2-amino-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile | 164410-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-amino-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbontirile；2-amino-5,6,7,8-tetrahydro-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile；2-amino-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4-(2-methoxyphenyl)-4H-chromene-3-carbonitrile；2-amino-3-cyano-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydro-benzo[b]-pyran；2-amino-3-cyano-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran；2-amino-4-(2-methoxyphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran；2-amino-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• CAS: 164410-71-3
• 化学式: C₁₉H₂₀N₂O₃
• 分子量: 324.379
• InChiKey: DKIRZUDRSLZVFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 在 溶剂黄146 作用下， 反应 12.0h， 生成 4-(4-fluorophenylamino)-5-(2-methoxyphenyl)-8,8-dimethyl-8,9-dihydro-5H-chromeno[2,3-d]pyrimidin-6(7H)-one
  参考文献：
  名称：

  新型Chromeno [2,3-d]嘧啶-设计，合成和抗氧化活性

  摘要：

  简介：合理设计并合成了十四种新颖的8,8-二甲基-8,9-二氢-5H-铬[2,3-d]嘧啶-6（7H）-衍生物。用于靶分子的合成程序通过简便的方案完成，收率良好至优异（> 80％）。 方法：通过1H NMR，13C NMR，HR-MS和FT-IR光谱分析对所有合成的化合物进行表征。使用DPPH，ABTS，NO和H2O2方法评估了所有新化合物的体外抗氧化活性。 结果：在所有四种测试方法中，新型衍生物中，两种合成的化合物均表现出与抗坏血酸相似的良好抗氧化活性。

  DOI：

  10.2174/1570180814666161123143637
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 哌啶 作用下， 以 甲醇 为溶剂， 生成 2-amino-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  New multipotent tetracyclic tacrines with neuroprotective activity

  摘要：

  The synthesis and the biological evaluation (neuroprotection, voltage dependent calcium channel blockade, AChE/ BuChE inhibitory activity and propidium binding) of new multipotent tetracyclic tacrine analogues (5-13) are described. Compounds 7, 8 and 11 showed a significant neuroprotective effect on neuroblastoma cells subjected to Ca2+ overload or free radical induced toxicity. These compounds are modest AChE inhibitors [the best inhibitor (11) is 50-fold less potent than tacrine], but proved to be very selective, as for most of them no BuChE inhibition was observed. In addition, the propidium. displacement experiments showed that these compounds bind AChE to the peripheral anionic site (PAS) of AChE and, consequently, are potential agents that can prevent the aggregation of P-amyloid. Overall, compound 8 is a modest and selective AChE inhibitor, but an efficient neuroprotective agent against 70 mM K+ and 60 mu M H2O2. Based on these results, some of these molecules can be considered as lead candidates for the further development of anti-Alzheimer drugs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.025

文献信息

• 2-Hydroxyethyl-1-ammonium 3-hydroxypropane-1-sulfonate: a biodegradable and recyclable ionic liquid for the one-pot synthesis of 2-amino-3-cyano-4H-pyrans
  作者：Moones Honarmand、Andromachi Tzani、Anastasia Detsi

  DOI：10.1007/s13738-018-1537-2

  日期：2019.3

  2-Hydroxyethyl-1-ammonium 3-hydroxypropane-1-sulfonate ‘HAHS’ was synthesized as a novel ionic liquid and characterized by various techniques. ‘HAHS’ ionic liquid was efficiently applied as a multifunctional promoter for the three-component synthesis of 2-amino-3-cyano-4H-pyrans. The 2-amino-3-cyano-4H-pyrans were produced not only in high to excellent yields but also no toxic solvent or catalyst was used. ‘HAHS’ ionic liquid was recovered and reused four times without the considerable decreasing in its activity. The effect of hydroxyl groups in the structure of ‘HAHS’ ionic liquid on its catalytic activity was studied. Moreover, the biodegradability potential of the ionic liquid was examined using the 5-day biological oxygen demand closed bottle test and the results showed that ‘HAHS’ has remarkable biodegradability potential.

  2-羟乙基-1-铵-3-羟基丙烷-1-磺酸盐（HAHS）作为一种新型离子液体被合成，并通过多种技术手段进行了表征。HAHS离子液体被高效应用于2-氨基-3-氰基-4H-吡喃的三组分合成中，不仅产率从高到极佳，而且无需使用有毒溶剂或催化剂。HAHS离子液体可回收并重复使用四次，活性无显著下降。研究了HAHS离子液体结构中的羟基对其催化活性的影响。此外，通过5天生物需氧量闭瓶测试考察了该离子液体的生物降解潜力，结果显示HAHS具有显著的生物降解潜力。
• Introduction of organic/inorganic Fe₃O₄@MCM-41@Zr-piperazine magnetite nanocatalyst for the promotion of the synthesis of tetrahydro-4<i>H</i>-chromene and pyrano[2,3-<i>d</i>]pyrimidinone derivatives
  作者：Reyhaneh Pourhasan-Kisomi、Farhad Shirini、Mostafa Golshekan

