2-amino-4-methyl-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile | 241466-09-1

• 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-methyl-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile
• 英文别名: 2-Amino-4-methyl-4H-pyrano[3,2-c]coumarin-3-carbonitrile；2-Amino-4-methyl-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile；2-amino-4-methyl-5-oxo-4H-pyrano[3,2-c]chromene-3-carbonitrile
• CAS: 241466-09-1
• 化学式: C₁₄H₁₀N₂O₃
• 分子量: 254.245
• InChiKey: HISMJRIIQSDFJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  2-amino-4-methyl-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile 在 盐酸羟胺 、 sodium acetate 、 溶剂黄146 作用下， 反应 3.0h， 以72%的产率得到3-Amino-5-methyl-1H-tyrazolo[3',4':6,5]pyrano[3,2-c]coumarine
  参考文献：
  名称：

  Abdel Hafiz; Hussein; Mahmoud, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1999, vol. 54, # 12, p. 1568 - 1572

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基香豆素 、 1,1-dicyanopropene 在 吗啉 作用下， 以 乙醇 为溶剂， 反应 24.5h， 以2.34 g的产率得到2-amino-4-methyl-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile
  参考文献：
  名称：

  Aliphatic aldehydes in multicomponent syntheses of 4-alkyl-substituted partially hydrogenated quinolines, fused 4H-pyrans, and 2-amino-4-ethyl-5-methylbenzene-1,3-dicarbonitrile

  摘要：

  The Knoevenagel condensation of aliphatic aldehydes with CH acids, malonodinitrile, cyanothioacetamide, cyclohexane-1,3-dione, dimedone, 4-hydroxycoumarin, 3-aminophenol, and N-(cyclohex-1-enyl)morpholine leads to formation of 4-alkyl-substituted partially hydrogenated quinolines, fused 4H-pyrans, and 2-amino-4-ethyl-5-methylbenzene-1,3-dicarbonitrile. The structure of the latter was proved by the X-ray diffraction data.

  DOI：

  10.1134/s1070428006040142

文献信息

• 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。
• Another application of (NH₄)₄₂[Mo^VI₇₂Mo^V₆₀O₃₇₂(CH₃COO)₃₀(H₂O)₇₂] as a highly efficient recyclable catalyst for the synthesis of dihydropyrano[3,2-<i>c</i>]chromenes
  作者：Marziyeh Rohaniyan、Abolghasem Davoodnia、Ahmad Nakhaei

  DOI：10.1002/aoc.3479

  日期：2016.8

  catalyst for the synthesis of heterocyclic compounds, in this paper, we report another application of this attractive catalyst in the synthesis of 2‐amino‐5‐oxo‐4,5‐dihydropyrano[3,2‐c]chromene‐3‐carbonitriles via a one‐pot three‐component reaction of 4‐hydroxycoumarin, aldehydes and malononitrile. The reactions occur in ethanol–water as solvent at room temperature and the process is operative with

  在我们先前关于（NH 4）42 [Mo VI 72 Mo V 60 O 372（CH 3 COO）30（H 2 O）72 ]的应用的继续研究中，一种Keplerate型巨球纳米多孔异聚氧钼酸盐作为杂环化合物合成的催化剂，在本文中，我们报告了这种有吸引力的催化剂在2-氨基-5-氧代-4-4，5-二氢吡喃[3,2- c通过4-羟基香豆素，醛和丙二腈的一锅三组分反应生成] 3-亚甲基苯腈。该反应在室温下以乙醇-水为溶剂发生，并且该过程可与各种醛一起操作，从而以高收率得到相应的产物。该方案的其他有益特性包括反应时间短，后处理简单，催化剂的可回收性和可重复使用性（最多可连续运行五次）。版权所有©2016 John Wiley＆Sons，Ltd.
• 4-Hydroxycoumarin in heterocyclic synthesis
  作者：A.H Bedair、Nagwa A El-Hady、M.S.Abd El-Latif、A.H Fakery、A.M El-Agrody

  DOI：10.1016/s0014-827x(00)00097-5

  日期：2000.12

  The synthesis of new [1]benzopyrano[3',4':5,6]pyrano[2,3-d]pyrimidines and related heterocycles has been reported. The key intermediate 2-amino-3-cyano-4-methyl-4H,5H-pyrano[3,2-c][1]benzopyran-5-one (3) was obtained in one pot synthesis from the reaction of 4-hydroxycoumarin and acetaldehyde-malononitrile (2). The antimicrobial screening was performed for some of the synthesized compounds.

  已经报道了新的[1]苯并吡喃并[3'，4'：5,6]吡喃并[2,3-d]嘧啶和相关杂环的合成。一锅合成法由4-的反应制得关键中间体2-氨基-3-氰基-4-甲基-4H，5H-吡喃并[3,2-c] [1]苯并吡喃-5-酮（3）羟基香豆素和乙醛-丙二腈（2）。对一些合成的化合物进行了抗菌筛选。
• 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
  作者：Mehdi Khoobi、Masoumeh Alipour、Alireza Moradi、Amirhossein Sakhteman、Hamid Nadri、Seyyede Faeze Razavi、Mehdi Ghandi、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1016/j.ejmech.2013.07.045

  日期：2013.10

  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.
• El-Agrody; Abd El-Latif; Fakery, Journal of Chemical Research, 2000, vol. 2000, # 1, p. 26 - 27
  作者：El-Agrody、Abd El-Latif、Fakery、Bedair

  DOI：——

  日期：——