12-(4-bromophenyl)-8,10-dimethyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-dione | 1187642-18-7

• 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-(4-bromophenyl)-8,10-dimethyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-dione
• 英文别名: 18-(4-Bromophenyl)-13,15-dimethyl-11-oxa-13,15-diazatetracyclo[8.8.0.02,7.012,17]octadeca-1(10),2,4,6,8,12(17)-hexaene-14,16-dione；18-(4-bromophenyl)-13,15-dimethyl-11-oxa-13,15-diazatetracyclo[8.8.0.02,7.012,17]octadeca-1(10),2,4,6,8,12(17)-hexaene-14,16-dione
• CAS: 1187642-18-7
• 化学式: C₂₃H₁₇BrN₂O₃
• 分子量: 449.304
• InChiKey: ZCUFGYQFGYZOKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 、 对溴苯甲醛 、 2-萘酚 在 1,10-(6-(propyl amino)-1,3,5-triazine-2,4-diyl)bis(pyridinium)hydrogen sulfate immobillized on functionalized halloysite nanotubes 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 以97%的产率得到12-(4-bromophenyl)-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：

  固定在功能化埃洛石纳米管上的三嗪双（吡啶鎓）硫酸氢盐离子液体作为一锅法合成萘并吡喃嘧啶的有效催化剂

  摘要：

  1,1'-(6-(丙基氨基)-1,3,5-triazine-2,4-diyl)bis(pyridinium)硫酸氢盐固定在埃洛石纳米管[(PATDBP)(HSO 4 ) 2 @HNT]上通过FT-IR、TGA、SEM/EDX、元素映射、TEM和元素分析等多种分析技术成功合成并表征了固体酸纳米催化剂。发现该催化剂在无溶剂条件下通过 β-萘酚、醛类和N , N-二甲基巴比妥酸的一锅三组分反应以优异的产率方便地合成萘并吡喃并嘧啶衍生物。此外，该催化剂可以回收和重复使用五次，而不会显着降低其活性。

  DOI：

  10.1039/d1ra01230d

文献信息

• Phosphoric acid supported on alumina (H3PO4/Al2O3) as an efficient and reusable catalyst for the one-pot synthesis of benzoxanthene pigments
  作者：Hamid Reza Shaterian、Kobra Azizi、Nafiseh Fahimi

  DOI：10.1007/s11164-013-1047-x

  日期：2014.4

  Phosphoric acid supported on alumina (H3PO4/Al2O3) is an efficient catalyst for the catalytic multi-component condensation reaction and a wide variety of syntheses of benzoxanthene pigments in good yields. The remarkable features of this new procedure are high conversions, shorter reaction times, cleaner reaction, and simple experimental and work-up procedures.

  负载于氧化铝上的磷酸（H3PO4/Al2O3）是一种高效的催化剂，可用于催化多组分缩合反应及一系列在良好产率下合成苯并二氧杂蒽类色素的合成中。该新方法的显著特点包括高转化率、较短的反应时间、更纯净的反应过程及简单易行的实验和后处理步骤。
• An efficient one-pot synthesis of tetrahydrobenzo[a]xanthene-11-one and diazabenzo[a]anthracene-9,11-dione derivatives under solvent free condition
  作者：Ganesh Chandra Nandi、Subhasis Samai、Ram Kumar、M.S. Singh

  DOI：10.1016/j.tet.2009.06.024

  日期：2009.8

  Indium(III) chloride catalyzed one-pot synthesis of 12-aryl/alkyl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one and 8,10-dimethyl-12-aryl-8,12-dihydro-7-oxa-8,10-diazabenzo[a]anthracene-9,11-dione derivatives have been achieved by three component cyclocondensation of aldehydes, β-naphthol and cyclic 1,3-dicarbonyl compounds under solvent free condition in high yields. P2O5 too has been found as an effective

  氯化铟（III）催化一锅合成12-芳基/烷基-8,9,10,12-四氢苯并[ a ]氧杂蒽-11-one和8,10-二甲基-12-芳基-8,12-二氢通过醛，β-萘酚和环状1,3-二羰基化合物在无溶剂条件下的三组分环缩合，可以高产率获得-7-氧杂-8,10-二氮杂苯并[ a ]蒽-9,11-二酮衍生物。还发现P 2 O 5是实现该转化的有效催化剂。
• ZrOCl2/nano TiO2 as an Efficient Catalyst for the One Pot Synthesis of Naphthopyranopyrimidines Under Solvent-free Conditions
  作者：Mahboubeh Mohaqeq、Javad Safaei-Ghomi、Hossein Shahbazi-Alavi

