Ethyl-2,7,7-trimethyl-4-(2-hydroxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 1360454-84-7

• 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: Ethyl-2,7,7-trimethyl-4-(2-hydroxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: ethyl 4-(2-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；Ethyl 4-(2-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 1360454-84-7
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: NEVDZBZLCADEPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 水杨醛 、 5,5-二甲基-1,3-环己二酮 在 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以90%的产率得到Ethyl-2,7,7-trimethyl-4-(2-hydroxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis and application of novel urea–benzoic acid functionalized magnetic nanoparticles for the synthesis of 2,3-disubstituted thiazolidin-4-ones and hexahydroquinolines

  摘要：

  使用Fe3O4@SiO@(CH2)3-尿素-苯甲酸作为催化剂制备六氢喹啉和2,3-二取代噻唑啉-4-酮。

  DOI：

  10.1039/d2ra02205b

文献信息

• Catalyst-free efficient synthesis of polyhydroquinolines using polyethylene glycol as a solvent and evaluation of their cytotoxicity
  作者：Humani Paidepala、Siddavatam Nagendra、Venkateswarlu Saddanappu、Anthony Addlagatta、Biswanath Das

  DOI：10.1007/s00044-013-0706-1

  日期：2014.2

  AbstractAn eco-friendly one-pot synthesis of polyhydroquinolines by four-component coupling of aldehydes, dimedone, ethylacetoacetate, and ammonium acetate using polyethylene glycol as a solvent at room temperature has been accomplished. The conversion was complete within 2–4 h, and the products were formed in high yields (83–95 %). No any additional catalyst was required. Several known and unknown

  摘要在室温下，以聚乙二醇为溶剂，通过醛，二甲酮，乙酸乙酯和乙酸铵的四组分偶联，实现了环保的一锅法合成多氢喹啉。转换在2-4小时内完成，并且形成的产品收率很高（83-95％）。不需要任何额外的催化剂。已经制备了几种已知和未知的聚氢喹啉。一些化合物表现出令人印象深刻的细胞毒性活性。 图形概要已经开发了聚氢喹啉衍生物的新的多组分合成。一些化合物的细胞毒活性令人印象深刻。
• Novel SO₃H-Functionalized Ionic Liquids - Catalyzed Facile and Efficient Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation under Ultrasound Irradiation
  作者：Bai Lin Li、Ai Guo Zhong、An Guo Ying

  DOI：10.1002/jhet.2070

  日期：2015.3

  A facile and efficient synthesis of polyhydroquinolines has been developed via four‐component condensation reactions of aldehydes, dimedone, ethyl acetoacetate, and ammonium acetate in the presence of Novel SO3H‐functionalized ionic liquid catalysts through Hantzsch reaction under ultrasound irradiation without solvent. Simple work‐up procedure, environmentally friendly, inexpensive, and non‐toxic

  在新型SO 3 H官能化离子液体催化剂存在下，通过Hantzsch反应，在无溶剂的情况下，通过Hantzsch反应，通过醛，二甲酮，乙酰乙酸乙酯和乙酸铵的四组分缩合反应，开发了一种简便高效的聚氢喹啉合成方法。该实用方法的重要特点是操作步骤简单，环保，廉价且无毒的催化剂，较短的反应时间以及优异的产品收率。
• One-pot synthesis and evaluation of anticancer activity of polyhydroquinoline derivatives catalyzed by [Msim]Cl
  作者：S. C. Jadhvar、H. M. Kasraliker、S. V. Goswami、A. V. Chakrawar、S. R. Bhusare

  DOI：10.1007/s11164-017-3069-2

  日期：2017.12

  bioactive polyhydroquinoline derivatives was developed via condensation of substituted salicylaldehyde, dimedone, ethyl acetoacetate and ammonium acetate catalyzed by 3-methyl-1-sulfonic acid imidazolium chloride ([Msim]Cl) in excellent yield. All synthesized derivatives were evaluated for inhibition of cancer cells. The initial assays reveals that some of the synthesized derivatives show significantly satisfactory

