12-(2-hydroxyphenyl)-8,10-dimethyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-dione | 1234482-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 12-(2-hydroxyphenyl)-8,10-dimethyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-dione
• 英文别名: 12‐(2‐hydroxyphenyl)‐8,12‐dihydro‐8,10‐dimethyl‐9H-naphtha[1',2':5,6]pyrano[2,3‐d]pyrimidine‐9,11‐(10H)‐dione；12-(2-hydroxyphenyl)-8,10-dimethyl-8,10-dihydro-9H-benzo[5,6]chromene[2,3,d]pyrimidine-9,11-(10H)-dione
• CAS: 1234482-01-9
• 化学式: C₂₃H₁₈N₂O₄
• 分子量: 386.407
• InChiKey: RFBAMYDKMLUNNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  73.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1,3-二甲基-6-氨基脲嘧啶 、 水杨醛 、 2-萘酚 在 氯化胆碱 、 氯乙酸 作用下， 以86 %的产率得到12-(2-hydroxyphenyl)-8,10-dimethyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-dione
  参考文献：
  名称：

  释放萘并吡喃并嘧啶的抗癌潜力：低共熔溶剂 (DES) 研究

  摘要：

  芳香醛、β-萘酚和 6-氨基-1,3-二甲基尿嘧啶在低共熔溶剂 (DES) 中的新型一锅三组分偶联 (3-CCR) 反应已被开发为一种高度共熔溶剂。一种高效、选择性的方法，用于快速合成密集功能化的8,10-二甲基-12-苯基-8,12-二氢-9 H-苯并[5,6]色并[2,3- d ]嘧啶-9,11 (10 H )-二酮骨架的合成产率令人满意。设计的方案巧妙地利用了 DES 的多功能性，从而产生了一种简单、经济高效、有弹性且环境可持续的合成方法。所得级联加合物对多种癌细胞系表现出显着的抗增殖活性，从而有望成为乳腺癌和肝细胞癌的潜在抗癌候选药物，具有中等至良好的 IC 50值。合成文库中最有效的化合物4m和4l对 HepG2 和 MCF7 癌细胞系表现出高效的细胞毒性，显着的 IC 50值分别为 46.39 和 28.21 μM。目前的发现得到了计算和分子对接研究的证实。密度泛函理论 (DFT)

  DOI：

  10.1039/d4nj00796d

文献信息

• Immobilization of Lewis acidic ionic liquid on perlite nanoparticle surfaces as a highly efficient solid acid catalyst for the solvent-free synthesis of xanthene derivatives
  作者：L. Moradi、M. Mirzaei

  DOI：10.1039/c9ra03312b

  日期：——

  modified with Lewis acidic ionic liquid (perlite NP@IL/ZrCl4) through a two step procedure. The prepared solid acid catalyst was characterized by Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX) and thermo gravimetric analysis (TGA). Perlite NP@IL/ZrCl4 was used as a new solid acid, reusable and green

  在这项研究中，珍珠岩纳米粒子通过简单的方法制备，然后通过两步过程用路易斯酸性离子液体（珍珠岩 NP@IL/ZrCl 4 ）进行改性。采用傅里叶变换红外光谱(FTIR)、扫描电子显微镜(SEM)、X射线衍射(XRD)、能量色散X射线光谱(EDX)和热重分析(TGA)对制备的固体酸催化剂进行了表征。珍珠岩 NP@IL/ZrCl 4被用作一种新的固体酸、可重复使用的绿色非均相纳米催化剂，用于一锅法合成呫吨衍生物。使用催化量（0.005 g，0.4 mol%）制备的催化剂在无溶剂条件下合成呫吨，后处理简单，产物收率高至优异。该催化剂的可重复使用性和高效率使该方法对大规模环保操作具有吸引力。
• MWCNTs@NHBut/PTA: New efficient solid acid catalyst for solvent free synthesis of benzochromenopyrimidines
  作者：Masoumeh Ahmadi、Leila Moradi、Masoud Sadeghzadeh

  DOI：10.1002/aoc.4980

  日期：2019.8

  In this study, a novel and eco‐friendly synthesis of benzochromenopyrimidines catalyzed by phosphotugstic acid immobilized on aminated multiwalled carbon nanotubes (MWCNTs@NHBut/PTA) is reported. New solid acid catalyst was prepared through a simple process with good percentage of organo metallic groups and characterized with FTIR, TEM, SEM, EDX and TGA techniques. Reusable catalytic system provides

  在这项研究中，报道了一种新型且环保的苯甲酰氨基嘧啶的合成方法，该方法由固定在胺化的多壁碳纳米管上的磷酸三氟乙酸催化（MWCNTs @ NHBut / PTA）。通过简单的方法制备了具有较高有机金属基团比例的新型固体酸催化剂，并通过FTIR，TEM，SEM，EDX和TGA技术对其进行了表征。可重复使用的催化系统提供了一种方便，安全和绿色的途径，可以在温和的条件下生成各种苯并铬嘧啶。
• First InCl3-Catalyzed, Three-Component Coupling of Aldehydes, β-Naphthol, and 6-Amino-1,3-dimethyluracil to Functionalized Naphthopyranopyrimidines
  作者：M. Singh、Ganesh Nandi、Subhasis Samai

  DOI：10.1055/s-0029-1219574

  日期：2010.4

  Indium(III) chloride was found to be a highly effective and efficient catalyst for the three-component, one-pot coupling of aldehydes, β-naphthol, and 6-amino-1,3-dimethyluracil under solvent-free conditions to give 8,10-dimethyl-12-aryl-12H-naphtho[1′,2′:5,6]pyrano[2,3-d]pyrimidine-9,11-diones in high yields for the first time. No co-catalyst or activator is required. Water and ammonia are the only byproducts in the reactions.

  铟(III)氯化物被发现是一种高效且有效的催化剂，能够在无溶剂条件下实现醛、β-萘酚和6-氨基-1,3-二甲基尿嘧啶的三组分、一锅反应的偶联，首次高产率地合成8,10-二甲基-12-芳基-12H-萘[1′,2′:5,6]吡喃[2,3-d]嘧啶-9,11-二酮。反应中不需要任何共催化剂或活化剂。水和氨是反应中的唯一副产物。
• 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.