4-(2-chloro-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester | 298231-14-8

• 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: 4-(2-chloro-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 4-(2-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；ethyl 1,4,7,8-tetrahydro-2,7,7-trimethyl-4-(2-chlorophenyl)-5(6H)-oxoquinoline-3-carboxylate；ethyl 4-(2-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 298231-14-8
• 化学式: C₂₁H₂₄ClNO₃
• 分子量: 373.879
• InChiKey: SWNZLJOGBMQQQS-UHFFFAOYSA-N

物化性质

• 熔点：
  208-210 °C(Solv: ethanol (64-17-5))
• 沸点：
  491.5±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-chloro-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester 在 吡啶 、 pyridinium hydrobromide perbromide 、 sodium hydride 、 肼 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.67h， 生成 2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  [EN] DIHYDROPYRIDINE COMPOUNDS FOR TREATING OR PREVENTING METABOLIC DISORDERS
  [FR] COMPOSES DE DIHYDROPYRIDINE PERMETTANT DE TRAITER OU DE PREVENIR DES TROUBLES METABOLIQUES

  摘要：

  公开号：

  WO2005025507A3
• 作为产物：
  描述：

  2-氯苯甲醛 、 3-氨基巴豆酸乙酯 、 5,5-二甲基-1,3-环己二酮 在 乙酸乙酯 作用下， 以 2-PrOH 、 溶剂黄146 为溶剂， 反应 18.0h， 以to give 4-(2-Chloro-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester (1.33 kg, 89% yield, 99% purity)的产率得到4-(2-chloro-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Dihydropyridine compounds for treating or preventing metabolic disorders

  摘要：

  本发明涉及式（I）的二氢吡啶化合物或其药学上可接受的盐、溶剂化合物、笼合物或前药，其中A2、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22和m如本文所定义，并且包括含有这种化合物的组合物。本发明还涉及预防或治疗代谢性疾病，如糖尿病以及与糖尿病相关的疾病和并发症的方法，包括向需要的受试者给予式（I）的化合物或包含这种化合物的组合物。本发明还涉及包含式（I）的化合物的试剂盒。

  公开号：

  US20050203119A1

文献信息

• TEDETA@BNPs as a basic and metal free nanocatalyst for Knoevenagel condensation and Hantzsch reaction
  作者：Arash Ghorbani-Choghamarani、Zahra Heidarnezhad、Bahman Tahmasbi、Gouhar Azadi

  DOI：10.1007/s13738-018-1417-9

  日期：2018.10

  In this work, Boehmite nanoparticles (BNPs) were synthesized in water using commercially available materials and further N,N,N′,N′-tetraethyldiethylentriamin (TEDETA) was supported on the surface of BNPs, and used as organo-basic catalyst in four-component Hantzsch reaction that provides access to pharmaceutically polyhydroquinoline derivatives and Knoevenagel reaction to afford α,β-unsaturated compounds. All products were obtained in excellent yields (89–98%) and good reaction times under green condition such as water and ethanol solvents. This catalyst was characterized using FT-IR, SEM, EDS, and TGA techniques. This catalyst was reused for several times without the significant loss of their catalytic efficiency. In addition, stability of catalyst after recycling was confirmed by TGA, SEM, EDS and FT-IR techniques.

  在这项工作中，采用商业可得的材料在水中合成了水铝石纳米粒子（BNPs），并进一步在BNPs表面负载了N,N,N′,N′-四乙基二乙烯三胺（TEDETA），用于四组分汉茨施反应中的有机碱催化剂，从而获得制药用的多氢喹啉衍生物，并开展克诺文那尔反应以得到α,β-不饱和化合物。所有产物均在绿色条件下如水和乙醇溶剂中以优异的产率（89-98%）和良好的反应时间获得。该催化剂采用FT-IR、SEM、EDS和TGA技术进行表征。该催化剂在多次重复使用后，其催化效率未显著降低。此外，通过TGA、SEM、EDS和FT-IR技术确认了催化剂再生后仍具有良好的稳定性。
• Nickel(II) immobilized on dithizone–boehmite nanoparticles: as a highly efficient and recyclable nanocatalyst for the synthesis of polyhydroquinolines and sulfoxidation reaction
  作者：Arash Ghorbani-Choghamarani、Parisa Moradi、Bahman Tahmasbi