  通过3-甲基-1-磺酸咪唑鎓氯化物（[Msim] Cl）催化的取代水杨醛，二甲酮，乙酰乙酸乙酯和乙酸铵的缩合反应，开发了一种有效合成生物活性多氢喹啉衍生物的绿色方案，收率很高。评价所有合成的衍生物对癌细胞的抑制。初步分析显示，与对照（阿霉素）相比，某些合成衍生物对人乳腺癌细胞（MCF7）显示出显着令人满意的抑制活性，后者可能被开发为潜在抗癌药的新型铅支架。
• Copper nanoparticles grafted on carbon microspheres as novel heterogeneous catalysts and their application for the reduction of nitrophenol and one-pot multicomponent synthesis of hexahydroquinolines
  作者：Tibor Pasinszki、Melinda Krebsz、Győző György Lajgut、Tünde Kocsis、László Kótai、Sushama Kauthale、Sunil Tekale、Rajendra Pawar

  DOI：10.1039/c7nj03562d

  日期：——

  Novel carbon microsphere-supported metallic copper nanoparticles (Cu-NP/C) were synthesized using a low-cost and facile method based on carbonising a styrene-based, chelate-forming cation exchange resin loaded with Cu2+ ions. The metal–organic framework served as both copper and carbon source. Cu-NP/C microspheres were characterized by XRD, Raman, SEM, TGA, EDAX, and BET surface area analyser and were

  基于碳化和负载铜2+离子的苯乙烯基螯合形成阳离子交换树脂的碳化，使用低成本和简便的方法合成了新型碳微球负载的金属铜纳米颗粒（Cu-NP / C）。金属有机框架既是铜又是碳源。通过XRD，拉曼，SEM，TGA，EDAX和BET表面积分析仪对Cu-NP / C微球进行了表征，并用作多相催化剂将NaBH 4将4-硝基苯酚还原为4-氨基苯酚以及基于醛，二甲酮，乙酰乙酸乙酯和乙酸铵的一锅多组分反应合成具有药用价值的六氢喹啉衍生物。可持续且廉价的原料，相对容易的合成过程，催化效率以及易于分离和重用的Cu-NP / C微球为大规模应用打开了方便之门。
• Melamine supported on hydroxyapatite-encapsulated-γ-Fe2O3: a novel superparamagnetic recyclable basic nanocatalyst for the synthesis of 1,4-dihydropyridines and polyhydroquinolines
  作者：Sedighe Igder、Ali Reza Kiasat、Mohamad Reza Shushizadeh

  DOI：10.1007/s11164-014-1808-1

  日期：2015.10

  γ-Fe2O3@ HAp@Melamine as a magnetic powerful basic nanocatalyst was probed through one-pot synthesis of 1, 4-dihydropyridine and polyhydroquinoline derivatives through Hantzsch condensation reaction under solvent-free thermal conditions. The heterogeneous catalyst could be recovered easily by simple magnetic decantation and reused many times without significant loss of its catalytic activity.

  在本文中，羟基磷灰石包封的γ-Fe的制备和表征2个ö 3纳米颗粒的纳米复合材料三聚氰胺官能（γ-的Fe 2 ö 3 @磷灰石@三聚氰胺）被呈现。通过红外光谱，扫描电子显微镜，热重量分析，X射线衍射，振动样品磁力计和元素分析对所得纳米复合材料进行表征。的催化活性γ-的Fe 2 ö 3通过无溶剂热条件下的Hantzsch缩合反应，通过一锅法合成1，4-二氢吡啶和聚氢喹啉衍生物，探索了HAp @ Melamine作为强磁性的碱性纳米催化剂。通过简单的磁倾析可以很容易地回收非均相催化剂，并且可以多次重复使用而又不会明显丧失其催化活性。