2-amino-4-(2-hydroxy-3-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile | 1449490-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-amino-4-(2-hydroxy-3-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-3-cyano-4-(2-hydroxy-3-methoxyphenyl)-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran；2-amino-4-(2-hydroxy-3-methoxyphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran
• CAS: 1449490-19-0
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: JCBDZEIQOBJXOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  105.57
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 邻香草醛 、 丙二腈 在 biosynthesized-ZnO nanocomposites on Fe₃O₄ magnetic nanoparticles 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以87%的产率得到2-amino-4-(2-hydroxy-3-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Petasites hybridus根茎水提取物绿色合成Fe3O4 / ZnO磁性核壳纳米粒子及其在吡喃衍生物合成中的应用：抗氧化剂和抗菌活性的研究

  摘要：

  在这项研究中，使用Petasites hybridus根茎水提取物作为还原剂和稳定剂，通过绿色方法合成了Fe 3 O 4 / ZnO磁性核壳纳米粒子（Fe 3 O 4 / ZnO MCNPs）。通过X射线衍射，扫描电子显微镜和能量色散X射线光谱（EDX）分析确定了Fe 3 O 4 / ZnO MCNP的形态和尺寸。Fe 3 O 4的催化活性在室温下，使用二甲酮，醛和丙二腈在乙醇中的三组分反应，可以高效/绿色制备吡喃衍生物，并以优异的收率评估/ ZnO MCNP。测量了一些合成化合物清除2,2-二苯基-1-吡啶甲基肼基的能力，结果证明了这一观察结果。此外，通过对革兰氏阳性和革兰氏阴性细菌进行圆盘扩散试验，证明了某些合成化合物的抗菌活性。圆盘扩散试验的结果表明，化合物（4c，4d，4f和4g）阻止细菌生长。

  DOI：

  10.1002/aoc.5731

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。
• Dendrimeric magnetic nanoparticle cores with Co-phthalocyanine tags and their application in the synthesis of tetrahydrobenzo[b]pyran derivatives
  作者：Mohamad Ali Zolfigol、Maliheh Safaiee、Neda Bahrami-Nejad

  DOI：10.1039/c6nj00243a

  日期：——

  A novel magnetically recoverable nanocatalyst was synthesized and used for the synthesis of tetrahydrobenzo[b]pyran derivatives under mild conditions.

  合成了一种新型的可磁回收纳米催化剂，并用于在温和条件下合成四氢苯并[b]吡喃衍生物。
• Nanorod Vanadatesulfuric Acid as a Novel, Recyclable and Heterogeneous Catalyst for the One-Pot Synthesis of Tetrahydrobenzopyrans
  作者：Masoud Nasr-Esfahani、Tooba Abdizadeh

  DOI：10.1166/jnn.2013.7592

  日期：2013.7.1

  Vanadatesulfuric acid (VSA), as a novel and heterogeneous nanorod catalyst, was used for an efficient synthesis of tetrahydrobenzo[b]pyrans using an aldehydes, 1,3-cyclohexanediones or β-ketoester and malononitrile in C2H5OH/H2O mixture under reflux conditions. VSA is prepared via the reaction of sodium metavanadate and chlorosulfonic acid in high purity. The catalyst was characterized by FT-IR, XRD, TEM and EDAX analysis. Compared to the conventional method, this method consistently has the advantage of high yields, simple workup, short reaction times and reusability of the catalyst.

  作为一种新型的非均相纳米棒催化剂，钒酸硫酸(VSA)被用于在乙醇/水混合溶剂中，通过醛、1,3-环己二酮或β-酮酯和丙二腈的回流反应，高效合成四氢苯并[b]吡喃。VSA是通过偏钒酸钠和氯磺酸反应制备得到的高纯度产物。该催化剂通过FT-IR、XRD、TEM和EDAX分析进行表征。与传统方法相比，这种方法具有产率高、操作简单、反应时间短和催化剂可重复使用等优点。
• Synthesis of Eu(III) fabricated spinel ferrite based surface modified hybrid nanocomposite: Study of catalytic activity towards the facile synthesis of tetrahydrobenzo[b]pyrans
  作者：Taiebeh Tamoradi、Bikash Karmakar、Maryam Kamalzare、Mohammad Bayat、Afsaneh Taheri Kal-Koshvandi、Ali Maleki

  DOI：10.1016/j.molstruc.2020.128598

  日期：2020.11

  The present work demonstrates a modified protocol for the synthesis of Europium (Eu) anchored iminodiacetic acid functionalized silica modified core-shell CoFe2O4 magnetic nanoparticles. This is the first report of Eu immobilized nanocomposite in the synthesis of biologically active organic compounds. The structural and physicochemical characteristics of the material were evaluated using different analytical techniques such as Fourier transformed infrared spectroscopy (FT-IR), Field Emission Scanning Electron Microscopy (FESEM), Energy Dispersive X-ray Spectroscopy (EDX), X-ray Elemental Mapping (WDX) and X-ray Diffraction study (XRD). The Eu(III)IIDA/CPTS/CoFe2O4 nanocomposite was catalytically investigated in the multicomponent green synthesis of diverse substituted tetrahydrobenzo[b]pyrans by coupling dimedone, malononitrile and a wide range of aromatic aldehydes. The magnetically retrievable catalyst was stable enough to be reused up to six consecutive times in the reaction without considerable loss in activity. (C) 2020 Elsevier B.V. All rights reserved.