4-bromo-2-(7-bromo-4-morpholino-5H-chromeno[2,3-d]pyrimidin-2-yl)phenol | 1233188-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-bromo-2-(7-bromo-4-morpholino-5H-chromeno[2,3-d]pyrimidin-2-yl)phenol
• 英文别名: 4-bromo-2-(7-bromo-4-morpholin-4-yl-5H-chromeno[2,3-d]pyrimidin-2-yl)phenol
• CAS: 1233188-17-4
• 化学式: C₂₁H₁₇Br₂N₃O₃
• 分子量: 519.192
• InChiKey: GRSTUAXYKRZEPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  吗啉 、 丙二腈 、 5-溴水杨醛 反应 0.15h， 以90%的产率得到4-bromo-2-(7-bromo-4-morpholino-5H-chromeno[2,3-d]pyrimidin-2-yl)phenol
  参考文献：
  名称：

  Mild preparation of chromeno[2,3-d]pyrimidines catalyzed by Brønsted acidic ionic liquids under solvent-free and ambient conditions

  摘要：

  布朗斯特酸性离子液体，即2-吡咯烷铵氢硫酸盐、N-甲基-2-吡咯烷铵氢硫酸盐、N-甲基-2-吡咯烷铵二氢磷酸盐、(4-磺基丁基)三(4-磺基苯基)膦酸氢硫酸盐、三苯基(丙基-3-磺酸基)膦酸苯甲酸盐、L-脯氨酸硫酸盐和L-脯氨酸硝酸盐，在室温下无溶剂条件下催化了水杨 aldehydes、马来腈和二级胺的一锅伪四组分反应，以制备 chromeno[2,3-d]pyrimidines。催化剂表现出环境友好的特性，易于制备、储存和回收，且活动性没有明显显著损失。

  DOI：

  10.1007/s11164-012-0889-y

文献信息

• An eco-safe approach to benzopyranopyrimidines and 4H-chromenes in ionic liquid at room temperature
  作者：Amit Kumar Gupta、Kumkum Kumari、Neetu Singh、Dushyant Singh Raghuvanshi、Krishna Nand Singh

  DOI：10.1016/j.tetlet.2011.11.116

  日期：2012.2

  An environmentally benign, ionic liquid promoted multicomponent protocol to benzopyrano(2,3-d)pyrimidines and 4H-chromenes has been developed at room temperature. Results of the reaction depend on the nature of the nucleophile used in the reaction. Secondary amines result in the formation of benzopyrano(2,3-d)pyrimidines, whereas thiols give rise to 4H-chromenes under the same set of reaction conditions

  在室温下开发了对苯并吡喃并（2,3- d）嘧啶和4 H-色烯的无害环境的离子液体促进多组分方案。反应的结果取决于反应中所用亲核试剂的性质。仲胺导致苯并吡喃并（2,3- d）嘧啶的形成，而硫醇在相同的反应条件下产生4 H-色烯。
• A novel, facile, rapid, solvent free protocol for the one pot green synthesis of chromeno[2,3-d]pyrimidines using reusable nano ZnAl₂O₄– a NOSE approach and photophysical studies
  作者：Balijapalli Umamahesh、Triveni Rajashekhar Mandlimath、Kulathu I. Sathiyanarayanan

  DOI：10.1039/c4ra16263c

  日期：——

  The current protocol resulted in the preparation of an eco-friendly, highly stable, reusable nano ZnAl2O4 and for the first time this was used as an excellent catalyst for the pseudo four component synthesis of a library of fluorescent chromeno[2,3-d]pyrimidine derivatives. This novel protocol involved the grinding of salicylaldehydes, malononitrile and secondary amines in the presence of a catalytic

  目前的方案导致了生态友好，高度稳定，可重复使用的纳米ZnAl 2 O 4的制备，并且首次将其用作荧光色铬[2,3]假四组分合成的优良催化剂。 - d ]嘧啶衍生物。这种新颖的方案涉及在室温下在催化量的纳米ZnAl 2 O 4的存在下研磨水杨醛，丙二腈和仲胺，这是一种非常简单，便捷，经济高效，无溶剂的方案，并且仅需两分钟即可完成。获得具有优异产量的产品。合成的chromeno [2,3- d由于其激发态分子内质子转移（ESIPT）机理的特征，]嘧啶衍生物显示出显着的吸收和发射特性，并具有较大的斯托克位移值。纳米ZnAl 2 O 4由于具有63 m 2 g -1的较大表面积而表现出比本体更好的催化活性，并且在不损失活性的情况下被循环使用了5次。
• 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。
• Aminopropyl coated on magnetic Fe₃O₄and SBA-15 nanoparticles catalyzed mild preparation of chromeno[2,3-d]pyrimidines under ambient and solvent-free conditions
  作者：Hamid Reza Shaterian、Morteza Aghakhanizadeh

  DOI：10.1039/c2cy20543b

  日期：——

  3-Aminopropyltriethoxysilane coated on magnetic Fe3O4 nanoparticles [APTES-MNPs] and 3-aminopropyltriethoxysilane coated on SBA-15 [APTES-(SBA-15)] catalyzed efficiently the one-pot pseudo four-component reaction of salicylaldehydes, malononitrile and secondary amines for preparation of chromeno[2,3-d]pyrimidines under solvent-free conditions at room temperature. The catalysts show environmentally benign character, which can be easily prepared, stored, and recovered without obvious significant loss of activity.

  3-氨丙基三乙氧基硅烷涂覆在磁性Fe3O4纳米颗粒上（[APTES-MNPs]）和涂覆在SBA-15上的3-氨丙基三乙氧基硅烷（[APTES-(SBA-15)]）高效催化了水相无溶剂条件下，在室温下进行的水杨醛、马龙腈和二级胺的单锅伪四组分反应，以制备chromeno[2,3-d]pyrimidines。这些催化剂具有环保特性，易于制备、存储和回收，且活性损失不明显。
• Efficient One-Pot Synthesis of Quinazoline and Benzopyrano[2,3-<i>d</i>]pyrimidine Derivatives Catalyzed by<i>N</i>-Bromosulfonamides
  作者：Ramin Ghorbani-Vaghei、Mina Shirzadi-Ahodashti、Fattemeh Eslami、Seyedeh Mina Malaekehpoor、Zahra Salimi、Zahra Toghraei-Semiromi、Samira Noori

  DOI：10.1002/jhet.2570

  日期：2017.1

  N'‐tetrabromobenzene‐1,3‐disulfonamide and poly(N,N’‐dibromo‐N‐ethyl‐benzene‐1,3‐disulfonamide) were used as efficient catalysts for one‐pot synthesis of new quinazoline derivatives from various aldehydes, 2‐amino‐benzophenone, and ammonium acetate in good to excellent yields and new benzopyrano[2,3‐d]pyrimidine derivatives from salicylic aldehydes, various cyclic amines, and malononitrile in good to high yields.

  N，N，N'，N'-四溴苯-1,3-二磺酰胺和聚（N，N'-二溴N-乙基-苯-1,3-二磺酰胺）被用作高效催化剂，用于一锅合成来自各种醛的新喹唑啉衍生物，2-氨基二苯甲酮和乙酸铵，收率高至优异；来自水杨醛，各种环胺和丙二腈的新型苯并吡喃并[2,3- d ]嘧啶衍生物，收率高至高。