ethyl 4-(2-chlorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 33323-04-5

• 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-chlorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: ethyl 4-(2-chlorophenyl)-2-methyl-5-oxo-4,6,7,8-tetrahydro-1H-quinoline-3-carboxylate
• CAS: 33323-04-5
• 化学式: C₁₉H₂₀ClNO₃
• 分子量: 345.826
• InChiKey: KHAVUVLSKFFNKD-UHFFFAOYSA-N

物化性质

• 沸点：
  486.8±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  乙酰乙酸乙酯 、 2-氯苯甲醛 、 1,3-环己二酮 在 tetraethylammonium 2-(carbamoyl)benzoate 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以88%的产率得到ethyl 4-(2-chlorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  2-（氨基甲酰基）苯甲酸四乙铵作为双功能有机催化剂，用于一锅法合成Hantzsch 1,4-二氢吡啶和聚氢喹啉衍生物

  摘要：

  摘要已经开发了一种绿色，方便且环境友好的方法，该方法通过在2-乙基氨基甲酸酯苯甲酸四乙铵（一种有效的不含金属的双金属催化剂）存在下合成具有生物活性的Hantzsch 1,4-二氢吡啶和聚氢喹啉衍生物。在回流条件下，各种醛，乙酰乙酸乙酯或环状1,3-二羰基化合物和乙酸铵在EtOH中的一锅多组分反应。所提出的方法能够以直接的后处理和低成本的方法以良好至优异的产率和短的反应时间提供所需的产物。 图形概要

  DOI：

  10.1007/s00706-016-1666-1

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。
• Microwave-Assisted IBX-Mediated One-Pot Four-Component Synthesis of 4-Arylhexahydroquinoline Derivatives from Benzyl Alcohols: A Metal-Free Approach
  作者：D. Khan、Shaily、N. Maurya

  DOI：10.1134/s107042802304019x

  日期：2023.4

  Abstract An operationally convenient microwave-enhanced IBX-mediated one-pot multicomponent reaction has been proposed for the preparation of hexahydrohydoquinoline derivatives from benzyl alcohols, cyclic 1,3-diketones, ammonium acetate, and ethyl acetoacetate. The reaction is likely to involve the oxidation of benzyl alcohol into benzaldehyde and sequential reactions with other components. o-Iodoxybenzoic

  摘要 提出了一种操作方便的微波增强 IBX 介导的一锅多组分反应，用于从苯甲醇、环状 1,3-二酮、乙酸铵和乙酰乙酸乙酯制备六氢喹啉衍生物。该反应可能涉及苯甲醇氧化成苯甲醛以及与其他组分的连续反应。邻碘苯甲酸是一种容易获得的高价碘（V）试剂，被发现在生态友好的环境下对于这种转化非常有效。10 分钟内即可生产出各种取代的六氢喹啉衍生物，收率高达 96%。
• Wu, Chunlei; Shen, Runpu; Tao, Feifei, Journal of the Indian Chemical Society, 2013, vol. 90, # 8, p. 1243 - 1246
  作者：Wu, Chunlei、Shen, Runpu、Tao, Feifei、Gao, Xiaozhong、Deng, Liping、Zhou, Yubo

  DOI：——

  日期：——
• Synthesis of MCM-41 supported cobalt (II) complex for the formation of polyhydroquinoline derivatives
  作者：Saurabh Sharma、Udai P. Singh、A.P. Singh

  DOI：10.1016/j.poly.2021.115102

  日期：2021.5
• 10.1002/aoc.7543
  作者：Rao, Adapaka Venkateswara、Maddila, Suresh、Anantha, Sai Sonali、Robert, Alice Rinky、Jonnalagadda, Sreekantha B.

  DOI：10.1002/aoc.7543

  日期：——

  This work aims to explore the catalytic potential of manganese oxide (MnO2) supported on (Fe3O4‐MWCNT) nano‐composite, which is composed of iron oxide and multi‐walled carbon nanotubes. The nano‐composite was synthesized using a simple impregnation technique. The catalyst material was extensively characterized using a variety of possible analytical methods, including X‐ray diffraction (XRD), Brunauer–Emmett–Teller (BET), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and energy dispersive X‐ray spectroscopy (EDS). Then, utilizing a multi‐component condensation protocol comprising substituted aldehydes, cyclohexadione, ethylacetoacetate, and NH4OAc, the catalytic efficacy of the Fe3O4‐MWCNT@MnO2 nano‐composite was assessed for synthesizing novel hexahydro‐quinoline analogues. The catalyst was found to be effective because of its huge specific surface area, stability, porosity, and distinctive exposed surfaces. The catalyst's surface exhibited an exceptionally active nature, as seen by the notably high turnover frequency. Herein, we present a reusable and effective catalytic method that produces outstanding product yields (93%–97%) under mild reaction conditions, using ethanol as a green solvent. Cost‐effectiveness, environmental safety, and high atom efficiency are achieved using the nano‐composite.