ethyl 4-(2,6-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 339370-09-1

• 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-(2,6-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: Ethyl 4-(2,6-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate；ethyl 4-(2,6-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 339370-09-1
• 化学式: C₂₁H₂₃Cl₂NO₃
• 分子量: 408.325
• InChiKey: UGTNEBGJXSWKBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  乙酰乙酸乙酯 、 2,6-二氯苯甲醛 、 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 0.5h， 以90%的产率得到ethyl 4-(2,6-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Nano-zirconia as an excellent nano support for immobilization of sulfonic acid: a new, efficient and highly recyclable heterogeneous solid acid nanocatalyst for multicomponent reactions

  摘要：

  报告了一种新型的、高效的、可回收的纳米催化剂——纳米氧化锆支撑的磺酸，用于合成多组分反应。

  DOI：

  10.1039/c5nj02430g

文献信息

• Synthesis of sulfonated melamine-functionalized Fe3O4@SiO2@Si–(CH2)3@melamine nanoparticles and its application in the synthesis of 4,4’-(aryl methylene)bis(3-methyl-1H-pyrazol-5-ol)s and hexahydroquinolines
  作者：Maryam Soleimani、Ardeshir Khazaei、Negin Sarmasti、Tahereh Akbarpour

  DOI：10.1007/s13738-021-02420-8

  日期：2022.5

  characterized by energy dispersive X-ray analysis (EDX), field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), thermal gravimetric analysis (TGA), vibrating sample magnetometer (VSM), and infrared (IR). The catalytic activity of the synthesized catalyst was investigated in the synthesis of 4,4'-(aryl methylene)bis(3-methyl-1H-pyrazol-5-ol)s and hexahydroquinolines (HHQs)

  在这项工作中，通过简单的方法制备了磺化三聚氰胺功能化的 Fe 3 O 4 @SiO 2 @Si-(CH 2 ) 3 @三聚氰胺纳米颗粒，并通过能量色散 X 射线分析 (EDX)、场发射扫描电子显微镜对其进行了表征。 (FESEM)、透射电子显微镜 (TEM)、热重分析 (TGA)、振动样品磁力计 (VSM) 和红外 (IR)。研究了合成催化剂在合成4,4'-(芳基亚甲基)双(3-甲基-1 H )中的催化活性-pyrazol-5-ol)s 和六氢喹啉 (HHQs) 在无溶剂条件下通过一锅法反应。反应时间短、变废为宝、收率高和无溶剂条件是本工作最重要的优点。
• Synthesis of polyhydroquinoline derivatives via a four-component Hantzsch condensation catalyzed by tin dioxide nanoparticles
  作者：Seyed Mohammad VAHDAT、Fereshteh CHEKIN、Mehdi HATAMI、Maryam KHAVARPOUR、Saeed BAGHERY、Ziba ROSHAN-KOUHI

  DOI：10.1016/s1872-2067(11)60518-4

  日期：2013.4

  Tin dioxide (SnO2) nanoparticles efficiently catalyzed unsymmetrical four-component Hantzsch condensations of various aldehydes, dimedone, ethyl acetoacetate, and ammonium acetate to form polyhydroquinoline derivatives in excellent yields. This novel method offers several advantages over the traditional method of synthesizing these compounds, including safety, mild conditions, short reaction times

  二氧化锡 (SnO2) 纳米粒子有效地催化各种醛、二甲酮、乙酰乙酸乙酯和乙酸铵的不对称四组分 Hantzsch 缩合反应，以优异的产率形成聚氢喹啉衍生物。与合成这些化合物的传统方法相比，这种新方法具有多种优势，包括安全、条件温和、反应时间短、收率高和易于处理。
• One-Pot Synthesis of Hexahydroquinolines via Hantzsch Four-Component Reaction Catalyzed by a Cheap Amino Alcohol
  作者：Shao-Jun Song、Zi-Xing Shan、Yong Jin

  DOI：10.1080/00397910903370626

  日期：2010.9.20

  An economic, efficient access to hexahydroquinolines was found. In the presence of threo-(1S,2S)-2-amino-1-(4′-nitrophenyl)-1,3-propanediol, a waste product formed in the production of chloromycetin, a one-pot, four-component Hantzsch reaction of dimedone, aldehydes, ethyl acetoacetate, and ammonium acetate at room temperature furnished hexahydroquinoline derivatives in excellent yield. A possible

  发现了一种经济、高效的六氢喹啉获取途径。在苏式-(1S,2S)-2-amino-1-(4'-nitrophenyl)-1,3-propanediol 存在下，氯霉素生产过程中形成的一种废物，一锅四组分 Hantzsch二甲酮、醛、乙酰乙酸乙酯和乙酸铵在室温下反应以优异的收率提供六氢喹啉衍生物。还提出了可能的催化机制。
• A solvent-free synthesis of polyhydroquinolines via Hantzsch multicomponent condensation catalyzed by nanomagnetic-supported sulfonic acid
  作者：Somayeh Otokesh、Nadiya Koukabi、Eskandar Kolvari、Ali Amoozadeh、Masoumeh Malmir、Saeede Azhar

  DOI：10.17159/0379-4350/2015/v68a3

  日期：——

  procedure for the synthesis of polyhydroquinolines was developed, involving a one-pot four-component Hantzsch condensation of aromatic aldehydes, 1,3-cyclohexanediones, alkyl acetoacetate and ammonium acetate in the presence of a catalytic amount of nanomagnetic-supported sulfonic acid under solvent-free conditions. The method offers several advantages including high yields, short reaction times, a simple

  开发了一种简单有效的合成聚氢喹啉的方法，该方法涉及在催化量的纳米磁性负载的磺酸存在下，一锅四组分芳香醛，1,3-环己二酮，乙酰乙酸烷基酯和乙酸铵的Hantzsch缩合反应。无溶剂条件下的酸。该方法具有几个优点，包括高产率，短反应时间，简单的后处理程序和催化剂在多次运行中的可重复使用性。此外，通过使用外部磁体，能够容易地从反应混合物中分离出催化剂。
• 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%。