2-amino-4-(3-flourophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile | 326915-65-5

• 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-(3-flourophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile
• 英文别名: 2-amino-4-(3-fluorophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile；2-amino-5-oxo-4-(3-fluorophenyl)-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile；2-amino-4-(3-fluorophenyl)-3-cyano-4H,5H-pyrano[3,2-c] chromene-5-one；2-amino-4-(3-flourophenyl)-3-cyano-4H,5H-pyrano[3,2-c]chromene-5-one；2-amino-4-(3-fluorophenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene；2-amino-4-(3-fluorophenyl)-5-oxo-4H-pyrano[3,2-c]chromene-3-carbonitrile
• CAS: 326915-65-5
• 化学式: C₁₉H₁₁FN₂O₃
• 分子量: 334.306
• InChiKey: GBXPIYAYBPEBIH-UHFFFAOYSA-N

物化性质

• 熔点：
  241-242 °C(Solv: ethanol (64-17-5))
• 沸点：
  627.8±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-4-(3-flourophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile 、 环己酮 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以92%的产率得到8-amino-7-(3-fluorophenyl)-9,10,11,12-tetrahydrochromeno[3',4'5,6]pyrano[2,3-b]quinolin-6(7H)-one
  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
• 作为产物：
  描述：

  3-氟苯甲醛 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-(3-flourophenyl)-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

• 2-氨基-4-(3-氟甲基苯)-3-氰基-5-氧代-4H, 5H-吡喃酮及其应用
  申请人：江苏美思康医疗科技有限公司

  公开号：CN107141300B

  公开（公告）日：2019-03-22

  本发明涉及2‑氨基‑4‑(3‑氟苯)‑3‑氰基‑5‑氧代‑4H,5H‑吡喃酮化合物及其应用。所涉及的化合物结构式如式Ⅰ所示。所涉及的应用为所涉及化合物用于制备抗金黄色葡萄球菌生物膜制剂的应用。
• One-Pot Synthesis of Biscoumarin and Dihydropyrano[c]chromene Derivatives in the Presence of Organocatalysts under Solvent-Free Conditions
  作者：Reza Heydari、Fahimeh Shahrekipour

  DOI：10.2174/1570178613666160728122122

  日期：2016.9.21

  A simple and efficient synthesis of biscoumarin and dihydropyrano[c]chromene derivatives using catalytic amounts of imidazole or isoquinoline as organocatalyst under solvent-free conditions is reported. The present procedure offers advantages such as high to excellent yields, short reaction times, inexpensive operation, solvent-free conditions, reduced environmental consequences and simple workup.

  据报道，在无溶剂条件下，使用催化量的咪唑或异喹啉作为有机催化剂可以简单有效地合成双香豆素和二氢吡喃并[c]色烯衍生物。本方法提供了诸如高至优异的产率，短的反应时间，廉价的操作，无溶剂的条件，减少的环境影响和简单的后处理的优点。
• Domino Knoevenagel condensation, Michael addition, and cyclization using ionic liquid, 2-hydroxyethylammonium formate, as a recoverable catalyst
  作者：H.R. Shaterian、M. Arman、F. Rigi

  DOI：10.1016/j.molliq.2010.11.010

  日期：2011.1

  Knoevenagel condensation reaction of aromatic aldehydes with malononitrile or dimedone was investigated. Also, the three-component and one-pot synthesis of 2-amino-5-oxo-4-aryl-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile derivatives by condensing 4-hydroxycoumarin, aldehydes and malononitriles using a catalytic amount of 2-hydroxyethylammonium formate as an effective ionic liquid without using any additional

