Ethyl 4-(2,5-dimethylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 332409-43-5

• 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 4-(2,5-dimethylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: ethyl 4-(2,5-dimethylphenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 332409-43-5
• 化学式: C₂₃H₂₉NO₃
• 分子量: 367.488
• InChiKey: DSIVMOSQFGSTFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  2,5-二甲基苯甲醛 、 乙酰乙酸乙酯 、 5,5-二甲基-1,3-环己二酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以89%的产率得到Ethyl 4-(2,5-dimethylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  One-pot multi-component synthesis of polyhydroquinolines at ambient temperature

  摘要：

  摘要 描述了一种在室温下通过醛、1,3-二酮、β-酮酯和乙酸铵在乙醇介质中进行多组分反应的高效且环保的一锅法合成多氢奎啉。提出了可能的转化机制。该过程的特点是温和的反应条件、无需外部催化剂、良好的产率以及在室温下的操作简便性。

  DOI：

  10.1016/j.crci.2010.09.009

文献信息

• Protic pyridinium ionic liquid as a green and highly efficient catalyst for the synthesis of polyhydroquinoline derivatives via Hantzsch condensation in water
  作者：Mahmood Tajbakhsh、Heshmatollah Alinezhad、Mohammad Norouzi、Saeed Baghery、Maryam Akbari

  DOI：10.1016/j.molliq.2012.09.017

  日期：2013.1

  The four-component Hantzsch condensation reaction of dimedone, ethyl acetoacetate, ammonium acetate and various aromatic and aliphatic aldehydes in the presence of 2-methylpyridinium trifluoromethanesulfonate ([2-MPyH]OTf) as a green and highly efficient catalyst in water affords polyhydroquinoline derivatives in good to excellent yields.This reaction has been carried out in the presence of 1 mol% of [2-MPyH]OTf at room temperature. The described novel synthesis method proposes several advantages of short reaction times, high yields, mild condition, high melting point, simplicity and easy workup compared to the traditional method of synthesis. (C) 2012 Elsevier B.V. All rights reserved.
• SUBSTITUTED DIHYDROPYRIDINES FOR SOMATIC EMBRYOGENESIS IN PLANTS
  申请人：STICHTING DIENST LANDBOUWKUNDIG ONDERZOEK

  公开号：US20150296779A1

  公开（公告）日：2015-10-22

  Cyclopentyl 2,7,7-trimethyl-5-oxo-4-(4-pyridinyl)-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylate and similar compounds are potentiators of auxin-induced somatic embryogenesis in plants. In particular, the inventors have discovered certain of these compounds induce somatic embryogenesis in Arabidopsis in the presence of 2,4-D. Also tested is BAY K 8644. Methods of inducing somatic embryogenesis comprise exposing selected plant tissues, e.g. seed embryos, to auxins, e.g. 2.4-D and the compounds.
• One-pot multi-component synthesis of polyhydroquinolines at ambient temperature
  作者：K.A. Undale、T.S. Shaikh、D.S. Gaikwad、D.M. Pore

  DOI：10.1016/j.crci.2010.09.009

  日期：2011.5

  Résumé An efficient and eco-friendly one-pot synthesis of polyhydroquinolines at ambient temperature from the multi-component reaction of aldehyde, 1,3-diketone, β-keto ester and ammonium acetate in ethanol medium is described. The probable mechanism of transformation is suggested. The features of this procedure are mild reaction conditions, no need of external catalyst, good yields and the operational simplicity at ambient temperature.

  摘要 描述了一种在室温下通过醛、1,3-二酮、β-酮酯和乙酸铵在乙醇介质中进行多组分反应的高效且环保的一锅法合成多氢奎啉。提出了可能的转化机制。该过程的特点是温和的反应条件、无需外部催化剂、良好的产率以及在室温下的操作简便性。