2-amino-4-(2,4-dichlorophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile

• 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-4-(2,4-dichlorophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile
• 英文别名: 2-amino-4-(2,4-dichlorophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile；2-amino-4,5-dihydro-4-(2,4-dichlorophenyl)-5-oxopyrano[3,2-c]chromene-3-carbonitrile；2-amino-4-(2,4-dichlorophenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene；2-amino-4-(2,4-dichlorophenyl)-4,5-dihydro-5-oxopyrano[3,2-c]-chromene-3-carbonitrile；2-amino-4-(2,4-dichlorophenyl)-5-oxo-4H-pyrano[3,2-c]chromene-3-carbonitrile
• 化学式: C₁₉H₁₀Cl₂N₂O₃
• 分子量: 385.206
• InChiKey: SOQSCSUCGCDSLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 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

• 作为反应物：
  描述：

  环己酮 、 2-amino-4-(2,4-dichlorophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile 在 sodium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 4.5h， 以70%的产率得到8-amino-7-(2,4-dichlorophenyl)-9,10,11,12-tetrahydrochromeno[3',4':5,6]pyrano[2,3-b]quinolin-6(7H)-one
  参考文献：
  名称：

  Efficient and Facile Synthesis of Chromenopyrano[2,3-b] pyridine Derivatives Catalyzed by Sodium Carbonate

  摘要：

  在这项研究中，制备了一系列新的和已知的咔啉并吡喃并[2,3-b]吡啶衍生物。首先，根据报道的程序，使用二氧化硅碳酸钠（SSC）作为催化剂，通过对4-羟基香豆素、芳香醛和丙二腈的反应合成了吡喃并[2,3-c]咔啉衍生物。接下来，制备的吡喃并[2,3-c]咔啉与二甲基乙炔二羧酸二甲酯（DMAD）或环己酮在碳酸钠存在下反应，生成了咔啉并吡喃并[2,3-b]吡啶衍生物。该方法避免了使用昂贵的催化剂，并以优良至高收率产生了有用的潜在生物活性杂环化合物。

  DOI：

  10.17344/acsi.2020.6266
• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 (2-aminomethyl)phenol moiety on the surface of hydroxyapatite encapsulated maghemite (γ-Fe₂O₃) 作用下， 以 水 为溶剂， 反应 0.08h， 生成 2-amino-4-(2,4-dichlorophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile
  参考文献：
  名称：

  Design, synthesis, docking study and biological evaluation of some novel tetrahydrochromeno [3′,4′:5,6]pyrano[2,3-b]quinolin-6(7H)-one derivatives against acetyl- and butyrylcholinesterase

  摘要：

  Novel hybrid derivatives of two known scaffolds; tetrahydroaminoquinoline and coumarin were synthesized and evaluated for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) activities. By means of an efficient nanocatalyst, the reaction time for the syntheses of the target compounds was reduced. Subsequently, Ellman's modified method was used to evaluate the enzyme inhibitory activity of the synthesized structures. It was observed that most hybrid structures were moderate to potent inhibitors of AChE compared to Tacrine as the reference drug among which 7f with 4-fluorophenyl substituent was the most active compound (IC50 = 5 nM). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.045

文献信息

• 1-Methylimidazolium tricyanomethanide {[HMIM]C(CN)3} as a nano structure and reusable molten salt catalyst for the synthesis of tetrahydrobenzo[b]pyrans via tandem Knoevenagel-Michael cyclocondensation and 3,4-dihydropyrano[c]chromene derivatives
  作者：Mohammad Ali Zolfigol、Neda Bahrami-Nejad、Fatemeh Afsharnadery、Saeed Baghery

  DOI：10.1016/j.molliq.2016.06.069

  日期：2016.9

  An expeditious, experimentally simple and rapid 1-methylimidazolium tricyanomethanide [HMIM]C(CN)3} nano molten salt (NMS) catalyzed tandem Knoevenagel-Michael cyclocondensation procedure for the synthesis of tetrahydrobenzo[b]pyrans was described via reaction between dimedone, aromatic aldehyde and malononitrile under solvent-free conditions at room temperature. Furthermore, 3,4-dihydropyrano[c]chromene

  通过二甲酮之间的反应，描述了一种快速，实验简单且快速的三氰基甲基1-甲基咪唑鎓[HMIM] C（CN）3 }纳米熔融盐（NMS）催化串联Knoevenagel-Michael环缩合反应合成四氢苯并[ b ]吡喃的方法，室温下在无溶剂条件下的芳族醛和丙二腈。此外，在相同条件下，以[HMIM] C（CN）3 } NMS为催化量，通过4-羟基香豆素，芳香醛和丙二腈的缩合反应合成了3,4-二氢吡喃并[ c ]色烯衍生物。
• DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium
  作者：Jitender M. Khurana、Bhaskara Nand、Pooja Saluja

