2-amino-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile | 74873-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile
• CAS: 74873-47-5
• 化学式: C₁₈H₁₉N₃O
• mdl: MFCD00585556
• 分子量: 293.368
• InChiKey: KUUFWDPZIKWPIK-UHFFFAOYSA-N

物化性质

• 熔点：
  226-227 °C(Solv: tetrahydrofuran (109-99-9))
• 沸点：
  514.4±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4-甲氧基苄烯)丙二腈 、 环庚酮 在 ammonium acetate 作用下， 以 苯 为溶剂， 反应 3.0h， 以68%的产率得到2-amino-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile
  参考文献：
  名称：

  A Simple Method for the Preparation of 2-Amino-4-aryl-3-cyanopyridines by the Condensation of Malononitrile with Aromatic Aldehydes and Alkyl Ketones in the Presence of Ammonium Acetate

  摘要：

  DOI：

  10.1055/s-1980-29021

文献信息

• An efficient protocol for the one-pot multicomponent synthesis of polysubstituted pyridines by using a biopolymer-based magnetic nanocomposite
  作者：Ali Maleki、Abbas Ali Jafari、Somayeh Yousefi、Vahid Eskandarpour

  DOI：10.1016/j.crci.2015.09.002

  日期：2015.12

  Résumé A biopolymer cellulose-based magnetic composite nanocatalyst was prepared and characterized by using scanning electron microscopy (SEM) and energy dispersive X-ray spectroscopy (EDX). Then, it was used efficiently in the multicomponent synthesis of polysubstituted pyridines under mild reaction conditions and using an easy work-up procedure at room temperature in ethanol. The nanocatalyst can be recovered easily and reused several times without significant loss of catalytic activity. Supplementary Materials: Supplementary materials for this article are supplied as separate files: mmc1.doc mmc2.zip mmc3.doc mmc4.doc

  摘要 基于生物聚合物纤维素的磁性复合纳米催化剂通过扫描电子显微镜（SEM）和能量色散X射线光谱（EDX）制备和表征。随后，该催化剂在温和反应条件下，以乙醇为溶剂并在室温下，高效用于多组分合成多取代吡啶。纳米催化剂易于回收，并可重复使用多次而不会显著损失催化活性。 补充材料： 本文的补充材料以单独文件形式提供： mmc1.doc mmc2.zip mmc3.doc mmc4.doc
• Poly N,N-dimethylaniline-formaldehyde supported on silica-coated magnetic nanoparticles: a novel and retrievable catalyst for green synthesis of 2-amino-3-cyanopyridines
  作者：Sajad Asadbegi、Mohammad Ali Bodaghifard、Akbar Mobinikhaledi

  DOI：10.1007/s11164-017-3200-4

  日期：2020.3

  Preparation and application of novel and reusable magnetic nanoparticles with poly N,N-dimethylaniline-formaldehyde support as a heterogeneous basic catalyst have been described. The reported catalyst was characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, X-ray diffraction patterns, transmission electron microscopy, energy dispersive X-ray spectroscopy, thermogravimetric

  已经描述了具有聚N，N-二甲基苯胺-甲醛载体作为非均相碱性催化剂的新颖且可重复使用的磁性纳米粒子的制备和应用。所报道的催化剂通过傅里叶变换红外光谱，扫描电子显微镜，X射线衍射图，透射电子显微镜，能量色散X射线光谱，热重分析和振动样品磁力分析进行了表征。已经研究了这种有机-无机杂化纳米材料通过一锅四组分反应绿色合成2-氨基-3-氰基吡啶衍生物的催化性能。与以前的方法相比，这种新方法的优点是环保，反应时间短，产率高和后处理步骤容易。
• Zinc-catalyzed multicomponent reactions: Facile synthesis of fully substituted pyridines
  作者：Ramaiah Konakanchi、Shravankumar Kankala、Laxma Reddy Kotha

  DOI：10.1080/00397911.2018.1463545

  日期：2018.7.18

  Abstract A first example of environmentally benign zinc complex catalyzed one-pot four-component reaction between malononitrile, ketone, ammonium acetate and aromatic aldehyde for the facile synthesis of fully substituted pyridines just within 2 min in environmentally friendly solvent ethanol has been optimized. GRAPHICAL ABSTRACT

  摘要 优化了环保型锌配合物催化丙二腈、酮、乙酸铵和芳香醛之间的一锅四组分反应，在环保溶剂乙醇中在 2 分钟内轻松合成全取代吡啶的第一个例子。图形概要
• Iodine‐catalyzed ultrasound‐assisted construction of pyridines and their glutamine synthetase molecular docking
  作者：Ramakanth Pagadala、Venkatesan Kasi、Shyam Perugu

  DOI：10.1002/jccs.201900389

  日期：2020.7

  Iodine‐promoted facile protocol is designed for the production of pyridines at room temperature under ultrasound irradiation. Eleven pyridine derivatives in excellent yields (91–97%) are synthesized with 2 hr reaction time. Additional advantage of the proposed ultrasound‐assisted eco‐friendly, cost‐effective protocol is easy separation of product, and our in silico studies show good binding affinity

  碘促进的操作规程旨在用于在室温下超声辐射下生产吡啶。在2小时的反应时间内可以合成11种吡啶衍生物，产率很高（91–97％）。拟议的超声辅助的生态友好，经济高效的方案的另一个优势是易于分离产品，我们的计算机研究表明对结合具有良好的结合亲和力，并具有很强的氢相互作用。
• SO₄⁻²/SnO₂–catalyzed cyclocondensation for the synthesis of fully functionalized pyridines
  作者：Ramesh Goud Koduri、Ramakanth Pagadala、Sathyanarayana Boodida、Ravi Varala

  DOI：10.1002/jhet.3806

  日期：2020.2

  An efficient and promising synthetic approach to assemble skeletons of multifunctionalized pyridine derivatives in presence of recyclable heterogeneous sulfated tin oxide (STO) catalyst has been evolved. The STO catalyst was used as a promoter for the cyclocondensation process in ethanol at 70°C. Overall performance of this catalyst was attributed to the cooperative contribution of its Lewis and Brønsted‐Lowry

  已经开发出一种有效且有前途的合成方法，用于在可回收的异质硫酸盐氧化锡（STO）催化剂存在下组装多官能吡啶衍生物的骨架。将STO催化剂用作70°C乙醇中环缩过程的促进剂。该催化剂的整体性能归因于其Lewis和Brønsted-Lowry酸性位点的协同作用。纳米STO催化剂是通过溶胶-凝胶法合成的，并通过傅里叶变换红外（FTIR）光谱，X射线衍射（XRD），1表征H-NMR和扫描电子显微镜（SEM）。该催化剂可耐受大多数底物，实验方案显示出宝贵的能力，包括高收率，操作简便，反应时间短和环境友好。新合成的非均相催化剂易于分离和重复使用。所有反应均在随后的循环中进行，而催化活性没有明显损失，并且熟练度很高。