ethyl 4,5-dihydro-2-methyl-5-oxo-4-p-tolyl-1H-indeno[1,2-b]pyridine-3-carboxylate | 370091-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: ethyl 4,5-dihydro-2-methyl-5-oxo-4-p-tolyl-1H-indeno[1,2-b]pyridine-3-carboxylate
• 英文别名: ethyl 4-(4-methylphenyl)-2-methyl-5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylate；2-methyl-5-oxo-4-p-tolyl-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylic acid ethyl ester；2-Methyl-5-oxo-4-p-tolyl-4,5-dihydro-1H-indeno[1,2-b]pyridin-3-carbonsaeure-aethylester；ethyl 2-methyl-4-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylate；ethyl 2-methyl-4-(4-methylphenyl)-5-oxo-1,4-dihydroindeno[1,2-b]pyridine-3-carboxylate
• CAS: 370091-02-4
• 化学式: C₂₃H₂₁NO₃
• 分子量: 359.425
• InChiKey: UUSVEGLSWRDKOD-UHFFFAOYSA-N

物化性质

• 熔点：
  237.5-238.5 °C
• 沸点：
  546.5±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  ethyl 4,5-dihydro-2-methyl-5-oxo-4-p-tolyl-1H-indeno[1,2-b]pyridine-3-carboxylate 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 2-methyl-5-oxo-4-p-tolyl-5H-indeno[1,2-b]pyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  453.杂环化合物的新合成。第十部分4-氮杂氟烯

  摘要：

  DOI：

  10.1039/jr9490002134
• 作为产物：
  描述：

  对甲基苯甲醛 在 溶剂黄146 作用下， 生成 ethyl 4,5-dihydro-2-methyl-5-oxo-4-p-tolyl-1H-indeno[1,2-b]pyridine-3-carboxylate
  参考文献：
  名称：

  453.杂环化合物的新合成。第十部分4-氮杂氟烯

  摘要：

  DOI：

  10.1039/jr9490002134

文献信息

• Magnetic Fe₃O₄@SiO₂ Core–Shell Nanoparticles Functionalized with Sulfamic Acid Polyamidoamine (PAMAM) Dendrimer for the Multicomponent Synthesis of Polyhydroquinolines and Dihydro-1H-Indeno[1,2-b] Pyridines
  作者：Soheila Sargazi Karbasaki、Ghodsieh Bagherzade、Behrooz Maleki、Milad Ghani

  DOI：10.1080/00304948.2021.1957644

  日期：2021.9.3

  (2021). Magnetic Fe3O4@SiO2 Core–Shell Nanoparticles Functionalized with Sulfamic Acid Polyamidoamine (PAMAM) Dendrimer for the Multicomponent Synthesis of Polyhydroquinolines and Dihydro-1H-Indeno[1,2-b] Pyridines. Organic Preparations and Procedures International: Vol. 53, No. 5, pp. 498-508.

  (2021)。用氨基磺酸胺（PAMAM）树枝状聚合物功能化的磁性 Fe3O4@SiO2 核壳纳米颗粒，用于多组分合成多氢喹啉和二氢-1H-茚并 [1,2-b] 吡啶。国际有机制剂和程序：卷。53，第 5 期，第 498-508 页。
• Multicomponent one-pot solvent-free synthesis of functionalized unsymmetrical dihydro-1H-indeno[1,2-b]pyridines
  作者：Subhasis Samai、Ganesh Chandra Nandi、Ram Kumar、M.S. Singh

  DOI：10.1016/j.tetlet.2009.10.022

  日期：2009.12

  A simple and efficient synthesis of 4-aryl-4,5-dihydro-1H-indeno[1,2-b]pyridine derivatives has been achieved via a four-component cyclocondensation of 1,3-indanedione, aromatic aldehydes, β-ketoesters and ammonium acetate in one-pot in the absence of catalyst and solvent at room temperature on grinding. The present approach offers several advantages such as shorter reaction times, higher yields, low

