2-(4-(dimethylamino)-8-methoxy-5H-chromeno[2,3-d]pyrimidin-2-yl)-5-methoxyphenol | 1242078-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(4-(dimethylamino)-8-methoxy-5H-chromeno[2,3-d]pyrimidin-2-yl)-5-methoxyphenol
• CAS: 1242078-19-8
• 化学式: C₂₁H₂₁N₃O₄
• 分子量: 379.415
• InChiKey: XUUGIZZVAAWINQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76.94
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 二甲胺 、 丙二腈 在 covalently anchored 1-(aminoethyl)-3-propylimidazolium bromide on SBA-15 作用下， 反应 0.25h， 以65%的产率得到2-(4-(dimethylamino)-8-methoxy-5H-chromeno[2,3-d]pyrimidin-2-yl)-5-methoxyphenol
  参考文献：
  名称：

  Covalently anchored 2-amino ethyl-3-propyl imidazolium bromideon SBA-15 as a green, efficient and reusable Brønsted basic ionic liquid nanocatalyst for one-pot solvent-free synthesis of benzopyranopyrimidines under ultrasonic irradiation

  摘要：

  在超声辐射下，由SBA-IM-NH₂催化制备苯并吡啶并嘧啶衍生物。

  DOI：

  10.1039/c5ra11006h

文献信息

• ZrOCl₂·8H₂O as an Efficient Catalyst for the Pseudo Four-Component Synthesis of Benzopyranopyrimidines
  作者：Hamid Reza Tavakoli、Sayed Mojtaba Moosavi、Ayoob Bazgir

  DOI：10.5012/jkcs.2013.57.2.260

  日期：2013.4.20

  An efficient and environmentally benign protocol for the pseudo four-component synthesis of benzopyranopyrimidines via condensation of salicylic aldehydes, malononitrile and various amines catalyzed by $ZrOCl_2\cdot}8H_2O$ as an inexpensive and eco-friendly catalyst with high catalytic activity under solvent-free conditions is reported. This protocol provides a new and improved method for obtaining benzopyranopyrimidines in terms of good yields, simple experimental procedure and short reaction time.

  报道了一种高效且环境友好的伪四组分合成苯并吡喃嘧啶的方法，该方法通过水杨醛、马隆腈和各种胺的缩合反应，在无溶剂条件下，采用廉价且环保的催化剂氯化锆八水合物（$ZrOCl_2\cdot}8H_2O$）进行催化，展现出高催化活性。这一方案在良好产率、简单的实验程序和短反应时间方面提供了一种新的改进方法来获得苯并吡喃嘧啶。
• Synthesis of benzopyrano[2,3-d]pyrimidines using silica-bonded N-propylpiperazine sodium N-propionate as heterogeneous solid base catalyst under solvent-free conditions
  作者：Khodabakhsh Niknam、Nassim Borazjani

  DOI：10.1007/s00706-015-1552-2

  日期：2016.6

  N-propylpiperazine sodium N-propionate is employed as a recyclable heterogeneous solid base catalyst for the synthesis of benzopyrano[2,3-d]pyrimidines through one-pot condensation reaction of salicylaldehydes, malononitrile, and secondary amines at room temperature under solvent-free conditions. The catalyst could be recycled several times without appreciable loss in catalytic activity. Graphical abstract

  摘要硅胶键合的N-丙基哌嗪N-丙酸钠被用作可回收的非均相固体碱催化剂，用于在室温下于室温下通过水杨醛，丙二腈和仲胺的一锅缩合反应合成苯并吡喃并[2,3- d ]嘧啶无溶剂条件。催化剂可以循环使用几次，而催化活性没有明显损失。 图形概要
• Novel Approaches for the Synthesis of a Library of Fluorescent Chromenopyrimidine Derivatives
  作者：Afsaneh Zonouzi、Fatemeh Hosseinzadeh、Nastaran Karimi、Roghieh Mirzazadeh、Seik Weng Ng

  DOI：10.1021/co300141j

  日期：2013.5.13

  A library of some new fluorescent chromenopyrimidine derivatives has been synthesized by new approaches. Water-promoted and one-pot reaction can produce new dialkylylamino)-5H-chromeno[2,3-d]pyrimidin-2-yl) phenols. These compounds can also be produced using domino reaction. Two parallel methods are compared. Novel N-alkyl-N-phenyl-5H-chromeno [2,3-d] -pyrimidin-4-amines and 4-alkoxy-5H-chromeno[2, 3-d]pyrimidines are synthesized by Lewis-acid catalyzed reactions. The fluorescence emission intensity of the four compounds from each of libraries after excitation in 290 nm is measured. Compound 2-(4,5-bis(N-methyl-N-phenylamino)-5H-chromeno[2,3-d]pyrimidin-2-yl)phenol was isolated as a byproduct. The details of an interesting exchangeable intramolecular H-bonding of two of the new compounds are reported by X-ray analysis data.
• Pseudo four-component synthesis of benzopyranopyrimidines
  作者：Ramin Ghahremanzadeh、Tayebeh Amanpour、Ayoob Bazgir

  DOI：10.1016/j.tetlet.2010.06.014

  日期：2010.8

  An efficient and simple method for the synthesis of new benzopyranopyrimidines via a pseudo four-component reaction of salicylic aldehydes, malononitrile and various amines in the presence of a catalytic amount of LiClO(4) is reported. The advantages of this procedure are mild reaction conditions, high yields of products and operational simplicity. (C) 2010 Elsevier Ltd. All rights reserved.