SiO 2 @(BuSO 3 H) 3 的反应进行了描述在 H 2 O 中作为微波辐射 (MWI) 下的催化剂。 4-(4-chlorophenyl)-3,4-dihydro-1 H -chromeno[4,3-d]pyrimidine-2,5-dione 4b 的传感应用通过紫外-可见分光光度法在添加不同的阳离子后进行检测，并通过增加吸收对 Hg 2+ 离子表现出优异的灵敏度。紫外-可见吸收光谱数据显示，化学传感器 4b 的紫外-可见吸收与 Hg 2+ 浓度之间具有良好的线性关系，检测限为 3.76 × 10 -7 M。此外，化学传感器 4b 的颜色从白色变化明显在 EtOH 溶液中存在 Hg 2+ 时变为浅粉色。图形摘要