2‑amino‑4‑(3‑methoxyphenyl)‑7,7‑dimethyl‑5‑oxo‑5,6,7,8‑tetrahydro‑4H‑chromene‑3‑carbonitrile | 302344-63-4

• 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‑(3‑methoxyphenyl)‑7,7‑dimethyl‑5‑oxo‑5,6,7,8‑tetrahydro‑4H‑chromene‑3‑carbonitrile
• 英文别名: 2-amino-4-(3-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-5,6,7,8-tetrahydro-4-(3-methoxyphenyl)-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile；2-amino-7,7-dimethyl-4-(3-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-3-cyano-4-(3-methoxyphenyl)-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran；2-amino-4-(3-methoxyphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran；2-amino-3-cyano-7,7-dimethyl-4-(3-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-1-benzopyran；2-amino-4-(3-methoxyphenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• CAS: 302344-63-4
• 化学式: C₁₉H₂₀N₂O₃
• 分子量: 324.379
• InChiKey: CBMJBNCXWAAMBS-UHFFFAOYSA-N

物化性质

• 熔点：
  188-190 °C(Solv: ethanol (64-17-5))
• 沸点：
  557.5±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

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‑(3‑methoxyphenyl)‑7,7‑dimethyl‑5‑oxo‑5,6,7,8‑tetrahydro‑4H‑chromene‑3‑carbonitrile 、 环己酮 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 以96%的产率得到11-Amino-12-(3-methoxy-phenyl)-3,3-dimethyl-2,3,4,7,8,9,10,12-octahydro-5-oxa-6-aza-naphthacen-1-one
  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
• 作为产物：
  描述：

  3-甲氧基苯甲醛 在 哌啶 作用下， 以 甲醇 为溶剂， 生成 2‑amino‑4‑(3‑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

• Ionic liquids containing plant derived benzoate as anions, exhibiting supramolecular polymeric aggregation: Impact of the aggregation on organic catalysis in aqueous medium
  作者：Muhammad Naveed Javed、Imran Ali Hashmi、Shoaib Muhammad、Ahmed Bari、Syed Ghulam Musharraf、Syed Junaid Mahmood、Saima Javed、Firdous Imran Ali、Faisal Rafique、Muhammad Amjad Ilyas、Waqas Ahmed Waseem

  DOI：10.1016/j.molliq.2021.116329

  日期：2021.8

  The supramolecular polymeric aggregation behaviour of these ILs has been studied through high-resolution electron spray ionization mass spectrometry (HR-ESI-MS). Furthermore, these ILs were applied as catalyst/phase transfer catalyst in the synthesis of tetrahydrobenzo[b]pyran and its derivatives. These reactions were conducted in aqueous medium under ultrasound assistance. The results suggested that

  天然存在的苯甲酸 （BA） 衍生阴离子已被用于制备无卤素亲水性离子液体 （ILs 1-4）。这些 IL 的超分子聚合物聚集行为已通过高分辨率电子喷雾电离质谱 （HR-ESI-MS） 进行了研究。此外，这些 ILs 被用作催化剂/相转移催化剂合成四氢苯并[b]吡喃及其衍生物。这些反应在超声辅助下在水性介质中进行。结果表明，1-乙基-3-甲基咪唑鎓 2-羟基苯甲酸酯 （IL-1） 是一种高效的催化剂，在 30 分钟内产生 86.9% 的产物。此外，还研究了 ILs 的聚集行为对其催化活性的影响。
• One-pot synthesis of 2-amino-3-cyano-4<i>H</i>-pyrans and pyran-annulated heterocycles using sodium citrate as an organo-salt based catalyst in aqueous ethanol
  作者：Aiborlang Thongni、Pynskhemborlang T. Phanrang、Arup Dutta、Rishanlang Nongkhlaw

  DOI：10.1080/00397911.2021.1998535

  日期：2022.1.2

  shorter reaction time, utilization of eco-friendly solvents, operational simplicity, mild reaction conditions, and maximum product yield. Moreover, the use of sodium citrate as an easily available, cheap and benign catalyst plays a pivotal role from a green perspective, considering its high recyclability and easy recovery. Therefore, this present methodology offers numerous possibilities in terms of large-scale

