2,4-diphenyl-4,6,7,8-tetrahydroquinolin-5(1H)-one | 130716-50-6

• 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: 2,4-diphenyl-4,6,7,8-tetrahydroquinolin-5(1H)-one
• 英文别名: 2,4-diphenyl-4,6,7,8-tetrahydro-1H-quinolin-5-one
• CAS: 130716-50-6
• 化学式: C₂₁H₁₉NO
• 分子量: 301.388
• InChiKey: ZUHRYNVZKHWIOW-UHFFFAOYSA-N

物化性质

• 熔点：
  206-209 °C
• 沸点：
  514.1±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-diphenyl-4,6,7,8-tetrahydroquinolin-5(1H)-one 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 生成 oxime of 2,4-diphenyl-5-oxo-5,6,7,8-tetrahydroquinoline
  参考文献：
  名称：

  5-Oxohexahydroquinolines, condensed analogs of 1,4-dihydropyridines. Preparation and properties

  摘要：

  DOI：

  10.1007/bf00497218
• 作为产物：
  描述：

  2-(3-氧代-1,3-二苯基丙基)环己烷-1,3-二酮 在 氨 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以90%的产率得到2,4-diphenyl-4,6,7,8-tetrahydroquinolin-5(1H)-one
  参考文献：
  名称：

  5-Oxohexahydroquinolines, condensed analogs of 1,4-dihydropyridines. Preparation and properties

  摘要：

  DOI：

  10.1007/bf00497218

文献信息

• DPTA-catalyzed one-pot regioselective synthesis of polysubstituted pyridines and 1,4-dihydropyridines
  作者：Jianjun Li、Ping He、Chuanming Yu

  DOI：10.1016/j.tet.2012.03.104

  日期：2012.6

  and amines via a one-pot multi-component reaction. The advantages of this protocol include excellent yields, environmentally benign source of nitrogen, mild reaction conditions, and simple manipulation. Different source of nitrogen like urea, thiourea, inorganic ammonium salts, and organic amines were studied. In addition, a novel way was developed for the conversion of primary aliphatic amines into

  以三氟甲磺酸二苯铵（DPAT）为催化剂，通过一锅多组分反应在无溶剂条件下由醛，酮和胺制备高度取代的吡啶和二氢吡啶。该方案的优点包括极高的收率，对环境有益的氮源，温和的反应条件和简单的操作。研究了氮的不同来源，例如尿素，硫脲，无机铵盐和有机胺。另外，开发了一种新颖的方法，用于将伯脂族胺转化为醇。
• Identification of 4,6-diaryl-1,4-dihydropyridines as a new class of neuroprotective agents
  作者：Giammarco Tenti、Javier Egea、Mercedes Villarroya、Rafael León、José Carlos Fernández、Juan Fernando Padín、Vellaisamy Sridharan、Ma Teresa Ramos、J. Carlos Menéndez

  DOI：10.1039/c3md20345j

  日期：——

  A library of 4,6-diaryl-1,4-dihydropyridines was synthesized using a CAN-catalyzed, Hantzsch-related three component reaction starting from ammonium acetate, β-dicarbonyl compounds and a variety of α,β-unsaturated ketones including chalcones, their vinylogs and heteroanalogues. These compounds lack the structural features needed for vascular activity and were found to prevent calcium overload and behave as neuroprotective agents. One of the compounds, bearing a 2-thienyl substituent at C-4, showed the highest neuroprotective activity and was also a moderate antioxidant, being a good lead compound for further studies in this area.

  合成了一系列4,6-二芳基-1,4-二氢吡啶的化合物，采用了一种由氨基乙酸、β-二酮化合物和多种α,β-不饱和酮（包括查尔克酮、其烯基衍生物和杂环类药物）组成的、由CAN催化的与汉茨赫相关的三组分反应。这些化合物缺乏所需的血管活性结构特征，发现能够防止钙过载并表现出神经保护作用。其中一种在C-4位上带有2-噻吩基取代基的化合物显示出最高的神经保护活性，同时也是一种中等强度的抗氧化剂，是该领域进一步研究的良好先导化合物。
• Design and synthesis of 2,4-disubstituted polyhydroquinolines as prospective antihyperglycemic and lipid modulating agents
  作者：Atul Kumar、Siddharth Sharma、Vishwa Deepak Tripathi、Ram Awatar Maurya、Swayam Prakash Srivastava、Gitika Bhatia、A.K. Tamrakar、Arvind Kumar Srivastava

  DOI：10.1016/j.bmc.2009.11.061

  日期：2010.6.1

  A series of 2,4-disubstituted polyhydroquinoline were synthesized and evaluated for their in vivo antihyperglycemic as well as antidyslipidemic activities. Several synthesized compounds have exhibited promising in vivo antihyperglycemic in SLM, STZ-S, and db/db mice model along with significant lipid and TG modulating activity. All these compounds were evaluated in various in vitro models of diabetes to know the possible mechanism of their antihyperglycemic action. Interestingly, compounds 3a-r (diaryl substitution) have exhibited promising protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity whereas, compounds 5a-d (acid substituted) have shown significant glycogen phosphorylase activity. (C) 2009 Published by Elsevier Ltd.
• New 5-Unsubstituted Dihydropyridines with Improved Ca_V1.3 Selectivity as Potential Neuroprotective Agents against Ischemic Injury
  作者：Giammarco Tenti、Esther Parada、Rafael León、Javier Egea、Sonia Martínez-Revelles、Ana María Briones、Vellaisamy Sridharan、Manuela G. López、María Teresa Ramos、J. Carlos Menéndez

  DOI：10.1021/jm500263v

  日期：2014.5.22

  C-5-unsubstituted-C-6-aryl-1,4-dihydropyridines were prepared by a CAN-catalyzed multicomponent reaction from chalcones, beta-dicarbonyl compounds, and ammonium acetate. These compounds were able to block Ca2+ entry after a depolarizing stimulus and showed an improved Ca(V)1.3/ Ca(V)1.2 selectivity in comparison with nifedipine. Furthermore, they were able to protect neuroblastoma cells against Ca2+ overload and oxidative stress models. Their selectivity ratio makes them highly interesting for the treatment of neurological disorders where Ca2+ dyshomeostasis and high levels of oxidative stress have been demonstrated. Furthermore, their low potency toward the cardiovascular channel subtype makes them safer by reducing their probable side effects, in comparison to classical 1,4-dihydropyridines. Some compounds afforded good protective profile in a postincubation model that simulates the real clinical situation of ictus patients, offering a therapeutic window of opportunity of great interest for patient recovery after a brain ischemic episode. Good activities were also found in acute ischemia/reperfusion models of oxygen and glucose deprivation.
• KAZARINOVA, T. D.;MARKOVA, L. I.;XARCHENKO, V. G., XIMIYA GETEROTSIKL. SOED.,(1990) N, S. 511-514
  作者：KAZARINOVA, T. D.、MARKOVA, L. I.、XARCHENKO, V. G.

  DOI：——

  日期：——