12-phenyl-8,12-dihydro-8,10-dimethyl-9H-naphtho[1',2':5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-dione | 1187642-13-2

• 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-phenyl-8,12-dihydro-8,10-dimethyl-9H-naphtho[1',2':5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-dione
• 英文别名: 8,10-dimethyl-12-phenyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-dione；13,15-Dimethyl-18-phenyl-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；13,15-dimethyl-18-phenyl-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: 1187642-13-2
• 化学式: C₂₃H₁₈N₂O₃
• 分子量: 370.408
• InChiKey: PPXYUUVWAIVPBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 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-6-氨基脲嘧啶 、 苯甲醛 、 2-萘酚 在 indium(III) chloride 作用下， 反应 0.42h， 以80%的产率得到12-phenyl-8,12-dihydro-8,10-dimethyl-9H-naphtho[1',2':5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-dione
  参考文献：
  名称：

  First InCl3-Catalyzed, Three-Component Coupling of Aldehydes, β-Naphthol, and 6-Amino-1,3-dimethyluracil to Functionalized Naphthopyranopyrimidines

  摘要：

  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。

  DOI：

  10.1055/s-0029-1219574

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。
• Molecular iodine-catalyzed one-pot synthesis of tetrahydrobenzo[a]xanthene-11-one and diazabenzo[a]anthracene-9,11-dione derivatives under microwave irradiation
  作者：X. J. Sun、J. F. Zhou、P. S. Zhao

  DOI：10.1002/jhet.742

  日期：2011.11

  An efficient one‐pot condensation of β‐naphthol, aldehydes, and cyclic 1,3‐dicarbonyl compounds has been achieved with molecular iodine as a catalyst under microwave irradiation, thus a variety of tetrahydrobenzo[a]xanthene‐11‐one and diazabenzo[a]anthracene‐9,11‐dione derivatives were prepared in good yields. J. Heterocyclic Chem., (2011).

  在微波辐射下，以分子碘为催化剂，可以实现β-萘酚，醛和环状1,3-二羰基化合物的高效单锅缩合反应，因此可以制得各种四氢苯并[ a ]蒽并十一酮和重氮苯并[以高收率制备了]蒽-9,11-二酮衍生物。J.杂环化​​学。（2011）。
• Molecular Iodine–Catalyzed One-Pot Synthesis of Tetrahydrobenzo[<i>a</i>]xanthene-11-one and Diazabenzo[<i>a</i>]anthracene-9,11-dione Derivatives
  作者：Xiao-Jun Sun、Jian-Feng Zhou、Pu-Su Zhao

  DOI：10.1080/00397911.2010.541966

  日期：2012.5.15

  Abstract An efficient one-pot condensation of β-naphthol, aldehydes, and cyclic 1,3-dicarbonyl compounds has been achieved with molecular iodine as a catalyst, thus a variety of tetrahydrobenzo[a]xanthene-11-one and diazabenzo[a]anthracene-9,11-dione derivatives were prepared in good yields. GRAPHICAL ABSTRACT

  摘要 以分子碘为催化剂，实现了β-萘酚、醛类和环状1,3-二羰基化合物的高效一锅缩合，从而得到多种四氢苯并[a]呫吨-11-酮和二氮杂苯并[a]蒽-9,11-二酮衍生物以良好的产率制备。图形概要
• 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。
• Green synthesis of benzochromenopyrimidines in the presence of MWCNTs@SiO2/MSA as a new and effective solid acid catalyst under microwave irradiation
  作者：Masoumeh Ahmadi、Leila Moradi、Masoud Sadeghzadeh

  DOI：10.1016/j.molstruc.2021.130183

  日期：2021.7

  A new and green synthesis of benzochromenopyrimidine derivatives is efficiently catalyzed by supported meglumine sulfonic acid on multiwalled carbon nanotube surfaces (MWCNTs@SiO2/MSA). Preparation of catalyst was performed through a simple and convenient method and characterized using FTIR, FESEM, TGA and EDX techniques. This recyclable catalyst provided a green and soft strategy to solvent-free synthesis

  负载的葡甲胺磺酸在多壁碳纳米管表面（MWCNTs @ SiO 2 / MSA ）上有效催化了一种新的绿色苯并铬嘧啶衍生物的合成。催化剂的制备通过简单方便的方法进行，并使用FTIR，FESEM，TGA和EDX技术进行了表征。这种可循环使用的催化剂为微波辐射下无溶剂合成苯并色氨并嘧啶衍生物提供了绿色而又柔软的策略。提出的方案是一种使用新型高效固体酸催化剂以高产率至优异产率合成苯并色氮嘧啶的安全，环保，便捷的方法。