  研究了芳香醛与丙二腈或二甲酮的Knoevenagel缩合反应。此外，通过缩合4-羟基香豆素，醛类和醛类化合物的三组分一锅合成2-氨基-5-氧代-4-芳基-4,5-二氢吡喃并[3,2-c]亚甲基-3-甲腈衍生物。报道了在室温下在无溶剂条件下使用催化量的甲酸2-羟乙基铵作为有效的离子液体而未使用任何其他助催化剂的丙二腈。此外，以极高的收率，以高原子效率进行了多米诺Knoevenagel缩合反应，共轭加成反应和环化反应，从而制备了四氢苯并[b]吡喃和螺环吲哚衍生物。
• Green chemistry approach: sodium fluoride-catalyzed highly efficient microwave irradiation-assisted synthesis of substituted chromene derivatives in aqueous medium
  作者：K. Fabitha、C. G. Arya、Munugala Chandrakanth、Janardhan Banothu

  DOI：10.1007/s11164-022-04929-w

  日期：2023.3

  applications in medicinal chemistry. The multicomponent Knoevenagel–Michael reaction is one of the most efficient strategies to construct these two scaffolds. Previous efforts have been made in converting the traditional organic solvents to eco-friendly solvents including H2O generally in the presence of complex catalysts. Here we present our work of using sodium fluoride (NaF) as the catalyst to synthesize

  2-Amino-4 H -benzo[ H ]chromene-3-carbonitrile 和 2-amino-5-oxo-4 H ,5 H -pyrano[3,2- c ]chromene-3-carbonitrile 是两个重要的药效团，具有广泛的在药物化学中的应用。多组分 Knoevenagel-Michael 反应是构建这两种支架的最有效策略之一。之前已经在将传统有机溶剂转化为包括 H 2在内的环保溶剂方面做出了努力O 通常在复杂的催化剂存在下。在这里，我们介绍了我们使用氟化钠 (NaF) 作为催化剂从 α-或 β-萘酚或 4-羟基香豆素开始合成范围广泛的两种底物的工作。在微波辐射条件下使用 12 mol% NaF，反应在 15-25 分钟内完成，所有产率均超过 85%。通过用H 2 O洗涤简单地纯化反应产物并且可以通过用MeOH结晶进一步纯化。对绿色化学相关参数的分析表明，目前
• Acidic ionic liquids immobilized on nano silica sulfuric acid for highly effective catalytic synthesis of 4H-pyrano[2,3-c]pyrazole and dihydropyrano[c]chromene derivatives
  作者：Nasir Iravani、Mosadegh Keshavarz、Layla A. Taib

  DOI：10.1007/s11164-023-05105-4

  日期：2023.10

  the non-covalent immobilization of protic acidic ionic liquids on nano silica sulfuric acid. Initially, two organic zwitterions were prepared by reacting 1,4-dimethylpiperazine with 1,4-butane sultone under varying molar ratios and reaction temperatures. The resulting 1,4-dimethylpiperazinum functionalized mono- or bis-butyl sulfonate organic salts were then anchored onto nano silica sulfuric acid using

  我们报告了一种简单、干净、直接的方法，用于将质子酸性离子液体非共价固定在纳米二氧化硅硫酸上。最初，通过使 1,4-二甲基哌嗪与 1,4-丁烷磺内酯在不同的摩尔比和反应温度下反应来制备两种有机两性离子。然后使用非共价离子对固定方法将所得的 1,4-二甲基哌嗪官能化单或双丁基磺酸有机盐锚定到纳米二氧化硅硫酸上。接下来，使用各种技术对制备的催化剂进行了全面表征，包括 FTIR、1 H 和13 C NMR、SEM、EDX、TEM、TGA 和 BET。最后，研究了所得有机-无机纳米杂化物的催化性能，用于合成 4 种H-吡喃并[2,3-c]吡唑和3,4-二氢吡喃[c]色烯衍生物。这些离子对固定的质子离子液体提供了简化且经济高效的固定过程，无需偶联剂或复杂的化学反应即可锚定在载体上，并且与非载体形式相比，具有简单的回收和可重复使用性，同时具有改进的热稳定性，使他们成为更好的选择。