  DOI：10.17344/acsi.2015.1567

  日期：2015.12.15

  ZrOCl(2)/nano-TiO(2) has been used as an efficient catalyst for the preparation of naphtho[1',2':5,6]pyrano[2,3-d]pyrimidine derivatives by the three-component reaction of aldehydes, β-naphthol and 1,3-dimethylbarbituric acid. The advantages of the reaction are solvent-free conditions, short reaction times, easy workup, good to excellent yields, and cost-effective and reusable catalyst.

  ZrOCl（2）/ nano-TiO（2）已被用作通过三组分反应制备萘并[1'，2'：5,6]吡喃并[2,3-d]嘧啶衍生物的有效催化剂醛，β-萘酚和1,3-二甲基巴比妥酸 该反应的优点是无溶剂条件，反应时间短，后处理容易，收率好至极好，以及具有成本效益和可重复使用的催化剂。
• Synthesis and Biological Evaluation of Naphthopyranopyrimidines Derivatives as Potential Antifungal and Antibacterial Activities
  作者：Ramakoteswara Rao Chinta、V. Harikrishna、Vijaya Kumar Tulam、Prathama S. Mainkar、P.K. Dubey

  DOI：10.14233/ajchem.2016.19546

  日期：——

  A new series of novel 8,10-dimethyl-12-aryl-12H-naphtho[1,2,5,6]pyrano[2,3-d]pyrimidine-9,11-diones derivatives synthesized from coupling (3CC) of aldehydes, b-naphthol and 1,3-dimethylbarbituric acid derivatives with using green condition through a simple, mild and efficient procedure utilizing cellulose sulfuric acid as a catalyst. Final compounds were evaluated for antibacterial and antifungal activity. Compounds 4a, 4d, 4h display high potent antifungal activity against Candida parapsilopsis, compound 4d show more potent activity (MIC 4.6 mg/mL) better than miconazole. While compound 4d most effective on bacterial against Micrococcus luteus, Staphylococcus aureus MTCC 96 and Staphylococcus aureus MTCC 2940 with (MIC 2.3 mg/mL).

  以纤维素硫酸为催化剂，通过简单、温和、高效的程序，利用醛、b-萘酚和 1,3-二甲基巴比妥酸衍生物的偶联（3CC），在绿色条件下合成了一系列新型 8,10-二甲基-12-芳基-12H-萘并[1,2,5,6]吡喃并[2,3-d]嘧啶-9,11-二酮衍生物。对最终化合物进行了抗菌和抗真菌活性评估。化合物 4a、4d 和 4h 对拟白色念珠菌具有很强的抗真菌活性，其中化合物 4d 的活性（MIC 4.6 mg/mL）优于咪康唑。化合物 4d 对黄体微球菌、金黄色葡萄球菌 MTCC 96 和金黄色葡萄球菌 MTCC 2940 的细菌活性最强（MIC 为 2.3 毫克/毫升）。
• Iodine-catalyzed three-component one-pot synthesis of naphthopyranopyrimidines under solvent-free conditions
  作者：K. Praveen Kumar、S. Satyanarayana、P. Lakshmi Reddy、G. Narasimhulu、Narender Ravirala、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2012.01.096

  日期：2012.4

  Iodine is found to be a highly efficient catalyst for the three-component coupling (3CC) of aldehydes, β-naphthol, and 1,3-dimethylbarbituric acid under solvent-free conditions to afford the corresponding 8,10-dimethyl-12-aryl-12H-naphtho[1′,2′5,6]pyrano[2,3-d]pyrimidine-9,11-diones in good yields with high selectivity. The use of readily available iodine makes this method very simple, convenient,

  发现碘是无溶剂条件下醛，β-萘酚和1,3-二甲基巴比妥酸的三组分偶联（3CC）的高效催化剂，可提供相应的8,10-二甲基-12-芳基-12 H-萘并[1'，2'5,6]吡喃并[2,3 - d ]嘧啶-9,11-二酮的收率高，选择性高。使用现成的碘使这种方法非常简单，方便且具有成本效益。