  DOI：10.1007/s13738-018-1526-5

  日期：2019.3

  of polyhydroquinoline derivatives and selective oxidation of sulfides to sulfoxides. The reactions not require very high temperatures or inert atmosphere. The developed heterogeneous catalyst could be easily separated by centrifugation and recycled for several runs without leaching of Nickel from the surface of the catalyst or significant loss of its catalytic activity.

  在这项工作中，在第一步中，通过将NaOH溶液添加到Al（NO 3）3 .9H 2的溶液中，可以轻松制造勃姆石纳米颗粒。室温下在水中。然后，将镍-二噻唑酮催化剂负载在勃姆石纳米颗粒上（Ni-dithizone @ boehmite）。Ni-dithizone @ boehmite是一种低成本，无毒且可回收的催化剂，可提供环境友好的反应条件。在第二阶段中，在合成多氢喹啉衍生物和将硫化物选择性氧化为亚砜的过程中研究了该催化剂的催化活性。反应不需要很高的温度或惰性气氛。所开发的非均相催化剂可以很容易地通过离心分离并循环使用几次，而不会从催化剂表面浸出镍或显着降低其催化活性。
• 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
  作者：Ali Amoozadeh、Salman Rahmani、Mehrnoosh Bitaraf、Fatemeh Bolghan Abadi、Elham Tabrizian

  DOI：10.1039/c5nj02430g

  日期：——

  Nano-zirconia-supported sulfonic acid as a novel, highly efficient and recyclable heterogeneous nanocatalyst is reported for the synthesis of multicomponent reactions.

  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。

• Molybdenum- and Tungsten-Based Coordination Polymers as Catalysts for an Efficient and Rapid Synthesis of Hexahydro-5-oxoquinoline-3-carboxylates and 1,4-Dihydropyridine-3,5-dicarboxylates
  作者：Biswanath Das、Malampati Srilatha、Boyapati Veeranjaneyulu、Boddu Shashi Kanth

  DOI：10.1002/hlca.201000354

  日期：2011.5

  rapidly (2 min) in the presence of molybdenum‐ and tungsten‐based coordination polymers [M(Bu3Sn)2O4)]n (M=Mo or W) as catalysts (Schemes 1 and 2; Tables 2 and 3). The products were formed at room temperature in excellent yields (90–98%). The catalysts worked under heterogeneous conditions and were recyclable. The earlier reports for the application of these polymers to conduct organic synthesis are

  在基于钼和钨的配位聚合物[M（Bu 3 Sn）2 O 4）] n（M = Mo或W）作为催化剂（方案1和2；表2和3）。产品在室温下以优异的收率（90–98％）形成。催化剂在非均相条件下工作且可回收。这些聚合物用于进行有机合成的早期报道是有限的。本方法探索了这些催化剂的新的有用的应用。
• Identification of dihydropyridines that reduce cellular tau levels
  作者：Christopher G. Evans、Umesh K. Jinwal、Leah N. Makley、Chad A. Dickey、Jason E. Gestwicki

  DOI：10.1039/c0cc02253e

  日期：——

  A series of dihydropyridines were identified that have an effect on the accumulation of tau, an important target in Alzheimer's disease. The dihydropyridine collection was expanded using the Hantzsch multicomponent reaction to develop preliminary structure–activity relationships.

  一系列二氢吡啶化合物被发现能够影响tau蛋白的积聚，tau蛋白是阿尔茨海默病的重要靶点。通过Hantzsch多组分反应扩展了二氢吡啶库，以初步探究结构-活性关系。