3-acetyl-5-bromotropolone

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 3-acetyl-5-bromotropolone
• 英文别名: 3-Acetyl-5-bromo-2-hydroxycyclohepta-2,4,6-trien-1-one
• 化学式: C₉H₇BrO₃
• 分子量: 243.057
• InChiKey: GHZVIHZUEYDAEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetyl-5-bromotropolone 在 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 48.0h， 生成 3-[(E)-2-(1,3-benzodioxol-5-yl)vinyl]-5-bromo-1-phenylcyclohepta[c]pyrazol-8(1H)-one
  参考文献：
  名称：

  含1,3-苯并二恶唑体系的溴，芳基偶氮和杂环稠合的类肌酮的合成与表征

  摘要：

  轻松合成了一系列新型的含1,3-苯并二恶唑的溴，芳基偶氮和杂环稠合的类视黄醇化合物。7-溴，5,7-二溴和5-芳基偶氮取代的3-[（（2 E）-3-（1,3-苯并二氧杂-5-基）丙-2-烯酰基]对苯二酚（2，3，和5，6，7）通过直接溴化或3偶氮偶联反应获得的- [（2- ë）-3-（1,3-苯并二氧戊环-5-基）丙-2-烯酰基]托酚酮（1）分别与苯胺衍生物的溴盐和重氮盐一起使用。3-[（2 E）-3-（1,3-苯并二恶唑-5-基）丙-2-烯酰基] -5-溴麦芽酮（4）是从3-乙酰基-5-溴对苯二酚通过与pot醛的一锅羟醛脱水反应获得的。Tropolones 2,3，和4进行用双功能羟胺盐酸盐和盐酸苯肼，得到相应的isoxazolo-和吡唑并-稠合tropones（亲核环合8，9，10，11，12，13分别地）。J.杂环化​​学。（2012）。

  DOI：

  10.1002/jhet.702

文献信息

• Friedländer reaction of 3-acetyltropolones: Synthesis of naphthyridinyl- and allied heterocyclic-substituted tropolones
  作者：Ming-Zhu Piao、Kimiaki Imafuku

  DOI：10.1002/jhet.5570330230

  日期：1996.3

  Five 3-acetyltropolones reacted with 2-amino-3-pyridinecarbaldehyde to afford the corresponding 3-(1,8-naphthyridin-2-yl)tropolones in excellent yields. In a similar manner, 1,6-naphthyridin-2-yl-,1,7-naphthyridin-2-yl-, 6-pyrido[2,3-b]pyrazinyl-, and 1-methyl-6-pyrazolo[5,4-b]pyridyl-substituted tropolones were prepared. Reactivities of amino-substituted heteroarenecarbaldehydes in these reactions

  五个3-乙酰基丙酮酮与2-氨基-3-吡啶甲醛反应，以极好的收率得到相应的3-（1,8-萘啶-2-基）托洛酮。以类似的方式，1,6-萘啶-2-基-，1,7-萘啶-2-基-，6-吡啶基[2,3- b ]吡嗪基-和1-甲基-6-吡唑并[5 ，4- b制备]吡啶基取代的tropolones。还讨论了这些反应中氨基取代的杂亚芳基甲醛的反应性和产物的性质。
• Facile synthesis of 5-bromotropono[${c}$]-fused pyrazoles and isoxazole
  作者：Yang LI、Liangyu XU、Wentao GAO

  DOI：10.3906/kim-1308-27

  日期：——

  A facile synthesis of a series of new 5-bromotropono[c]pyrazole derivatives (3 and 10--15) as well as 5-bromotropono[c]isoxazole (17) is described, involving a condensation reaction of 3-acetyl-5-bromotropolone (1) with hydrazine monohydrate (2), arylhydrazine hydrochlorides (4--9), and hydroxylamine hydrochloride (16), respectively. All the synthesized compounds were obtained in good yields of 56%--77% and their structures were characterized by spectral data and HRMS.

  描述了一系列新型5-溴萘[ c]吡唑衍生物（3和10-15）以及5-溴萘[ c]异噁唑（17）的简单合成，涉及3-乙酰-5-溴萘酮（1）与水合肼（2）、芳基肼盐酸盐（4-9）和盐酸羟胺（16）之间的缩合反应。所有合成的化合物收率均良好，达到56%-77%，其结构通过谱学数据和高分辨质谱进行了表征。
• First Synthesis of 2-Tropolonylquinoline-4-carboxylic Acid Derivatives via Pfitzinger Reaction in Water
  作者：Wentao Gao、Xiaofei Zhang、Yang Li、Kimiaki Imafuku

  DOI：10.3987/com-10-11960

  日期：——

  A facile and clean synthesis of novel 2-tropolonyl substituted quinoline-4-carboxylic acids via Pfitzinger reaction of 3-acetyltropolone or 3-acetyl-5-bromotropolone with different isatins in water was described. It was the first time that the Pfitzinger reaction was applied to the troponoid field. The structures of all the synthesized compounds were characterized by elemental analysis and spectral

  描述了通过 3-乙酰托酚酮或 3-乙酰-5-溴托酚酮与不同靛红在水中的 Pfitzinger 反应，简便而清洁地合成新型 2-托莨菪基取代的 quinoline-4-羧酸。这是第一次将 Pfitzinger 反应应用于类黄酮场。通过元素分析和光谱数据对所有合成化合物的结构进行了表征。
• A Facile Synthesis of New Troponoid-Bearing Flavonoid-Like Compounds
  作者：Wentao Gao、Yang Li、Mingqin Chang

  DOI：10.3987/com-11-12223

  日期：——

  A facile synthesis of a series of new flavonoid-like troponoid compounds, namely 3-(3-arylacryloyl)-5-bromotropolones (2a-i) and 2-aryl-6-bromocyclohepta[b]pyran-4,9-diones (3a-i) is described, involving the Claisen-Schmidt condensation reaction of 3-acetyl-5-bromotropolone (1) with various substituted benzaldehydes followed by the intramolecular oxidation cyclization reaction through the treatment with I-2/DMSO/H2SO4 system.
• NOVEL STAT3 INHIBITORS IDENTIFIED BY STRUCTURE-BASED VIRTUAL SCREENING INCORPORATING SH2 DOMAIN FLEXIBILITY
  申请人：Board of Regents, The University of Texas System

  公开号：US20220168322A1

  公开（公告）日：2022-06-02

  In one aspect, the present disclosure provides methods of inhibiting STAT3 in a cell comprising contacting the cell with a compound of the formula: (I) wherein the variables are as defined herein. In another aspect, the present disclosure provides methods of using of the compounds disclosed herein for the treatment of cancer.