  DOI：10.1002/aoc.4371

  日期：2018.7

  highly dispersed in the tetrahedral environment of silica framework and piperazine is successfully attached to the surface of the nanocatalyst in connection with zirconium. The prepared nanosized reagent (10–30 nm), shows excellent catalytic activity in the synthesis of tetrahydro‐4H‐chromene and pyrano[2,3‐d]pyrimidinone derivatives. All reactions are performed under mild and completely heterogeneous

  哌嗪修饰的Fe 3 O 4 @ MCM-41 @ Zr-MNPs易于制备，并使用傅里叶变换红外光谱（FT-IR），X射线粉末衍射（XRD），N 2吸附-解吸，透射电子显微镜进行表征（ TEM），能量色散X射线（EDX），振动样品磁力法（VSM）和热重分析（TGA）技术。表征结果表明，高度分散在二氧化硅骨架和哌嗪的四面体环境中的Zr可以成功地附着在与锆相关的纳米催化剂表面。制备的纳米级试剂（10–30 nm）在四氢-4 H-色烯和吡喃[2,3- d]嘧啶酮衍生物。所有反应均在温和且完全异质的反应条件下进行，且反应时间短。另一方面，由于其超顺磁性，该催化剂可通过施加外部磁场容易地分离并重复使用多次。
• Magnetic core–shell titanium dioxide nanoparticles as an efficient catalyst for domino Knoevenagel–Michael-cyclocondensation reaction of malononitrile, various aldehydes and dimedone
  作者：Ardeshir Khazaei、Fatemeh Gholami、Vahid Khakyzadeh、Ahmad Reza Moosavi-Zare、Javad Afsar

  DOI：10.1039/c4ra16300a

  日期：——

  Magnetic core–shell titanium dioxide nanoparticles (Fe3O4@SiO2@TiO2) were efficiently used for the preparation of tetrahydrobenzo[b]pyran derivatives via a one-pot three component condensation reaction of various aldehydes, dimedone and malononitrile at 100 °C under solvent-free conditions. The catalyst was synthesized and characterized by several techniques including X-ray diffraction (XRD), transmission

  磁性核-壳二氧化钛纳米颗粒（Fe 3 O 4 @SiO 2 @TiO 2）可通过各种浓度的醛，二甲酮和丙二腈的一锅三组分缩合反应有效地用于制备四氢苯并[ b ]吡喃衍生物。无溶剂条件下的℃。通过几种技术合成并表征了催化剂，包括X射线衍射（XRD），透射电子显微镜（TEM），场发射扫描电子显微镜（FESEM）和能量色散X射线光谱（EDX）。
• Introduction of taurine (2-aminoethanesulfonic acid) as a green bio-organic catalyst for the promotion of organic reactions under green conditions
  作者：Farhad Shirini、Nader Daneshvar

  DOI：10.1039/c6ra15432h

  日期：——

  derivatives are simply prepared via a three-component reaction in the presence of taurine as the catalyst. All these reactions are performed in water, a green solvent. The advantages of using of taurine as the catalyst are it is environmentally friendly, low cost, commercially available, easy to separate from the reaction mixture, and has high reusability. Use of this catalyst results in acceptable reaction

  牛磺酸（2-氨基乙烷磺酸）是存在于人体和许多其他生物中的半必需氨基酸，被用作绿色生物有机催化剂，以促进醛与丙二腈之间的Knoevenagel反应。同样，四酮也可以通过Knoevenagel反应生成，然后进行迈克尔加成反应。2-氨基-3-氰基-4 H-吡喃衍生物可通过以下方法简单地制备牛磺酸作为催化剂的三组分反应。所有这些反应均在绿色溶剂水中进行。使用牛磺酸作为催化剂的优点是环境友好，成本低廉，可商购，易于从反应混合物中分离并且具有高可重复使用性。使用这种催化剂可在不使用任何有机溶剂的情况下获得可接受的反应时间，高产率和高纯度的所得产物。
• Improvement in nanocomposite host (nanocavity of dealuminated zeolite Y)-guest (12-molybdophosphoric acid) catalytic activity and its application to the one-pot three-component synthesis of tetrahydrobenzo[ b ]pyrans
  作者：Seyedeh Fatemeh Hojati、Maryam Moosavifar、Toktam Ghorbanipoor

  DOI：10.1016/j.crci.2016.11.005

  日期：2017.5

  efficient chemoselective synthesis of tetrahydrobenzo[b]pyran derivatives, and the corresponding products were obtained in good to excellent yields in very short reaction times. Furthermore, the catalytic activity of this new catalyst in the synthesis of tetrahydrobenzo[b]pyrans was compared with MPA encapsulated in zeolite Y dealuminated by the hydrothermal method. The catalyst (MPA–MDAZY) was recovered

  摘要 采用化学方法（乙二胺四乙酸）对沸石 Y 进行脱铝，以修饰沸石结构，以负载 12-磷酸钼酸 (MPA)。MPA 封装在改性脱铝沸石 Y (MDAZY) 的纳米腔中，并通过傅里叶变换红外、X 射线衍射和原子吸收光谱进行表征。新催化剂用于四氢苯并[b]吡喃衍生物的高效化学选择性合成，并在很短的反应时间内以良好至极好的收率获得了相应的产物。此外，将这种新催化剂在四氢苯并[b]吡喃合成中的催化活性与包封在通过水热法脱铝的沸石Y中的MPA进行了比较。