2-amino-7,7-dimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile | 129354-39-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-amino-7,7-dimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
• 英文别名: 2-amino-3-cyano-7,7-dimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline；2-amino-4-phenyl-3-cyano-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline；2-amino-7,7-dimethyl-5-oxo-4-phenyl-1,4,6,8-tetrahydroquinoline-3-carbonitrile
• CAS: 129354-39-8
• 化学式: C₁₈H₁₉N₃O
• 分子量: 293.368
• InChiKey: VPCRUYGXFMZIQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-7,7-dimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile 在 sodium sulfide 、 盐酸 、 水 作用下， 以 甲醇 为溶剂， 以72%的产率得到2-amino-4-phenyl-7,7-dimethyl-5-thioxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  One Pot Synthesis of tetrahydroquinoline-5-thiones and Evaluation of their Antimicrobial Activities

  摘要：

  报告了各种四氢喹啉-5-亚硫酰的单锅合成。评估了所获产物对各类细菌的抗菌活性。

  DOI：

  10.3184/030823408x314473
• 作为产物：
  描述：

  2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以69%的产率得到2-amino-7,7-dimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  Elnagdi, Mohamed Hilmy; Aal, Fatma Abdel Maksoud Abdel; Yassin, Youssef Mahfouz, Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 6, p. 971 - 976

  摘要：

  DOI：

文献信息

• Nano-zirconia as an excellent nano support for immobilization of sulfonic acid: a new, efficient and highly recyclable heterogeneous solid acid nanocatalyst for multicomponent reactions
  作者：Ali Amoozadeh、Salman Rahmani、Mehrnoosh Bitaraf、Fatemeh Bolghan Abadi、Elham Tabrizian

  DOI：10.1039/c5nj02430g

  日期：——

  Nano-zirconia-supported sulfonic acid as a novel, highly efficient and recyclable heterogeneous nanocatalyst is reported for the synthesis of multicomponent reactions.

  报告了一种新型的、高效的、可回收的纳米催化剂——纳米氧化锆支撑的磺酸，用于合成多组分反应。

• Evaluation of magnetically recyclable nano-Fe3O4 as a green catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono and bis 1,4-dihydropyridine derivatives
  作者：Bagher Amirheidari、Mohammad Seifi、Mehdi Abaszadeh

  DOI：10.1007/s11164-015-2220-1

  日期：2016.4

  Magnetically separable Fe3O4 nanoparticles were used as an environmental friendly catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono- and bis-1,4-dihydropyridine derivatives via three-component reactions of aromatic aldehydes and malononitrile with cyclic β-dicarbonyls or cyclic β-enaminoketones respectively. These reactions were carried out in EtOH and at reflux. Fe3O4 nanoparticles can be magnetically separated from the reaction mixture by a magnet and recycled without significant loss of catalytic activity.

  磁性可分离的Fe3O4纳米颗粒被用作一种环保型催化剂，用于通过芳香醛、丙二腈与环状β-二羰基化合物或环状β-烯胺酮的三组分反应，合成单/双四氢-4H-色烯衍生物和单/双1,4-二氢吡啶衍生物。这些反应在乙醇中进行并回流。Fe3O4纳米颗粒可通过磁铁从反应混合物中磁性分离，并且可以回收利用而不会显著损失催化活性。
• Microwave-irradiated one-pot synthesis of quinoline derivatives catalyzed by triethylamine
  作者：Sanele Moloi、Suresh Maddila、Sreekantha B. Jonnalagadda

  DOI：10.1007/s11164-017-2986-4

  日期：2017.11

  Abstract An efficient and swift microwave (MW)-mediated procedure for synthesis of 11 quinoline derivatives has been designed based on reaction between aromatic aldehydes, malononitrile, 5,5-dimethylcyclohexane-1,3-dione, and ammonium acetate at room temperature in ethanol solvent. The main advantages of this method are operational simplicity, excellent yield (92–98 %), use of green solvent, short

  摘要 基于芳香醛，丙二腈，5,5-二甲基环己烷-1,3-二酮和乙酸铵在乙醇溶剂中室温下的反应，设计了一种高效且快速的微波介导合成11种喹啉衍生物的方法。该方法的主要优点是操作简便，产率高（92-98％），使用绿色溶剂，反应时间短（<15分钟），反应条件温和且无副产物。 图形概要
• Ammonium acetate as a catalyst and/or reactant in the reaction of dimedone, aromatic aldehyde, and malononitrile: synthesis of tetrahydrobenzo[b]pyrans and hexahydroquinolines
  作者：Adeleh Moshtaghi Zonouz、Somaieh Okhravi、Davood Moghani

  DOI：10.1007/s00706-016-1683-0

  日期：2016.10

  AbstractThe reaction of aromatic aldehydes, dimedone, and malononitrile in the presence of ammonium acetate has afforded tetrahydrobenzo[b]pyrans instead of polyhydroquinolines under both grinding and reflux conditions; thus ammonium acetate acts as a catalyst for this transformation instead of a reactant. Polyhydroquinoline derivatives were also synthesized via a one-pot condensation of aromatic aldehydes

  摘要在研磨和回流条件下，芳族醛，二甲酮和丙二腈在乙酸铵存在下的反应得到四氢苯并[ b ]吡喃，而不是聚氢喹啉。因此乙酸铵代替反应物充当该转化的催化剂。聚氢喹啉衍生物还可以通过芳族醛，丙二腈和烯胺酮的一锅缩合反应合成，该缩合反应是由二甲酮和乙酸铵在回流的乙醇中以高收率反应制备的。 图形概要
• Crown ether complex cation ionic liquids: synthesis and catalytic applications for the synthesis of tetrahydro-4<i>H</i>-chromene and 1,4-dihydropyridine derivatives
  作者：Mehdi Abaszadeh、Mohammad Seifi

  DOI：10.1080/17415993.2017.1293058

  日期：2017.7.4

  ABSTRACT A series of crown ether complex cation ionic liquids (CECILs) are synthesized by crown ethers chelated with sodium benzenesulfonates, and used as a green and environmental catalyst, for the synthesis of tetrahydro-4H-chromene and 1,4-dihydropyridine derivatives by three-component reactions of aromatic aldehydes and malononitrile with cyclic β-dicarbonyls or cyclic β-enaminoketones respectively

  摘要 冠醚与苯磺酸钠螯合合成了一系列冠醚络合阳离子离子液体（CECILs），作为一种绿色环保催化剂，用于三氢苯磺酸钠合成四氢-4H-色烯和1,4-二氢吡啶衍生物。 - 芳香醛和丙二腈分别与环状 β-二羰基或环状 β-烯氨基酮在 H2O/EtOH (1:1) 中在回流条件下的组分反应。CECILs作为一种绿色环保的催化剂，容易获得且稳定。此外，高转化率、短反应时间和更清洁的反应曲线是该方法的一些优点。图形概要