2-Methyl-3-ethoxycarbonyl-4-phenyl-5-oxo-4,5-dihydro-1H-indeno<1,2-b>pyridine | 26576-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-Methyl-3-ethoxycarbonyl-4-phenyl-5-oxo-4,5-dihydro-1H-indeno<1,2-b>pyridine
• 英文别名: 2-methyl-4-phenyl-5-oxo-4,5-dihydro-1H-indeno-[1,2-b]pyridine-3-carboxylic acid ethyl ester；3-Ethoxycarbonyl-2-methyl-4-phenyl-5-oxo-4,5-dihydro-1H-indeno<1,2-b>pyridine；3-ethoxycarbonyl-2-methyl-4-phenyl-5-oxo-1,4-dihydroindeno<1,2-b>pyridine；ethyl 4-(phenyl)-2-methyl-5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylate；ethyl 2-methyl-5-oxo-4-phenyl-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylate；ethyl 4,5-dihydro-2-methyl-5-oxo-4-phenyl-1H-indeno[1,2-b]pyridine-3-carboxylate；ethyl 2-methyl-5-oxo-4-phenyl-1,4-dihydroindeno[1,2-b]pyridine-3-carboxylate
• CAS: 26576-79-4
• 化学式: C₂₂H₁₉NO₃
• 分子量: 345.398
• InChiKey: CDNOFXHQJUJZNU-UHFFFAOYSA-N

物化性质

• 熔点：
  252-254 °C
• 沸点：
  534.4±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  2-Methyl-3-ethoxycarbonyl-4-phenyl-5-oxo-4,5-dihydro-1H-indeno<1,2-b>pyridine 在 劳森试剂 作用下， 以 苯 为溶剂， 反应 0.33h， 以55%的产率得到2-Methyl-3-ethoxycarbonyl-4-phenyl-5-thioxo-1H-4,5-dihydroindeno<1,2-b>pyridine
  参考文献：
  名称：

  4-芳基-5-thioxo-4,5-二氢茚并[1,2-b]吡啶的合成

  摘要：

  DOI：

  10.1007/bf00519546
• 作为产物：
  描述：

  3-氨基巴豆酸乙酯 、 2-(苯基亚甲基)茚-1,3-二酮 在 溶剂黄146 作用下， 生成 2-Methyl-3-ethoxycarbonyl-4-phenyl-5-oxo-4,5-dihydro-1H-indeno<1,2-b>pyridine
  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。
• One‐pot synthesis of 1,4‐dihydropyridines and <i>N</i> ‐arylquinolines in the presence of copper complex stabilized on MnFe ₂ O ₄ (MFO) as a novel organic–inorganic hybrid material and magnetically retrievable catalyst
  作者：Najmieh Ahadi、Akbar Mobinikhaledi、Mohammad Ali Bodaghifard

  DOI：10.1002/aoc.5822

  日期：2020.10

  The prepared organic–inorganic hybrid material was successfully used as an efficient and recoverable catalyst for the synthesis of 1,4‐dihydropyridines and N‐arylquinolines under mild and green reaction conditions. The results showed that the catalyst exhibited excellent catalytic activity under optimum reaction conditions and the desired products were obtained in good to excellent yields. The new

  在这项工作中，提出了基于席夫碱封装在二氧化硅层中的锰铁氧体纳米粒子的功能化以及随后引入铜的非均相催化剂的设计和合成。通过使用傅立叶变换红外光谱，X射线粉末衍射，场发射扫描电子显微镜，透射电子显微镜，能量色散X射线光谱，差示热重量分析，振动样品磁强分析和感应耦合等离子体来表征合成的混合材料光学发射光谱技术。制备的有机-无机杂化材料已成功用作合成1,4-二氢吡啶和N的有效且可回收的催化剂-芳基喹啉在温和和绿色的反应条件下。结果表明，该催化剂在最佳反应条件下表现出优异的催化活性，并且以良好至优异的产率获得了所需的产物。通过傅立叶变换红外光谱，1 H NMR和碳，氢和氮（CHN）分析的元素分析对新型1,4-二氢吡啶和N-芳基喹啉进行了表征。催化剂可重复使用性的研究证实，该催化剂可循环使用五次，但催化活性略有下降，铜的浸出可忽略不计。
• 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。
• Synthesis and alkylation of 4-aryl-5-oxo-1h-2,3,4,5-tetrahydroindeno[1,2-b]pyridines*
  作者：S. Stupnikova、E. Petushkova、D. Tanajev、V. Lusis、D. Muceniece

  DOI：10.1007/s10593-010-0595-x

  日期：2010.11

  Reduction of 5-oxo-4-phenyl-1H-4,5-dihydroindeno[1,2-b]pyridines with triethylsilane in trifluoro-acetic acid gave the corresponding 1,2,3,4-tetrahydroindeno[1,2-b]pyridines predominatly with the trans-configured substituents at atoms C(2), C(3), and C(4). Alkylation of the anionic form of the tetrahydroindenopyridines gives the N- and C(4a)-alkyl derivatives.

  在三氟乙酸中用三乙基硅烷还原5-氧代-4-苯基-1H-4,5-二氢茚并[1,2- b ]吡啶得到相应的1,2,3,4-四氢茚并[1,2- b ]吡啶主要在原子C（2），C（3）和C（4）处具有反式取代基。四氢茚并吡啶的阴离子形式的烷基化得到N-和C（4a）-烷基衍生物。
• 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.