  通过1,3-茚满二酮，芳族醛，β-的四组分环缩合反应，可以实现4-芳基-4,5-二氢-1 H-茚并[1,2- b ]吡啶衍生物的简单有效合成在室温下，在不存在催化剂和溶剂的情况下，一锅法制得酮酯和乙酸铵。本方法具有几个优点，例如较短的反应时间，较高的产率，低成本，简单的后处理和容易的纯化。
• Rapid and Efficient Synthesis of 1,4-Dihydropyridines using a Sulfonic Acid-functionalized Ionic Liquid
  作者：Roghayeh Hossein Nia、Manouchehr Mamaghani、Farhad Shirini、Khalil Tabatabaeian、Marzieh Heidary

  DOI：10.1080/00304948.2014.884372

  日期：2014.3.4

  classical Hantzsch synthesis, involve a threecomponent condensation of an aldehyde with ethyl acetoacetate, and ammonia in acetic acid or in refluxing ethanol.13–18 These methods suffer from drawbacks such as long reaction times, lower yields, use of large volumes of organic solvents and harsh refluxing conditions. Several more efficient methods have recently been developed for the synthesis of fused derivatives

  4-Aryl-l,4-dihydropyridines (1,4-DHPs) 是用于治疗心血管疾病的一类主要药物。1,2 它们是 NADH 辅酶的类似物，也是一类重要的药物。 3 当前文献表明，它们具有多种生物活性，例如抗癌、4 支气管扩张、5 抗糖尿病、6 促神经 7 抗心绞痛 8 和其他药理特性。 9 特别是，茚并吡啶最初是作为抗组胺药开发的，10最重要的特权药用支架之一。它们具有杀真菌、细胞毒性、磷酸二酯酶抑制、冠状动脉扩张和钙调节活性，并且是动物精子发生的有用抑制剂。 11,12 通过经典 Hantzsch 合成制备 1,4-二氢吡啶，涉及醛与乙酰乙酸乙酯和氨在乙酸或回流乙醇中的三组分缩合。13-18 这些方法存在反应时间长、产率低、使用大量有机溶剂和回流条件苛刻等缺点。最近开发了几种更有效的方法来合成二氢吡啶的稠合衍生物，包括使用微波、19,20 离子液体、21-23 金属三氟甲磺酸盐、24
• One‐pot synthesis of dihydro-1H-indeno[1,2-b] pyridines and tetrahydrobenzo[b] pyran derivatives using a new and efficient nanocomposite catalyst based on N‐butylsulfonate‐functionalized MMWCNTs-D-NH2
  作者：Fatemeh Adibian、Ali Reza Pourali、Behrooz Maleki、Mehdi Baghayeri、Amirhassan Amiri

  DOI：10.1016/j.poly.2019.114179

  日期：2020.1

  In this study, magnetic multi-walled carbon nanotubes were functionalized with polyamidoamine (PAMAM) dendrimers and modified with butylsulfonate to afford MMWCNTs-D-(CH2)(4)-So(3)H. The synthesized nanocomposite (MMWCNTs-D-(CH2)(4)-SO3H) was characterized by various techniques such as Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray diffraction (XRD) and thermo-gravimetric analysis (TGA). This nanocomposite catalyst effectively catalyzed four and three component reactions for the synthesis of dihydro-1H-Indeno[1,2-b] pyridines and tetrahydrobenzo[b] pyrans (85-98% yield in 15-20 min and 80-98% yield in 12-30 min, respectively). In addition, the magnetically recoverable catalyst could be easily recycled at least five times without significant loss of catalytic activity. In the first step of synthesis of nanocomposite the Fe3O4 nanoparticles were deposited on oxidized MWCNTs, then a modified PAMAM dendrimer was used to bond to the carbonyl groups. Finally MMWCNTs-D-NH2 functionalized with 1,4-butanesultone. (C) 2019 Elsevier Ltd. All rights reserved.
• An eco-benign and highly efficient access to dihydro-1H-indeno[1,2-b]pyridines in 2,2,2-trifluoroethanol
  作者：Samad Khaksar、Milad Gholami

  DOI：10.1016/j.molliq.2014.03.030

  日期：2014.8

  4-Aryl-4,5-dihydro-1H-indeno[1,2-b]pyridine derivatives are synthesized from both electron-deficient and electron-rich substrates in a fast, high yielding, and operationally simple protocol in 2,2,2-trifluoroethanol (TFE). The solvent (TFE) can be readily separated from reaction products and recovered in excellent purity for direct reuse. (C) 2014 Elsevier B.V. All rights reserved.