3-amino-1-(4-bromophenyl)-5-oxo-1,5-dihydropyrano[2,3-c]chromene-2-carbonitrile | 1332625-46-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-amino-1-(4-bromophenyl)-5-oxo-1,5-dihydropyrano[2,3-c]chromene-2-carbonitrile
• 英文别名: 3-amino-2-cyano-5-oxo-1-(4-bromophenyl)-1,5-dihydropyrano[2,3-c]chromene；3-amino-1-(4-bromophenyl)-1,5-dihydro-5-oxopyrano[2,3-c]chromene-2-carbonitrile；3-amino-1-(4-bromophenyl)-5-oxo-1H-pyrano[2,3-c]chromene-2-carbonitrile
• CAS: 1332625-46-3
• 化学式: C₁₉H₁₁BrN₂O₃
• 分子量: 395.212
• InChiKey: VNGBHDNOILHEAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羟基香豆素 、 对溴苯甲醛 、 丙二腈 在 C₁₂H₂₄O₆*Na⁽¹⁺⁾*C₆H₄ClO₂S^(1-) 作用下， 以 乙醇 、 水 为溶剂， 反应 0.42h， 以92%的产率得到3-amino-1-(4-bromophenyl)-5-oxo-1,5-dihydropyrano[2,3-c]chromene-2-carbonitrile
  参考文献：
  名称：

  一种新的基于冠醚的离子液体，可作为绿色和多功能有机催化剂，用于三组分合成1,5-二氢吡喃并[2,3-c]色烯衍生物

  摘要：

  据报道，在一系列新型冠的存在下，芳族醛，丙二腈和3-羟基香豆素的三组分反应是一种简单而绿色的合成1,5-二氢吡喃并[2,3-c]色烯衍生物的方法。回流条件下，在H2O / EtOH（1：1）中生成基于醚的离子液体（基于CE的IL）。通过与苯亚磺酸钠衍生物螯合的18-crown-6或二苯并18-crown-6合成了基于CE的新型IL，并用作绿色环保的有机催化剂。该方法具有一些优点，例如水性反应介质，稳定的催化剂，更清洁的反应曲线和在短的反应时间内高产率的产物。

  DOI：

  10.2174/1570178616666190620124947

文献信息

• Synthesis of a SO3H-bearing carbonaceous solid catalyst, PEG–SAC: application for the easy access to a diversified library of pyran derivatives
  作者：Sanjay Paul、Sirshendu Ghosh、Pranabes Bhattacharyya、Asish R. Das

  DOI：10.1039/c3ra42352b

  日期：——

  A SO3H-bearing carbonaceous solid catalyst (PEG–SAC) has been synthesized through sulfonation followed by a hydrothermal carbonization method from renewable resources like polyethylene glycol. The biodegradable catalyst was characterized by XRD, TEM, FT-IR and EDX. The surface area and pore diameter of the catalyst were determined from a nitrogen adsorption–desorption isotherm experiment. A highly

  通过磺化，然后通过水热碳化法，从可再生资源（如聚乙二醇）中合成了一种含SO 3 H的碳质固体催化剂（PEG-SAC）。通过XRD，TEM，FT-IR和EDX对可生物降解的催化剂进行了表征。催化剂的表面积和孔径通过氮吸附-解吸等温线实验确定。高度收敛，高效且实用的PEG-SAC催化异环化方案，用于合成多样化的文库吡喃融合的杂环支架已被证明。建立该合成遵循组辅助纯化（GAP）化学过程，可避免传统色谱分离。重结晶纯化似乎是传统经典方法的一种很好的替代方法，表明碳基催化剂在生产过程中非常有效。吡喃稠合的杂环分子。水性反应介质，催化剂的易于回收和产物的高收率使得该方案具有吸引力，可持续性和经济性。
• Heterogeneous ditopic ZnFe₂O₄catalyzed synthesis of 4H-pyrans: further conversion to 1,4-DHPs and report of functional group interconversion from amide to ester
  作者：Paramita Das、Arghya Dutta、Asim Bhaumik、Chhanda Mukhopadhyay

