2-amino-5-oxo-4-(pyridin-3-yl)-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile | 300804-37-9

• 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: 2-amino-5-oxo-4-(pyridin-3-yl)-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile
• 英文别名: 2-Amino-5-oxo-4-pyridin-3-yl-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile；2-amino-5-oxo-4-pyridin-3-yl-4H-pyrano[3,2-c]chromene-3-carbonitrile
• CAS: 300804-37-9
• 化学式: C₁₈H₁₁N₃O₃
• 分子量: 317.304
• InChiKey: FJYAQUOTZFKJKE-UHFFFAOYSA-N

物化性质

• 沸点：
  666.1±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  98.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-5-oxo-4-(pyridin-3-yl)-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile 、 邻氯氯苄 在 potassium iodide 作用下， 以 乙腈 为溶剂， 以87%的产率得到3-(2-amino-3-cyano-5-oxo-4,5-dihydropyrano[3,2-c]chromen-4-yl)-1-(2-chlorobenzyl)pyridinium chloride
  参考文献：
  名称：

  Design, synthesis, biological evaluation and docking study of 5-oxo-4,5-dihydropyrano[3,2-c]chromene derivatives as acetylcholinesterase and butyrylcholinesterase inhibitors

  摘要：

  A series of fused coumarins namely 5-oxo-4,5-dihydropyrano[3,2-c]chromenes linked to N-benzylpyridinium scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The 1-(4-fluorobenzyl)pyridinium derivative 6g showed the most potent anti-AChE activity (IC50 value = 0.038 mu M) and the highest AChE/BuChE selectivity (SI > 48). The docking study permitted us to rationalize the observed structure affinity relationships and to detect possible binding modes. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.038
• 作为产物：
  描述：

  3-吡啶甲醛 在 silica supported 3-(2-hydroxybenzylamino)propyl magnetic nanocatalyst 作用下， 以 水 为溶剂， 反应 0.58h， 生成 2-amino-5-oxo-4-(pyridin-3-yl)-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile
  参考文献：
  名称：

  Design, synthesis, biological evaluation and docking study of 5-oxo-4,5-dihydropyrano[3,2-c]chromene derivatives as acetylcholinesterase and butyrylcholinesterase inhibitors

  摘要：

  A series of fused coumarins namely 5-oxo-4,5-dihydropyrano[3,2-c]chromenes linked to N-benzylpyridinium scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The 1-(4-fluorobenzyl)pyridinium derivative 6g showed the most potent anti-AChE activity (IC50 value = 0.038 mu M) and the highest AChE/BuChE selectivity (SI > 48). The docking study permitted us to rationalize the observed structure affinity relationships and to detect possible binding modes. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.038

文献信息

• A synergetic role of Aegle marmelos fruit ash in the synthesis of biscoumarins and 2-amino-4H-chromenes
  作者：Rupesh C. Patil、Sachinkumar K. Shinde、Uttam P. Patil、Appasaheb T. Birajdar、Suresh S. Patil

  DOI：10.1007/s11164-020-04367-6

  日期：2021.4

  Abstract A dry rind of Aegle marmelos (bael) fruit ash as a synergetic alternative material to an expensive, toxic and corrosive catalysts for the synthesis of biscoumarins and 2-amino-4H-chromenes at ambient temperature in water is reported. The spectroscopic evidence from EDX, FTIR, XRD and SEM analysis of bael fruit ash supports the presence of metal oxides, carbonates and hydroxides which are intensely

  摘要 的干燥果皮木橘（巴尔）水果灰分作为协同替代材料昂贵，有毒和腐蚀性催化剂biscoumarins的合成和2-氨基-4- ħ -chromenes在水环境温度被报告。来自EDL，FTIR，XRD和SEM分析的光谱学证据证明了贝尔果灰的存在，这些金属氧化物，碳酸盐和氢氧化物的存在对反应的加速起着至关重要的作用。该协议的显着特征是利用生物废物，具有成本效益，可回收和可生物降解的催化系统，该系统可在短反应时间内提供良好或优异的收率。 图形摘要
• Tris-hydroxymethylaminomethane (THAM): a novel organocatalyst for a environmentally benign synthesis of medicinally important tetrahydrobenzo[b]pyrans and pyran-annulated heterocycles
  作者：Kapil S. Pandit、Pramod V. Chavan、Uday V. Desai、Makarand A. Kulkarni、Prakash P. Wadgaonkar

  DOI：10.1039/c4nj02346c

  日期：——

  A simple, efficient and environmentally benign protocol has been developed for the one-pot, multicomponent synthesis of medicinally important tetrahydrobenzo[b]pyrans and pyran-annulated heterocycles using a commercially available, inexpensive, non-toxic, and biodegradable tris-hydroxymethylaminomethane (THAM) as a novel organocatalyst. Ambient reaction conditions, wide scope, avoidance of conventional

