12-(3-chlorophenyl)-8,12-dihydro-8,10-dimethyl-9Hnaphtho[1’,2’:5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-dione | 1369964-62-4

• 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-(3-chlorophenyl)-8,12-dihydro-8,10-dimethyl-9Hnaphtho[1’,2’:5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-dione
• 英文别名: 12-(3-chlorophenyl)-8,12-dihydro-8,10-dimethyl-9H-naphtho[1',2':5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-dione；12-(3-chlorophenyl)-8,10-dimethyl-8,12-dihydro-9H-naphtho[1’,2’:5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-dione；18-(3-Chlorophenyl)-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-(3-chlorophenyl)-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: 1369964-62-4
• 化学式: C₂₃H₁₇ClN₂O₃
• 分子量: 404.853
• InChiKey: AUTUKUUHTDLZFL-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 、 3-氯苯甲醛 、 2-萘酚 在 ZrOCl₂ supported nano TiO₂ 作用下， 以 neat (no solvent) 为溶剂， 反应 0.47h， 以82%的产率得到12-(3-chlorophenyl)-8,12-dihydro-8,10-dimethyl-9Hnaphtho[1’,2’:5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-dione
  参考文献：
  名称：

  ZrOCl2 / nano TiO2作为无溶剂条件下一锅合成萘并吡喃并嘧啶的高效催化剂。

  摘要：

  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。

  DOI：

  10.17344/acsi.2015.1567

文献信息

• Efficient Lactic Acid-catalyzed Route to Naphthopyranopyrimidines under Solvent-free Conditions
  作者：Fatemeh Noori Sadeh、Nourallah Hazeri、Malek Taher Maghsoodlou、Mojtaba Lashkari

  DOI：10.1080/00304948.2017.1260395

  日期：2017.1.2

  interesting heterocyclic scaffolds and libraries of biologically active molecules. They have several notable advantageous feature such as flexibility, operational simplicity, simple purification of products, minimum reaction steps, time and energy savings, and a high degree of atom economy. In order to avoid the use of organic solvents, solventfree systems are also important for green chemical syntheses. Solvent-free

  多组分反应 (MCR) 是关键，因为它们在生成有趣的杂环支架和生物活性分子库方面具有多功能性。它们具有几个显着的优点，例如灵活性、操作简单、产品纯化简单、反应步骤最少、节省时间和能源以及高度的原子经济性。为了避免使用有机溶剂，无溶剂系统对于绿色化学合成也很重要。无溶剂反应还具有其他优点，包括操作简单、反应时间减少以及由于试剂的相容性而提高产率。萘并吡喃嘧啶是制备生物活性产品的关键组成部分，具有抗菌、抗惊厥、抗菌、和抗真菌活性。最近，Marugan 报道了治疗睡眠和焦虑症的新药（图 1）。以前用于通过醛与 b-萘酚（或 2,7-二羟基萘）和 1,3-二甲基巴比妥酸的缩合制备萘并吡喃嘧啶的催化剂包括 InCl3 和 P2O5、15 I2/HOAC、16 I2、17 明矾（KAl（ SO4)2.12H2O)、18 和 ZnO 纳米颗粒。
• 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。
• Al(H₂PO₄)₃ as an efficient and recyclable catalyst for the one-pot synthesis of naphthopyranopyrimidines
  作者：Seyed Sajad Sajadikhah

  DOI：10.1039/c5ra00679a

  日期：——

  An efficient one-pot protocol has been developed for the synthesis of naphthopyranopyrimidine derivatives via a three-component reaction of aromatic aldehydes, β-naphthol and 6-amino-1,3-dimethyl uracil in the presence of Al(H₂PO₄)₃.

  已开发出一种高效的一锅法合成萘吡喹嘧啶衍生物的方案，通过芳香醛、β-萘酚和6-氨基-1,3-二甲基尿嘧啶在Al(H₂PO₄)₃存在下进行三组分反应。
• A flexible one-pot synthesis of 8,10-dimethyl-12-aryl-9H-naphto[1′,2′:5,6]pyrano[2,3-d]pyrimidine-9,11-diones catalyzed by ZnO nanoparticles under solvent-free conditions
  作者：Mahboubeh Mohaqeq、Javad Safaei-Ghomi

  DOI：10.1007/s00706-015-1411-1

  日期：2015.9

  A new, convenient, and green procedure for the synthesis of naphthopyranopyrimidine-diones is described using a one-pot multi-component reaction of beta-naphthol, 1,3-dimethylbarbituric acid, and various aryl aldehydes in the presence of ZnO nanoparticles, an effective and recyclable heterogeneous catalyst, under solvent-free conditions. This method provides excellent advantages, such as waste-free, simple work-up procedure, and excellent yield with high selectivity. The stability of the catalyst was investigated by determining its activity after recycling for six times without significant loss of its catalytic activity.
• An Efficient Solvent-Free Synthesis of Naphthopyranopyrimidines Using Heteropolyacid as an Ecofriendly Catalyst
  作者：Shivkumar S. Jalde、Hemant V. Chavan、Laxman K. Adsul、Valmik D. Dhakane、Babasaheb P. Bandgar

  DOI：10.1080/15533174.2013.783858

  日期：2014.4.21

  An efficient, one-pot, three-component synthesis of naphthopyranopyrimidines using -naphthol, aldehydes, and 6-amino-1,3-dimethyl uracil catalyzed by heteropolyacid has been achieved within a short period of time. The present methodology offers several advantages such as ecofriendly catalyst, low catalyst loading, short reaction time, simple purification procedure, and excellent yields.