methyl 4-(2-methylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylate | 1437319-86-2

• 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: methyl 4-(2-methylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylate
• 英文别名: Methyl 2,7,7-trimethyl-4-(2-methylphenyl)-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate；methyl 2,7,7-trimethyl-4-(2-methylphenyl)-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 1437319-86-2
• 化学式: C₂₁H₂₅NO₃
• 分子量: 339.434
• InChiKey: OLAZKTCCRHMVGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 乙酰乙酸甲酯 、 2-甲基苯甲醛 在 ammonium acetate 作用下， 以 水 为溶剂， 反应 2.17h， 以91%的产率得到methyl 4-(2-methylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylate
  参考文献：
  名称：

  One-pot multicomponent synthesis hexahydroquinoline derivatives in Triton X-100 aqueous micellar media

  摘要：

  简述 在室温下，在水溶剂 Triton X-100 的存在下，通过醛、二甲基酮、乙酰乙酸甲酯和乙酸铵的四组分缩合反应，简便高效地合成了六氢喹啉衍生物 (5a-o)。在水溶剂中只需使用 20 摩尔 % 的 Triton X-100 即可。傅立叶变换红外光谱、19F NMR、1H NMR、13C NMR 光谱和元素分析证实了这些化合物的结构。

  DOI：

  10.1016/j.crci.2012.11.017

文献信息

• Basic isoreticular metal-organic framework (IRMOF-3) porous nanomaterial as a suitable and green catalyst for selective unsymmetrical Hantzsch coupling reaction
  作者：Sadegh Rostamnia、Hongchuan Xin

  DOI：10.1002/aoc.3136

  日期：2014.5

  A catalytic amount of the basic metal–organic framework (IRMOF‐3) with organic substrates was found to be an efficient, selective and waste‐free green approach for the unsymmetrical Hantzsch coupling reaction. The catalyst can be isolated from the reaction mixture and reused at least four times. Copyright © 2014 John Wiley & Sons, Ltd.

  发现催化量的带有有机底物的基本金属-有机骨架（IRMOF-3）是一种有效，选择性且无浪费的绿色方法，可用于不对称的Hantzsch偶联反应。可以从反应混合物中分离出催化剂，并重复使用至少四次。版权所有©2014 John Wiley＆Sons，Ltd.
• Ethylene diamine post-synthesis modification on open metal site Cr-MOF to access efficient bifunctional catalyst for the Hantzsch condensation reaction
  作者：Sadegh Rostamnia、Hassan Alamgholiloo、Maryam Jafari

  DOI：10.1002/aoc.4370

  日期：2018.8

  Ethylene diamine functionalized MIL‐101(Cr) was established to be an efficient organocatalyst for single‐pot synthesis of polyhydroquinolines via four‐component condensation reaction between aldehydes, dimedone, β‐ketoecters and ammonium acetate in aqueous medium. Ethylene diamine of the parent open metal site MIL‐101(Cr) has been carried out through a post‐synthetic modification (PSM) technique. Efficient

  乙二胺官能化的MIL-101（Cr）被确立为通过在水性介质中醛，二甲酮，β-酮缩酮和乙酸铵之间的四组分缩合反应来单锅合成多氢喹啉的有效有机催化剂。母体开放金属位点MIL-101（Cr）的乙二胺已通过合成后修饰（PSM）技术进行了研究。高效的转化，温和的条件，容易的产物分离以及有机催化剂的潜在高回收率是该协议的关键特征。
• Water dispersed magnetic nanoparticles (H2O-DMNPs) of γ-Fe2O3 for multicomponent coupling reactions: a green, single-pot technique for the synthesis of tetrahydro-4H-chromenes and hexahydroquinoline carboxylates
  作者：Sadegh Rostamnia、Ayat Nuri、Hongchuan Xin、Ali Pourjavadi、Seyed Hassan Hosseini

  DOI：10.1016/j.tetlet.2013.04.048

  日期：2013.6

  Water dispersed magnetic nanoparticles (DMNPs) of gamma-Fe2O3 represent a simple and green catalyst for the rapid three-component synthesis of tetrahydro-4H-chromene and hexahydroquinoline carboxylate skeletons via single-pot domino Knoevenagel-Michael-cyclization reactions. (C) 2013 Elsevier Ltd. All rights reserved.
• Brønsted acidic hydrogensulfate ionic liquid immobilized SBA-15: [MPIm][HSO4]@SBA-15 as an environmentally friendly, metal- and halogen-free recyclable catalyst for Knoevenagel–Michael-cyclization processes
  作者：Sadegh Rostamnia、Asadollah Hassankhani、Habib Golchin Hossieni、Behnam Gholipour、Hongchuan Xin

  DOI：10.1016/j.molcata.2014.09.017

  日期：2014.12

  The Bronsted acidic imidazolium-based metal-free and halogen-free ionic liquid hydrogen sulfate was immobilized on nanoporous silica SBA-15. The structures of synthesized catalysts were investigated using different characterization techniques, including FT-IR, small angle XRD, SEM, TEM and TGA. The [MPIm][HSO4]@SBA-15 is used as an alternative to conventional catalysts in the Knoevenagel-Michael-cyclization processes for the synthesis of tetrahydrochromenes and hexahydroquinoline carboxylates via a multicomponent procedure. The reaction time is reduced drastically and the reaction is progressed in an environmentally friendly way. The immobilized catalyst can be recycled without substantial loss of activity after seven runs. (C) 2014 Elsevier B.V. All rights reserved.
• Covalently Bonded Ionic Liquid-Type Sulfamic Acid onto SBA-15: SBA-15/NHSO3H as a Highly Active, Reusable, and Selective Green Catalyst for Solvent-Free Synthesis of Polyhydroquinolines and Dihydropyridines
  作者：Sadegh Rostamnia、Asadollah Hassankhani

  DOI：10.1055/s-0034-1379477

  日期：——

  Amine-functionalized ordered mesoporous organic-inorganic hybrid materials are designed as solid supports to covalently immobilize the SO3H group to achieve sulfamic acid (SBA-15/ NHSO3H) as a novel catalyst. SBA-15/NHSO3H as ionic liquid-type heterogeneous catalyst could be separated easily from reaction products and recycled, showing superiority over homogeneous catalysts.