  摘要 柠檬酸钠作为一种高效催化剂被开发用于合成官能化的 2-氨基-3-氰基-4 H-吡喃和吡喃环化杂环。该方法涉及芳香醛、丙二腈和 1,3-二羰基化合物与 EtOH 的一锅三组分反应：H 2O (1:1 v/v) 在室温下作为溶剂。该协议具有几个优点，例如更短的反应时间、环保溶剂的利用、操作简单、反应条件温和和产品收率最高。此外，考虑到柠檬酸钠的高可回收性和易回收性，从绿色角度来看，柠檬酸钠作为一种易于获得、廉价和良性的催化剂发挥着关键作用。因此，本方法在大规模工业合成或应用于众多有机转化方面提供了许多可能性。此外，还对产物4aa形成的机理途径进行了理论研究，以确定柠檬酸钠对DFT法反应可行性的催化作用，使用B3LYP泛函。
• 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。
• Nano α-Al₂O₃supported ammonium dihydrogen phosphate (NH₄H₂PO₄/Al₂O₃): preparation, characterization and its application as a novel and heterogeneous catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives
  作者：Behrooz Maleki、Samaneh Sedigh Ashrafi

  DOI：10.1039/c4ra07813f

  日期：——

  8-tetrahydrobenzo[b]pyrans and 6-amino-5-cyano-4-aryl-1,4-dihydropyrano[2,3-c]pyrazoles from the condensation of various aldehydes, malononitrile, and 1,3-dicarbonyl compounds (1,3-cyclohexanedione or 5,5-dimethyl-1,3-cyclohexanedione) or 3-methyl-1-phenyl-2-pyrazoline-5-one, using NH4H2PO4/Al2O3 with good yields. The use of easily available catalyst, shorter reaction times, better yields, the simplicity of the reaction

  为制备2-氨基-3-氰基-4-芳基-7,7-二甲基-5,6,7,8-四氢苯并[ b ]吡喃和6-氨基的简单，有效和环境友好的方法被开发出来。来自各种醛，丙二腈和1,3-二羰基化合物（1,3-环己二酮或5,5-二甲基）缩合的-5-氰基-4-芳基-1,4-二氢吡喃并[2,3- c ]吡唑-1,3-环己二酮）或3-甲基-1-苯基-2-吡唑啉-5-酮，使用NH 4 H 2 PO 4 / Al 2 O 3产量高。使用容易获得的催化剂，更短的反应时间，更好的产率，反应的简单性，非均相系统和容易的后处理是本方法的优点。催化剂的表征是通过FT-IR光谱，X射线衍射（XRD）技术，热分析（TG / DTG）和透射电子显微镜（TEM）进行的。
• Facile pathway for synthesis of two efficient catalysts for preparation of 2-aminothiophenes and tetrahydrobenzo[b]pyrans
  作者：Hamid Reza Saadati-Moshtaghin、Farrokhzad Mohammadi Zonoz

  DOI：10.1007/s11164-017-3223-x

  日期：2018.3

  exhibited the excellent catalytic efficiency in condensation reaction for the preparation of tetrahydrobenzo[b]pyrans under solvent-free conditions as well as in the synthesis of 2-aminothiophenes via Gewald reaction. It must be noted that, HPA supported magnetite nanoparticles catalyzed the preparation of tetrahydrobenzo[b]pyrans, whereas for Gewald reaction amine-functionalized magnetite nanoparticles acted

  摘要 我们在此报告了一种新型的可磁循环催化剂，该催化剂由接枝在改性的Fe 3 O 4上的铁取代的Keggin型杂多酸（HPA）组成纳米粒子。合成的杂化纳米材料在无溶剂条件下制备四氢苯并[b]吡喃的缩合反应以及通过Gewald反应合成2-氨基噻吩中均具有优异的催化效率。必须注意的是，HPA负载的磁铁矿纳米颗粒催化了四氢苯并[b]吡喃的制备，而对于Gewald反应，胺官能化的磁铁矿纳米颗粒充当了催化剂。使用不同的表征技术，例如傅立叶变换红外（FT-IR），X射线粉末衍射（XRD），场发射扫描电子显微镜（FESEM），透射电子显微镜（TEM）和振动样品磁力计（VSM）来表征。杂化纳米材料。通过连续运行五次来确认催化剂的可重复使用性。将制得的催化剂的性能与先前报道的各种催化剂进行了比较。发现新合成的催化剂在反应时间，产率和催化剂分离容易性方面是最有效的。 图形概要