  DOI：10.1039/c3gc42095g

  日期：——

  Highly stable, environmentally benign ZnFe2O4 nanopowder was prepared, characterized and applied in the one-pot, three-component synthesis of 4H-pyrans in water. The ZnFe2O4 catalyst provides both acidic (Fe3+) and basic functionalities (O2−) as the reaction requires. The advantages of this method lie in its simplicity, cost effectiveness, environmental friendliness and easier scaling up for large scale synthesis. Water was exploited both as a reaction medium as well as a medium for synthesis of the catalyst. Moreover, water was the only byproduct. The present report puts forward an application of 4H-pyrans for the synthesis of 1,4-DHPs. This is the first attempt towards the synthesis of 4H-pyran-3-carboxylate from 4H-pyran-3-carboxamide. The corresponding functional group interconversion from amide to ester is rare in organic synthesis.

  成功制备、表征并应用了一种稳定且对环境友好的ZnFe2O4纳米粉，在水相中实现了4H-吡喃的一锅法三组分合成。ZnFe2O4催化剂同时提供了反应所需的酸性（Fe3+）和碱性（O2−）功能。该方法的优势在于其简单性、成本效益、环境友好性以及更易于放大进行大规模合成。水既被用作反应介质，也被用作催化剂的合成介质。此外，水是唯一的副产品。本报告提出了一种应用4H-吡喃合成1,4-二氢吡啶（1,4-DHPs）的方法。这是首次尝试从4H-吡喃-3-甲酰胺合成4H-吡喃-3-羧酸酯。在有机合成中，从酰胺到酯的功能团转换是罕见的。
• New Crown Ether-Based Ionic Liquids as a Green and Versatile Organocatalyst for Three-Component Synthesis of 1,5-Dihydropyrano[2,3- c]chromene Derivatives
  作者：Iman Mohammadzadeh、Ali Asadipour、Abbas Pardakhty、Mehdi Abaszadeh

  DOI：10.2174/1570178616666190620124947

  日期：2020.2.19

  3-c]chromene derivatives has been reported by three-component reaction of aromatic aldehydes, malononitrile, and 3-hydroxycoumarin in the presence of a series of novel crown ether-based ionic liquids (CE-based ILs) in H2O/EtOH (1:1), under the reflux conditions. The novel CE-based ILs have been synthesized by 18-crown-6 or dibenzo 18-crown-6 chelated with sodium benzenesulfinate derivatives and used as

  据报道，在一系列新型冠的存在下，芳族醛，丙二腈和3-羟基香豆素的三组分反应是一种简单而绿色的合成1,5-二氢吡喃并[2,3-c]色烯衍生物的方法。回流条件下，在H2O / EtOH（1：1）中生成基于醚的离子液体（基于CE的IL）。通过与苯亚磺酸钠衍生物螯合的18-crown-6或二苯并18-crown-6合成了基于CE的新型IL，并用作绿色环保的有机催化剂。该方法具有一些优点，例如水性反应介质，稳定的催化剂，更清洁的反应曲线和在短的反应时间内高产率的产物。
• One-pot synthesis of dihydropyrano[2,3-c]chromenes via a three component coupling of aromatic aldehydes, malononitrile, and 3-hydroxycoumarin catalyzed by nano-structured ZnO in water: a green protocol
  作者：Sanjay Paul、Pranabes Bhattacharyya、Asish R. Das

  DOI：10.1016/j.tetlet.2011.06.101

  日期：2011.9

  An efficient and green protocol for the synthesis of dihydropyrano[2,3-c]chromene derivatives by one-pot, three component coupling reaction of aromatic aldehyde, malononitrile, and 3-hydroxycoumarin has been developed using nano-structured ZnO as the catalyst. The formation of self-assembled organic nanofiber arising from low-molecular-weight molecules has also been performed. The optical properties of the nano-structured organic molecules were studied. (C) 2011 Elsevier Ltd. All rights reserved.
• Patra, Amarendra; Mahapatra, Tanusri, Journal of the Indian Chemical Society, 2012, vol. 89, # 7, p. 925 - 932
  作者：Patra, Amarendra、Mahapatra, Tanusri

  DOI：——

  日期：——