2-amino-4-(3,4-dihydroxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile | 326918-69-8

• 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-(3,4-dihydroxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4-(3,4-dihydroxyphenyl)-4H-chromene-3-carbonitrile；2-amino-4-(3,4-dihydroxyphenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• CAS: 326918-69-8
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: CSUIFALCJSGFHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 丙二腈 、 3,4-二羟基苯甲醛 在 5-amino-N-triethoxysilylpropyltetrazol e-1-carboxamide-based Mn complex supported on magnetic Fe₃O₄(at)SiO₂ nanoparticles 作用下， 以 乙醇 为溶剂， 以85 %的产率得到2-amino-4-(3,4-dihydroxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  氨基-三乙氧基甲硅烷基丙基-四唑-甲酰胺基锰络合物作为合成四氢苯并吡喃的有效纳米催化剂

  摘要：

  设计、制备了一种新型磁性负载氨基-三乙氧基甲硅烷基丙基-四唑-甲酰胺（ATSPTC）基锰络合物（ATSPTC-Mn催化剂）作为非均相催化剂，并通过傅里叶变换红外光谱（FT-IR）、能量-色散X射线光谱（EDX）、X射线粉末衍射（XRD）、热重分析-差热分析（​​TGA-DTA）、振动样品磁强计（VSM）、扫描电子显微镜（SEM）、透射电子显微镜（ TEM)、SEM 映射和电感耦合等离子体 (ICP) 技术。然后，将 ATSPTC-Mn 催化剂用作可重复使用的催化剂，用于芳基醛、双甲酮和丙二腈在回流乙醇中的三组分缩合反应绿色合成四氢苯并吡喃。还发现ATSPTC-Mn催化剂在合成普通四氢苯并吡喃以及双、三衍生物方面具有很高的效率。该催化剂可以很容易地通过磁场回收并重复使用七个连续的反应循环，而不会显着丧失活性。

  DOI：

  10.1016/j.catcom.2022.106523

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。
• Horsetail plant (Equisetum arvense) and horsetail plant ash: application and comparison of their catalytic activities as novel and natural porous lewis acid catalysts for the one-pot green synthesis of 2-amino-4H-chromene derivatives under solvent-free conditions
  作者：Nina Hosseini Mohtasham、Mostafa Gholizadeh

  DOI：10.1007/s13738-019-01777-1

  日期：2020.2

  area, porosity, and crystalline structure which can affect their catalytic activities. The synthesis of 2-amino-4H-chromene derivatives was performed via a one-pot three-component condensation of dimedone, malononitrile, and various aromatic aldehydes to compare their catalytic activities under solvent-free conditions. Due to its high porosity and high surface area, horsetail ash yields better results

  这项研究的目的是使用一种新型的药用多孔植物，该植物具有高含量的二氧化硅，首次被称为马尾和马尾灰，作为新型，高效且环保的天然温和催化剂。这些催化剂的结构通过FT-IR，XRF，SEM-EDS，N 2吸附-解吸，XRD和ICP分析等不同技术表征。从分析中获得的结果表明，马尾和马尾灰都可以充当固体酸催化剂。另外，进一步的详细分析表明它们具有不同的表面积，孔隙率和晶体结构，这会影响它们的催化活性。的2-氨基-4-合成ħ-二苯甲基衍生物是通过一锅三组分的二甲酮，丙二腈和各种芳族醛缩合来进行的，以比较它们在无溶剂条件下的催化活性。由于其高孔隙率和高表面积，与马尾本身相比，马尾灰产生更好的结果。FT-IR，质量，1 H-NMR和13 C-NMR光谱用于鉴定本研究中的合成化合物。该方法的一个重要优点是使用了这些有效的天然催化体系，这些体系具有低成本，温和的反应条件，无毒和可重复使用等特点，从而可以以高至极
• Synthesis of Fe3O4 Nanoparticles Bound with Polyethylene Glycol Substituted 1-Methyl Imidazolium Bromide and Their Application as Nanomagnetic and Recyclable Phase-transfer Catalysts for the Green and Efficient Synthesis of 4H-pyrans
  作者：Faranak Najafi、Mehdi Fallah-Mehrjardi

  DOI：10.2174/1570178615666180126155640

  日期：2018.7.26

  Immobilization of polyethylene glycol substituted 1-methylimidazolium bromide on the surface of Fe3O4 magnetic nanoparticles led to the synthesis of powerful and recyclable heterogeneous phase-transfer catalysts which were successfully used for the one-pot three-component condensation of aryl aldehydes, malononitrile and 1,3-dicarbonyl compounds, to afford the corresponding 2-amino-3- cyano-4H-pyrans. The catalysts can be readily recovered by simple magnetic decantation, and they can be reused several times with no considerable loss in their activity.

  将聚乙二醇取代的 1-甲基溴化咪唑鎓固定在 Fe3O4 磁性纳米粒子表面，合成了功能强大且可回收的异相转移催化剂，并成功用于芳基醛、丙二腈和 1,3-二羰基化合物的一锅三组分缩合反应，得到相应的 2-氨基-3-氰基-4H-吡喃。通过简单的磁性倾析，催化剂就可以很容易地回收，而且可以重复使用多次，其活性也不会有太大的损失。
• Mobinikhaledi, Akbar; Jabbarpour, Mahsa, Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 4, p. 1211 - 1218
  作者：Mobinikhaledi, Akbar、Jabbarpour, Mahsa

  DOI：——

  日期：——
• Screening of a library of 4-aryl/heteroaryl-4H-fused pyrans for xanthine oxidase inhibition: synthesis, biological evaluation and docking studies
  作者：Ramandeep Kaur、Fatima Naaz、Sahil Sharma、Samir Mehndiratta、Manish Kumar Gupta、Preet Mohinder Singh Bedi、Kunal Nepali

  DOI：10.1007/s00044-015-1382-0

  日期：2015.8

  A series of 4-aryl/heteroaryl-4H-fused pyrans was synthesized via multicomponent reaction in a microwave synthesizer. All the pyrans were evaluated for in vitro xanthine oxidase inhibition. Structure-activity relationship was also established. Among the series of 108 compounds, Compound 5n was the most potent displaying remarkable inhibition against the enzyme with an IC50 value of 0.59 mu M. Enzyme kinetic study was carried out for the compound 5n to determine the type of inhibition. The study revealed that the compound 5n was a mixed-type inhibitor. Molecular modelling studies were also performed to figure out the interactions of both the enantiomers of 5n with the amino acid residues of the enzyme.[GRAPHICS].