2-amino-4-(4-dimethylaminophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile | 329692-88-8

• 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-dimethylaminophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile
• 英文别名: 2-Amino-4-[4-(dimethylamino)phenyl]-5,6,7,8,9-pentahydrocyclohepta[1,2-b]pyrid ine-3-carbonitrile；2-amino-4-[4-(dimethylamino)phenyl]-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile
• CAS: 329692-88-8
• 化学式: C₁₉H₂₂N₄
• 分子量: 306.41
• InChiKey: OYYKOULLWBLMTE-UHFFFAOYSA-N

物化性质

• 沸点：
  531.6±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 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：
  65.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 丙二腈 、 环庚酮 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到2-amino-4-(4-dimethylaminophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile
  参考文献：
  名称：

  SO2-4 / SnO2催化的环缩合反应用于合成完全官能化的吡啶

  摘要：

  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。

  DOI：

  10.1002/jhet.3806

文献信息

• 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
• 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。
• Silver(<scp>i</scp>)–N-heterocyclic carbene catalyzed multicomponent reactions: a facile synthesis of multisubstituted pyridines
  作者：Shravankumar Kankala、Ramakanth Pagadala、Suresh Maddila、Chandra Sekhar Vasam、Sreekantha B. Jonnalagadda

  DOI：10.1039/c5ra16582b

  日期：——

  A room temperature four component reaction between aromatic aldehydes, CH₂(CN)₂and NH₄OAc with ketones mediated by Ag(i)–NHC pre-catalysts to produce multisubstituted pyridines in a short reaction time in eco-friendly ethanol was described.

  一种在室温下进行的四组分反应，涉及芳香醛、CH₂(CN)₂和NH₄OAc与酮在Ag(i)–NHC前催化剂介导下反应，以在环保乙醇中在短时间内产生多取代吡啶。
• An efficient method for the multicomponent synthesis of multisubstituted pyridines, a rapid procedure using Au/MgO as the catalyst
  作者：Ramakanth Pagadala、Suresh Maddila、Vashen Moodley、Werner E. van Zyl、Sreekantha B. Jonnalagadda

  DOI：10.1016/j.tetlet.2014.05.089

  日期：2014.7

  Au/MgO proved to be a highly efficient and reusable catalyst for multicomponent coupling reactions at 70 degrees C. The synthesized multisubstituted pyridines were obtained in high yields and in short reaction times. With facile work-up, the novel catalyst can be readily recovered after the reaction and reused without any loss of its catalytic activity. (C) 2014 Elsevier Ltd. All rights reserved.
• 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。