2-amino-7,7-dimethyl-4-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-7,7-dimethyl-4-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-7,7-dimethyl-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-7,7-dimethyl-4-naphthalen-1-yl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: QCGHSHZXEYSVDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-7,7-dimethyl-4-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 在 碘苯二乙酸 作用下， 以 三氟乙酸 为溶剂， 反应 0.5h， 以78%的产率得到C₂₂H₁₇NO₃
  参考文献：
  名称：

  高价碘促进 4H-色烯转化为二氢呋喃和 2H-色烯

  摘要：

  摘要 在环境温度下通过一锅反应完成了在高价碘的作用下将 4H-色烯合成转化为二氢呋喃 (3) 和 2H-色烯 (11) 的新方案。二氢呋喃仅在碱性反应条件下形成，而 2H-色烯是在酸性条件下的产物。具有广泛的底物范围（包括各种杂环和高产率）的简单反应条件是该协议的吸引人的特点。图形概要

  DOI：

  10.1080/00397911.2020.1799013
• 作为产物：
  描述：

  2-(萘-1-基亚甲基)丙二腈 、 5,5-二甲基-1,3-环己二酮 在 吗啉 作用下， 以 乙醇 为溶剂， 以92%的产率得到2-amino-7,7-dimethyl-4-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  2-Amino-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile and 2-amino-7,7-dimethyl-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

  摘要：

  Syntheses and X-ray structural investigations have been carried out for the two title compounds, C20H16N2O2, (IIIa), and C22H20N2O2, (IIIb). In (IIIa), the heterocyclic ring adopts a sofa conformation, while in (IIIb), the ring has a flattened boat conformation. In both molecules, the fused cyclohexenone ring adopts a sofa conformation. The dihedral angles between these two at fragments are 3.5 (2) and 17.5 (2)degrees in (IIIa) and (IIIb), respectively. The dihedral angles between the pseudo-axial naphthalene substituents and the planes of the pyran rings are 90.9 (1) and 96.7 (1)degrees, respectively. In the crystal structure of (IIIa), intermolecular N-H...N and N-H...O hydrogen bonds link the molecules into infinite tapes along the b axis, while molecules of (IIIb) form centrosymmetric dimers via N-H...N hydrogen bonds, with only one H atom of the NH2 donor group taking part in hydrogen bonding.

  DOI：

  10.1107/s0108270104006924

文献信息

• 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。
• 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。
• 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）。
• A simple synthesis of magnetic nanoparticles-supported 4-aminomethylbenzoic acid as a highly efficient and reusable catalyst for synthesis of 2-amino-4H-chromene derivatives
  作者：Mohammad Mehdi Khodaei、Abdolhamid Alizadeh、Maryam Haghipour

  DOI：10.1007/s11164-017-3008-2

  日期：2020.2

  nanoparticles as a hybrid heterogeneous catalyst was synthesised and characterized by FT-IR, XRD, TGA, TEM, SEM and VSM techniques. The catalytic activity of this nanocatalyst was probed through one-pot synthesis of 2-amino-4H-chromene derivatives from three component reactions of various aldehydes, malononitrile and dimedone. The chemically and thermally stable catalyst was easily recovered using an external

  合成了一种新型的4-氨基甲基苯甲酸官能化的Fe 3 O 4磁性纳米颗粒作为杂相多相催化剂，并通过FT-IR，XRD，TGA，TEM，SEM和VSM技术对其进行了表征。该纳米催化剂的催化活性是通过一锅合成2-氨基-4 H-色烯衍生物来探测的，该衍生物由各种醛，丙二腈和二甲酮的三个组分反应组成。化学和热稳定的催化剂很容易使用外部磁体进行回收，并至少连续五次重复使用，而活性没有明显损失。该方法的另一优点是方法简单，产物产率高，反应条件温和和反应时间短。
• Effect of Substituents on the Crystal Structures, Optical Properties, and Catalytic Activity of Homoleptic Zn(II) and Cd(II) β-oxodithioester Complexes
  作者：Chote Lal Yadav、Anamika、Gunjan Rajput、Kamlesh Kumar、Michael G. B. Drew、Nanhai Singh

  DOI：10.1021/acs.inorgchem.0c01195

  日期：2020.8.17

  Five novel zinc(II) and cadmium(II) β-oxodithioester complexes, [Zn(L1)2] (1), [Zn(L2)2]n (2), [Zn(L3)2]n (3) [Cd(L1)2]n (4), [Cd(L2)2]n (5), with β-oxodithioester ligands, where L1 = 3-(methylthio)-1-(thiophen-2-yl)-3-thioxoprop-1-en-1-olate, L2 = 3-(methylthio)-1-(pyridin-3-yl)-3-thioxoprop-1-en-1-olate, and L3 = 3-(methylthio)-1-(pyridin-4-yl)-3-thioxoprop-1-en-1-olate, were synthesized and characterized

  五个新颖的锌（II）和镉（II）β-氧二硫酯配合物[Zn（L1）2 ]（1），[Zn（L2）2 ] n（2），[Zn（L3）2 ] n（3） [Cd（L1）2 ] n（4），[Cd（L2）2 ] n（5），具有β-氧二硫酯配体，其中L1 = 3-（甲硫基）-1-（噻吩-2-基）-3 -thioxoprop-1-en-1-olate，L2= 3-（甲硫基）-1-（吡啶-3-基）-3-硫代丙-1--1-烯酸酯，L3 = 3-（甲硫基）-1-（吡啶-4-基）-3-合成并通过元素分析，IR，UV-vis和NMR光谱（1 H和13 C 1 H}）对thioxoprop-1-en-1-olate进行了表征。所有配合物的固态结构通过单晶X射线晶体学确定。的β-oxodithioester配体键合至的Zn（II）/镉（II）中的O的金属离子∧ S和N的螯合剂/螯合剂桥接方式导致1D的形成（在2 - 4