  已经开发了一种简单，有效且对环境无害的方案，用于使用市售，廉价，无毒且可生物降解的三羟甲基甲基甲烷（THAM）一锅，多组分合成重要的药用四氢苯并[ b ]吡喃和吡喃环杂环）作为新型有机催化剂。环境反应条件，宽范围，避免常规分离以及纯化技术以及催化剂连续五次运行的可重复使用性提高了该多组分反应规程歧管的实用性。
• Crown ether complex cation ionic liquids (CECILs) as environmentally benign catalysts for three-component synthesis of 4,5-dihydropyrano[3,2-c]chromene and 4,5-dihydropyrano[4,3-b]pyran derivatives
  作者：Mehdi Abaszadeh、Mohammad Seifi

  DOI：10.1007/s11164-014-1855-7

  日期：2015.10

  Crown ether complex cation ionic liquids (CECILs) catalyze three-component reaction of aromatic aldehydes, malononitrile, and 4-hydroxycoumarin or 4-hydroxy-6-methylpyrone, in EtOH under reflux, for synthesis of 4,5-dihydropyrano[3,2- c ]chromene and 4,5-dihydropyrano[4,3- b ]pyran derivatives. CECILs are environmentally benign, easily obtained, stable catalysts. High conversion, short reaction times

  冠醚络合物阳离子离子液体（CECIL）在EtOH中回流下催化芳香醛，丙二腈和4-羟基香豆素或4-羟基-6-甲基吡喃酮的三组分反应，合成4,5-二氢吡喃[3,2] - c ^ ]色和4,5-二氢吡喃并[4,3- b ]吡喃衍生物。CECIL是对环境无害，易于获得的稳定催化剂。高转化率，较短的反应时间和更清洁的反应曲线是该方法的一些优势。
• (CTA)₃[SiW₁₂]–Li⁺–MMT: a novel, efficient and simple nanocatalyst for facile and one-pot access to diverse and densely functionalized 2-amino-4H-chromene derivatives via an eco-friendly multicomponent reaction in water
  作者：Esmayeel Abbaspour-Gilandeh、Mehraneh Aghaei-Hashjin、Asieh Yahyazadeh、Hadi Salemi

  DOI：10.1039/c6ra09818e

  日期：——

  the procedure, it was feasible to synthesize 2-amino-3-cyano-pyrano[3,2-c]chromen-5(4H)-one (4a–4y), 2-amino-3-cyano-pyrano[3,2-c]quinolin-5(4H)-one (6a–6s), 2-amino-3-cyano-7,8-dihydro-4H-chromen-5(6H)-one (8a–8u), 2-amino-3-cyano-pyrano[4,3-b]pyran-5(4H)-one (12a–12f), 2-amino-3-cyano-pyrano[3,2-c]pyridine-6(5H)-one (13a–13f), and 1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-dione (14a–14f). The structure

  一个简单的，容易且高效一锅合成药学有趣多样种类官能2-氨基-4-的ħ色烯由芳香醛，丙二腈（或氰基乙酸乙酯）的一个简单的三组分反应和多样化的烯醇化的C-据报道，在催化量的（CTA）3 [SiW 12 ] –Li + –MMT存在下，H活化的酸性化合物是一种新颖，环保，可重复使用且很有希望的纳米催化剂，可以在回流水中进行反应。根据该程序，合成2-氨基-3-氰基-吡喃并[3,2 - c ] chromen-5（4 H）-一（4a–4y），2-氨基-3-氰基-吡喃是可行的。[3,2 - c ]喹啉-5（4H）一（6a–6s），2-amino-3-cyano-7,8-dihydro-4 H -chromen-5（6 H）一（8a–8u），2-amino-3-cyano- pyrano [4,3- b ] pyran-5（4 H）-one（12a-12f），2-amino-3-cyano-pyrano
• Urea-functionalized silica-coated Fe3−x Ti x O4 magnetic nanoparticles: as highly efficient and recyclable heterogeneous nanocatalyst for synthesis of 4H-chromene and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives
  作者：Davood Azarifar、Omolbanin Badalkhani、Younes Abbasi、Morteza Hasanabadi

  DOI：10.1007/s13738-016-0989-5

  日期：2017.2

  highly efficient and recoverable heterogeneous nanocatalyst for one-pot three-component reactions under mild conditions for the synthesis of diverse range of 5-oxo-dihydropyrano[3,2-c]chromenes known as coumarins and 1H-pyrazolo[1,2-b] phthalazine-5,10-diones in high yields. Simple isolation of the products, use of green solvent, and magnetically easy isolation and reusability of the catalyst with no

  制备了新型的尿素官能化的二氧化硅包覆的磁性核-壳Fe 3− x Ti x O 4纳米颗粒，并通过不同方法进行了充分表征，例如傅立叶变换红外光谱，能量色散X射线光谱，场发射扫描电子显微镜，分辨率透射电子显微镜，振动样品磁力计，X射线衍射和热重分析。这些磁性纳米粒子已被研究为在温和条件下用于一锅三组分反应的高效且可回收的多相纳米催化剂，用于合成多种范围的5-氧代-二氢吡喃并[3,2-c]色烯，称为香豆素和1 H -pyrazolo [1,2-b]邻苯二甲酰5,10-二酮，收率高。产品的简单分离，绿色溶剂的使用以及磁性上的分离和催化剂的易重用性而又没有明显的活性损失是本方法的主要优点。