  DOI：10.1016/j.tet.2010.05.082

  日期：2010.7

  We have reported DBU catalyzed one-pot synthesis of 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H-benzo[g]chromenes from aldehydes, active methylene compounds malononitrile/ethyl cyanocacetate, and 4-hydroxycoumarin/4-hydroxy-6-methylpyrone/1-naphthol/2-hydroxynaphthalene-1,4-dione in water under reflux. The attractive features of this process

  我们已经报道了DBU催化一锅合成3,4-二氢吡喃并[3,2- c ]苯并二氢吡喃并[4,3- b ]吡喃，2-氨基-4 H-苯并[ h ]苯并二胺回流下得自醛，活性亚甲基化合物丙二腈/氰基乙酸乙酯和4-羟基香豆素/ 4-羟基-6-甲基吡喃酮/ 1-萘酚/ 2-羟基萘-1,4-二酮的-4 H-苯并[ g ]色酮。该方法的吸引人的特征是温和的反应条件，反应介质的可重​​复使用性，较短的反应时间，易于分离的产物以及优异的产率。
• Synthesis of a novel dendrimer core of oxo-vanadium phthalocyanine magnetic nano particles: as an efficient catalyst for the synthesis of 3,4-dihydropyrano[c]chromenes derivatives under green condition
  作者：Maliheh Safaiee、Mohammad Ali Zolfigol、Fatemeh Afsharnadery、Saeed Baghery

  DOI：10.1039/c5ra18723k

  日期：——

  Finally, catalytic activity of the prepared Fe3O4@SiO2@SiO2(CH2)3@AVOPc was examined in the synthesis of 3,4-dihydropyrano[c]chromenes derivatives. The nano catalysts provided excellent catalytic activities to yield the desired products in short reaction time, mild and green conditions under solvent-free at room temperature. The catalysts could be easily separated from the reaction mixture by a magnet

  通过将氨基钒氧代酞菁共价结合在具有3-氯丙基部分的二氧化硅包覆的磁铁矿纳米颗粒的表面上，合成了一种新型的可磁性回收的纳米催化剂。使用不同的物理化学方法（例如FT-IR光谱，X射线衍射（XRD），扫描电子显微镜（SEM），透射电子显微镜（TEM），原子力显微镜（AFM）和热重量分析（TGA），能量色散X射线能谱（EDX）和振动样品磁力分析（VSM），Brunauer-Emmett-Teller（BET），X射线荧光（XRF）和电感耦合等离子体（ICP）。最后，制备的Fe 3 O 4 @SiO 2 @SiO 2的催化活性（CH 2）3 @AVOPc在合成3,4-二氢吡喃并[c]色酮衍生物中进行了研究。纳米催化剂提供了出色的催化活性，可在较短的反应时间，温和和绿色条件下于室温下在无溶剂的条件下产生所需的产物。催化剂可以很容易地用磁铁从反应混合物中分离出来，并且可以连续八次循环使用，而不会损失任何
• A novel magnetically recyclable semi‐dendrimer catalyst‐based ethanolpyridole supported on ferrite nanoparticles (HNPs@Py) for the synthesis of biscoumarin and dihydropyrano[3,2‐ <i>c</i> ]chromene derivatives
  作者：Fatemeh Afsharnadery、Kaveh Khosravi、Mohammad Ali Zolfigol

  DOI：10.1002/aoc.6297

  日期：2021.8

  The novel organic–inorganic nanohybrid magnetic nanoparticles (HNPs@Py) were prepared by a simple method and characterized by FT-IR, XRD, FE-SEM, TGA, VSM, EDX, and MAP. The catalytic activity of this new (HNPs@Py) was studied for green synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives. The short reaction time, high yields, simple workup, and easy separation of catalyst from the

  通过简单的方法制备了新型有机-无机纳米杂化磁性纳米粒子 (HNPs@Py)，并通过 FT-IR、XRD、FE-SEM、TGA、VSM、EDX 和 MAP 进行表征。研究了这种新的 (HNPs@Py) 的催化活性，用于双香豆素和 3,4-二氢吡喃并 [ c ] 色烯衍生物的绿色合成。本协议的主要优点是反应时间短、收率高、后处理简单以及易于从反应混合物中分离催化剂。
• Mono- and Bis-2-amino-4H-pyrans: Alum Catalyzed Three- or Pseudo Five-Component Reaction of 4-Hydroxycoumarin, Malononitrile and Aldehydes
  作者：Ali Reza Karimi、Cyrus Eslami

  DOI：10.2174/157017811794697421

  日期：2011.2.1

  An efficient method for the three- or pseudo five-component synthesis of mono- and bis-2-amino-4H-pyrans in excellent yields using Alum (KAl(SO4)2.12H2O) as recyclable catalyst is described. The present methodology offers several advantages such as excellent yields, simple procedures, shorter reaction times, milder conditions and the catalysts exhibited remarkable reusable activity.

  描述了一种有效的方法，该方法使用明矾（KAl（SO4）2.12H2O）作为可循环催化剂，以优异的产率三价或假五组分合成单和双-2-氨基-4H-吡喃。本方法提供了许多优点，例如优异的产率，简单的方法，较短的反应时间，较温和的条件以及催化剂显示出显着的可重复使用的活性。