10-丁烯基-9(10H)-吖啶酮 | 60536-20-1

• 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
• 中文名称: 10-丁烯基-9(10H)-吖啶酮
• 中文别名: 10-丁烯基吖啶酮；10-丁烯基吖啶-9(10H)-酮
• 英文名称: 10-allylacridin-9(10H)-one
• 英文别名: 10-allylacridine-9(10H)-one；N-allyl acridone；10-prop-2-enylacridin-9-one
• CAS: 60536-20-1
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: HMCBGHYUJZCJED-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  387.4±22.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-丁烯基-9(10H)-吖啶酮 在 dihydrogen hexachloroplatinate 、 三氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Acridinium Salt-Based Fluoride and Acetate Chromofluorescent Probes: Molecular Insights into Anion Selectivity Switching

  摘要：

  A series of acridinium salt-based probes capable of detecting fluoride and acetate anions via a nucleophilic attack at the C9 position of the acridinium moiety is reported. The formation of corresponding acridane displays drastic changes, in both UV-vis absorption and fluorescence emission. The sensing mechanism is a reversible process upon treating either tetrafluoroborate salt or an acid.

  DOI：

  10.1021/ol901935g
• 作为产物：
  描述：

  2,3-二氢-1H-喹啉-4-酮 在 sodium hydride 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 24.0h， 生成 10-丁烯基-9(10H)-吖啶酮
  参考文献：
  名称：

  Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones

  摘要：

  N-Unsubstituted beta-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.

  DOI：

  10.1021/jo3011073

文献信息

• Synthesis of Novel Carbohydrate Acridinone Derivatives with Potential Biological Activities using 1,3‐Dipolar Cycloaddition
  作者：Mirta L. Fascio、Norma Beatriz D'Accorso、Rolando F. Pellón、Maite L. Docampo

  DOI：10.1080/00397910701575178

  日期：2007.12

  Abstract Novel 10‐[3‐(6‐hydroxy‐2,2‐dimethyltetrahydrofuro[2,3‐d][1,3]dioxol‐5‐yl)‐4,5‐dihydro‐5‐isoxazolyl]methyl}‐9(10H)‐acridinone derivatives (13–16) were synthesized by 1,3‐dipolar cycloaddition using the carbohydrate derivative as dipole and different 10‐allyl‐9(10H)‐acridinone derivatives (9–12) as dipolarophiles. The new cycloadducts as well as the dipolarophiles precursors were characterized

  摘要 10-[3-(6-hydroxy-2,2-二甲基四氢呋喃[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-5-isoxazolyl]methyl}- 9(10H)-吖啶酮衍生物 (13-16) 是通过 1,3-偶极环加成反应合成的，使用碳水化合物衍生物作为偶极子，不同的 10-烯丙基-9(10H)-吖啶酮衍生物 (9-12) 作为亲偶极体。新的环加合物以及亲偶极体前体通过光谱进行了表征。
• Long wavelength sensitizers for europium(iii) luminescence based on acridone derivatives
  作者：Anjum Dadabhoy、Stephen Faulkner、Peter G. Sammes

  DOI：10.1039/b104541p

  日期：2002.1.23

  The preparation of several acridone derivatives which have been shown to act as sensitizers for europium(III) luminescence at wavelengths longer than 400 nm is described. The efficiency of sensitization increases as the chromophore is held closer to the ion and the inner sphere hydration number of the ion lowered.

  本文描述了几种吖啶酮衍生物的制备，这些衍生物已被证明能在波长超过400 nm的条件下作为铕(III)发光的敏化剂。随着发色团更接近离子，以及离子的内球水合数降低，敏化效率随之提高。
• Tricyclic heterocyclic derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0471516A1

  公开（公告）日：1992-02-19

  The invention relates to tricyclic heterocyclic derivatives, or pharmaceutically-acceptable salts or in vivo hydrolysable esters thereof, which possess anti-cancer activity. The invention also relates to processes for the manufacture of said tricyclic heterocyclic derivatives, to novel pharmaceutical compositions containing them and to the use of said tricyclic heterocyclic derivatives in the manufacture of a medicament for the production of an anti-cancer effect. The invention provides an optionally substituted tricyclic heterocyclic derivative of the formula I wherein A together with the adjacent vinylene group of the 4-oxo-1,4-dihydropyrid-1-yl ring completes a benzene or pyridine ring;    R¹ and R², which may be the same or different, each is (1-4C)alkyl or (1-4C)alkoxy;    and R³ is hydrogen, (1-4C)alkyl or (1-4C)alkoxy;    or a pharmaceutically-acceptable salt or in vivo hydrolysable ester thereof.

  该发明涉及三环杂环衍生物，或其药用盐或体内可水解酯，具有抗癌活性。该发明还涉及制备所述三环杂环衍生物的方法，含有它们的新型药物组合物以及利用所述三环杂环衍生物制造抗癌药物以产生抗癌效果的用途。该发明提供了公式I的可选择取代的三环杂环衍生物，其中A与4-氧代-1,4-二氢吡啶-1-基环的相邻乙烯基团共同形成苯环或吡啶环；R¹和R²，可以相同也可以不同，分别是(1-4C)烷基或(1-4C)烷氧基；R³是氢，(1-4C)烷基或(1-4C)烷氧基；或其药用盐或体内可水解酯。
• DMSO–allyl bromide: a mild and efficient reagent for atom economic one-pot <i>N</i>-allylation and bromination of 2°-aryl amines, 2-aryl aminoamides, indoles and 7-aza indoles
  作者：Suresh Snoxma Smile、Motakatla Novanna、Sathananthan Kannadasan、Ponnusamy Shanmugam

  DOI：10.1039/d1ra08588c

  日期：——

  A mixture DMSO–allyl bromide has been developed as a reagent for an atom economic one-pot N-allylation and aryl bromination under basic conditions. Utilizing this reagent, N-allylation–bromination of a number of 2°-aryl amines, aryl aminoamides, indoles, and 7-aza indoles has been achieved. The scope of the substrates and limitations, the synthetic utility of the products, and a plausible reaction

  DMSO-烯丙基溴混合物已被开发为碱性条件下原子经济一锅N-烯丙基化和芳基溴化的试剂。利用该试剂，已经实现了许多2°-芳基胺、芳基氨基酰胺、吲哚和7-氮杂吲哚的N-烯丙基化-溴化。已经提出了底物的范围和限制、产物的合成用途以及合理的反应机理。
• Synthesis and Antibacterial Activity of New Acridone Derivatives Containing an Isoxazoline Fragment
  作者：T. N. Kudryavtseva、A. Yu. Lamanov、P. I. Sysoev、L. G. Klimova

  DOI：10.1134/s1070363220010077

  日期：2020.1

  A method was developed for the preparation of N-(4-R-4,5-dihydroisoxazol-5-yl)methylacridones by the reaction of aromatic aldehyde oximes with allyl acridones. For the obtained compounds, a high inhibitory activity in relation to test strains of pathogenic microorganisms was revealed, exceeding furacilin.

  开发了一种通过芳族醛肟与烯丙基a啶反应制备N-（4-R-4,5-二氢异恶唑-5-基）甲基ac啶酮的方法。对于所获得的化合物，显示出相对于病原微生物的测试菌株具有高抑制活性，超过了呋喃西林。