2-(2-chlorobenzylidene)-1-tetralone | 66045-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(2-chlorobenzylidene)-1-tetralone
• 英文别名: 2-(2-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one；(2E)-2-[(2-chlorophenyl)methylidene]-3,4-dihydronaphthalen-1-one
• CAS: 66045-83-8
• 化学式: C₁₇H₁₃ClO
• 分子量: 268.743
• InChiKey: KAJPIDMXCPXRTG-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-chlorobenzylidene)-1-tetralone 以38%的产率得到
  参考文献：
  名称：

  MOUSTAFA A. H.; SHAMS N. A.; ZAHRAN R. H.; EWEISS N. F., J. PRAKT. CHEM. , 1978, 320, NO 1, 97-106

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯苯甲醛 、 3,4-二氢-1(2H)-萘酮 在 sodium hydroxide 作用下， 反应 2.0h， 生成 2-(2-chlorobenzylidene)-1-tetralone
  参考文献：
  名称：

  Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azo­methine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles

  摘要：

  标题：摘要 一种高效的铜/GanPhos催化的1,3-偶极环加成反应已报告。这种可行的转化提供了一系列具有一个螺环四元和三个三级立体异构中心的光学活性螺[二氢萘-2,3'-吡咯啉]，产率高，ee值也高。该方案具有高对映选择性和对映选择性，广泛的底物范围和温和的反应条件。

  DOI：

  10.1055/s-0040-1706599

文献信息

• Claisen-Schmidt, aza-Michael, cyclization via cascade strategy toward microwave promoted synthesis of imidazo[2,1-b]quinazolines
  作者：Duraipandi Devi Priya、Selvaraj Mohana Roopan

  DOI：10.1080/00397911.2020.1757112

  日期：2020.6.17

  Imidazole blended quinazolines are having a wide run of potential applications in synthetic field. In this current investigation, we reported a modern synthesis with the help of non-conventional energy. Optimization parameters have been stabilized utilizing RSM (Response Surface Method) as well as Taguchi models. The yield obtained from the proposed protocol is significantly higher compared to other routine strategies. The products were explored by implies of H-1, C-13-NMR and HR-MS investigation. Interestingly, cyclization & aromatization has been influenced by KOH in a greater extent. It is critical that the imidazo[1,2-b]quinazolines show intense fluorescence emission, significant stokes shift, and high quantum yield.
• Tetralone derivatives are MIF tautomerase inhibitors and attenuate macrophage activation and amplify the hypothermic response in endotoxemic mice
  作者：János Garai、Marcell Krekó、László Őrfi、Péter Balázs Jakus、Zoltán Rumbus、Patrik Kéringer、András Garami、Eszter Vámos、Dominika Kovács、Viola Bagóné Vántus、Balázs Radnai、Tamás Lóránd

  DOI：10.1080/14756366.2021.1916010

  日期：2021.1.1

  Macrophage migration inhibitory factor (MIF) is a pro-inflammatory cytokine playing crucial role in immunity. MIF exerts a unique tautomerase enzymatic activity that has relevance concerning its multiple functions and its small molecule inhibitors have been proven to block its pro-inflammatory effects. Here we demonstrate that some of the E-2-arylmethylene-1-tetralones and their heteroanalogues efficiently bind to MIF's active site and inhibit MIF tautomeric (enolase, ketolase activity) functions. A small set of the synthesised derivatives, namely compounds (4), (23), (24), (26) and (32), reduced inflammatory macrophage activation. Two of the selected compounds (24) and (26), however, markedly inhibited ROS and nitrite production, NF-κB activation, TNF-α, IL-6 and CCL-2 cytokine expression. Pre-treatment of mice with compound (24) exaggerated the hypothermic response to high dose of bacterial endotoxin. Our experiments suggest that tetralones and their derivatives inhibit MIF's tautomeric functions and regulate macrophage activation and thermal changes in severe forms of systemic inflammation.
• Synthesis of 2‐Aminopyran Derivatives and 3‐Arylpropionitrile Derivatives Catalyzed by KF/Al₂O₃
  作者：Xiang‐shan Wang、Da‐qing Shi、Ya Du、Yan Zhou、Shu‐jiang Tu

  DOI：10.1081/scc-120030692

  日期：2004.12.31

  A series of 2-cyano-3-aryl-3-(3,4-dihydro-1(2H)-naphthalene-one-2-yl) propionitrile derivatives and 2-aminopyran derivatives were synthesized by the KF-Al2O3-catalyzed reaction of malononitrile with 2-arylmethylidene-3,4-dihydro-1(2H)-naphthalenone, 2,6-biarylmethylidene cyclohexanone, or 2,5-biarylmethylidene cyclopenanone in DMF at room temperature. The structure of the later was confirmed by x-ray analysis.
• Reactions of Aliphatic Diazo Compounds: VI. Reactions of Diazomethane and Ethyl Diazoacetate with (E)-2-Arylmethylene-1,2,3,4-tetrahydronaphthalen-1-ones
  作者：A. P. Molchanov、V. S. Korotkov、R. R. Kostikov

  DOI：10.1023/b:rujo.0000036064.74236.19

  日期：2004.4

  Diazomethane and ethyl diazoacetate add to (E)-2-arylmethylene-1,2,3,4-tetrahydronaphthaten-1-ones in a regio- and stereoselective fashion, yielding the corresponding 4'-aryl-1,2,3,4,4',5'-hexahydro-3'H-naphthalene-2-spiro-3'-pyrazol-1-ones. The products formed by addition of ethyl diazoacetate undergo isomerization into 4,5-dihydro-1H-pyrazole derivatives.
• Synthesis and structure of 2-phenyl-4-aryl-3,4,5,6-tetrahydrobenzo[h]quinazolines
  作者：P�l Perj�si、Andr�s F�ldesi、J�zsef Tam�s

  DOI：10.1007/bf00808676

  日期：1993.2

  The reaction of 2-arylidene-1-tetralones 1 with benzamidine gave 2-phenyl-4-aryl-3,4,5,6-tetrahydrobenzo[h]quinazolines 2. Investigations on the tautomeric equilibria of 2 by IR, H-1- and C-13-NMR showed the compounds to exist predominantly in the tautomeric form 2A both in the solid state and in solution. Acetylation and oxidation of the heterocyclic ring of 2 provided further evidence for the structural assignment of the title compounds.