2-(p-tolyl)-7,8-dihydroquinolin-5(6H)-one | 1276536-35-6

• 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: 2-(p-tolyl)-7,8-dihydroquinolin-5(6H)-one
• 英文别名: 2-(p-tolyl)-7,8-dihydro-6H-quinolin-5-one；2-(4-methylphenyl)-7,8-dihydro-6H-quinolin-5-one
• CAS: 1276536-35-6
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: OURFQBLSNQLOGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(p-tolyl)-7,8-dihydroquinolin-5(6H)-one 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 7'-(4-chlorophenyl)-2''-(p-tolyl)-7',7a',7'',8''-tetrahydro-1'H,3'H,5''H-dispiro[indoline-3,5'-pyrrolo[1,2-c]thiazole-6',6''-quinoline]-2,5''-dione
  参考文献：
  名称：

  Synthesis of spiro-linked quinolinone-pyrrolidine/pyrrolo[1,2-c]thiazole-oxindole/acenaphthalene hybrids via multi-component [3 + 2] cycloaddition

  摘要：

  The syntheses of novel spiro-linked quinolinone-pyrrolidine/pyrrolo[1,2-c]thiazole-oxindole/acenaphthalene hybrid heterocycles have been achieved through a one-pot three-component [3 + 2] cycloaddition strategy. The reaction proceeded stereoselectively affording these structurally intriguing multi-spiro compounds in excellent yields. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.10.002
• 作为产物：
  描述：

  (E)-3-(dimethylamino)-1-p-tolylprop-2-en-1-one 、 1,3-环己二酮 在 ammonium acetate 、 L-脯氨酸 作用下， 以 水 为溶剂， 反应 6.0h， 以95%的产率得到2-(p-tolyl)-7,8-dihydroquinolin-5(6H)-one
  参考文献：
  名称：

  Synthesis of spiro-linked quinolinone-pyrrolidine/pyrrolo[1,2-c]thiazole-oxindole/acenaphthalene hybrids via multi-component [3 + 2] cycloaddition

  摘要：

  The syntheses of novel spiro-linked quinolinone-pyrrolidine/pyrrolo[1,2-c]thiazole-oxindole/acenaphthalene hybrid heterocycles have been achieved through a one-pot three-component [3 + 2] cycloaddition strategy. The reaction proceeded stereoselectively affording these structurally intriguing multi-spiro compounds in excellent yields. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.10.002

文献信息

• Pd-catalyzed site selective C–H acetoxylation of aryl/heteroaryl/thiophenyl tethered dihydroquinolinones
  作者：Santhosh Reddy Patpi、Balasubramanian Sridhar、Prabhakar Rao Tadikamalla、Srinivas Kantevari

  DOI：10.1039/c3ra41312h

  日期：——

  Described herein is an efficient protocol for the site selective oxidative C–H activation/acetoxylation of a series of 2-aryl/heteroaryl/thiophenyl tethered dihydroquinolinones using palladium acetate as the catalyst and iodobenzene diacetate as an oxidant. All these transformations progressed well at less sterically encumbered and electronically favourable C–H bonds to give corresponding ortho-acetoxylated derivatives in good yields. Further, acetoxylation of thiophenyl embedded dihydroquinolinones resulted in single regioisomers, acetoxylated at the C-2 position on the thiophenyl moiety. However, when the C-2 position on the thiophene unit was blocked, the acetoxy group was exclusively installed at the C-4 position. Further, we noticed that acetoxylation of dihydroquinolin-5(6H)-one-oxime did not alter ligand preferentiality to give the ortho-acetoxylated product.

  本文描述了一种高效的选择性氧化C–H活化/乙酰氧基化协议，适用于一系列连接有2-芳基/杂芳基/噻吩基的二氢喹啉酮，使用醋酸钯作为催化剂，碘苯二乙酸作为氧化剂。所有这些反应在立体障碍较小且电子性质良好的C–H键上进行良好，生成相应的邻位乙酰氧基化衍生物，收率良好。此外，嵌入噻吩基的二氢喹啉酮的乙酰氧基化反应导致产生单一的区域异构体，乙酰氧基在噻吩基部分的C-2位上。然而，当噻吩单元的C-2位被阻塞时，乙酰氧基则会独占性地安装在C-4位上。此外，我们注意到，二氢喹啉-5(6H)-酮-肟的乙酰氧基化并未改变配体的优先性，仍然生成邻位乙酰氧基化产物。
• Chemoselective Condensation of 3-Amino-2-cyclohexenones with Cinnamaldehydes: Switchable Synthesis of Dihydroquinolinones and Hexahydroacridinediones
  作者：Ling Jiang、Kun He、Weikun Zeng、Zhi Qiao、Xizhong Song、Kaixiu Luo、Jingbo Chen、Jun Lin、Yi Jin

  DOI：10.1021/acs.joc.3c00011

  日期：2023.5.5

  cinnamaldehydes for switchable synthesis of dihydroquinolinones and hexahydroacridinediones was developed. Mechanism analysis showed that the formation of dihydroquinolinones involved trimolecular condensation and oxidative aromatization, while the formation of hexahydroacridinediones involved acid hydrolysis of enaminone and dehydration-aromatization. This strategy provides a convenient way to switch from the

  在此，开发了 3-氨基-2-环己烯酮和肉桂醛的化学选择性缩合，用于二氢喹啉酮和六氢吖啶二酮的可切换合成。机理分析表明，二氢喹啉酮的形成涉及三分子缩合和氧化芳构化，而六氢吖啶二酮的形成涉及烯胺酮的酸水解和脱水-芳构化。该策略提供了一种从相同底物转换为生产两种不同喹啉酮衍生物的便捷方法。
• Synthesis, in vitro, and in vivo (Zebra fish) antitubercular activity of 7,8-dihydroquinolin-5(6H)-ylidenehydrazinecarbothioamides
  作者：Sandeep kumar Marvadi、Vagolu Siva Krishna、Goverdhan Surineni、Rudraraju Srilakshmi Reshma、Balasubramanian Sridhar、Dharmarajan Sriram、Srinivas Kantevari

  DOI：10.1016/j.bioorg.2020.103626

  日期：2020.3

  We, herein, describe the synthesis of a series of novel aryl tethered 7,8-dihydroquinolin-5(6H)-ylidenehydrazinecarbothioamides 4a-v, which showed in vitro and in vivo antimycobacterial activity against Mycobacterium tuberculosis (Mtb) H37Rv. The intermediates dihydro-6H-quinolin-5-ones 3a-v were synthesized from beta-enaminones, reacting with cyclochexane-1,3-dione/5,5-dimethylcyclohexane-1,3-dione and ammonium acetate using a modified Bohlmann-Rahtz reaction conditions. They were further reacted with thiosemicarbazide to give the respective hydrazine carbothioamides 4a-v. All the new analogues 4a-v, were characterized by their NMR and mass spectral data analysis. Among the twenty-two compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC27294), two compounds, 4e and 4j, exhibited the highest inhibition with an MIC of 0.39 mu g/mL. Compounds 4a, 4g, and 4k were found to inhibit Mtb at an MIC of 0.78 mu g/mL. Hydrazinecarbothioamides 4a-k, exhibited enhanced activity than dihydroquinolinones 3a-k. The observed increase in potency provides a clear evidence that hydrazinecarbothioamide is a potential pharmacophore, collectively imparting synergistic effect in enhancing antitubercular activity of the dihydroquinolinone core. The in vivo (Zebra fish) antimycobacterial screening of the in vitro active molecules led to the identification of a hit compound, 4j, with significant activity in the Mtb nutrient starvation model (2.2-fold reduction). Docking studies of 4j showed a hydrogen bond with the P156 residue of the protein.
• Synthesis and antitubercular evaluation of novel substituted aryl and thiophenyl tethered dihydro-6H-quinolin-5-ones
  作者：Srinivas Kantevari、Santhosh Reddy Patpi、Balasubramanian Sridhar、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2010.12.082

  日期：2011.2

  A series of novel aryl and thiophenyl tethered dihydro-6H-quinolin-5-ones have been synthesized in very good yields through CeCl3 center dot 7H(2)O-NaI catalyzed one-pot condensation of beta-enaminones derived from the respective methyl ketones; 1,3-cyclohexanedione & 5,5-dimethyl-1,3-cyclohexanedione and ammonium acetate refluxing in 2-propanol. Dihydro-6H-quinolin-5-ones 3a-f was further derivatized to the respective hydroxymethyl analogs using proline as an organocatalyst in aqueous media. Among the all 18 compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv (MTB), dihydro-6H-quinolin-5-ones 4e and 4f were found to be most active with MIC 3.13 mu g/mL. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of spiro-linked quinolinone-pyrrolidine/pyrrolo[1,2-c]thiazole-oxindole/acenaphthalene hybrids via multi-component [3 + 2] cycloaddition
  作者：Remani Vasudevan Sumesh、Adaikalam Shylaja、Raju Ranjith Kumar、Abdulrahman I. Almansour、Raju Suresh Kumar

  DOI：10.1016/j.tetlet.2018.10.002

  日期：2018.11

  The syntheses of novel spiro-linked quinolinone-pyrrolidine/pyrrolo[1,2-c]thiazole-oxindole/acenaphthalene hybrid heterocycles have been achieved through a one-pot three-component [3 + 2] cycloaddition strategy. The reaction proceeded stereoselectively affording these structurally intriguing multi-spiro compounds in excellent yields. (C) 2018 Elsevier Ltd. All rights reserved.