1,4-二甲氧基-9H-芴-9-酮 | 24061-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 1,4-二甲氧基-9H-芴-9-酮
• 英文名称: 1,4-dimethoxy-9H-fluoren-9-one
• 英文别名: 1,4-dimethoxy-9H-fluorenone；1,4-dimethoxy-9-fluorenone；1,4-dimethoxyfluoren-9-one；1,4-dimethoxy-fluoren-9-one；1,4-Dimethoxy-fluoren-9-on
• CAS: 24061-14-1
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: WAZFWQLGOHYIGJ-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  1,4-二甲氧基-9H-芴-9-酮 在 palladium on activated charcoal 邻四氯苯醌 、 氢气 、 三溴化硼 作用下， 以 乙醚 、 二氯甲烷 、 溶剂黄146 为溶剂， 生成 fluorenequinone
  参考文献：
  名称：

  Horner,L.; Baston,D.W., Justus Liebigs Annalen der Chemie, 1973, p. 910 - 935

  摘要：

  DOI：
• 作为产物：
  描述：

  对苯二甲醚 在 selenium 、 硫酸 作用下， 反应 7.5h， 生成 1,4-二甲氧基-9H-芴-9-酮
  参考文献：
  名称：

  A New and Simple Synthesis of Fluoren-9-ones

  摘要：

  乙基环己烯-1-羧酸酯 (1) 在浓硫酸存在下与多种芳香基底发生反应，生成 cis-1,2,3, 4,4a,9a-六氢芴-9-酮 3a-f，经过脱氢后得到相应的芴-9-酮 4a-f，产率良好。还合成了相对于羰基在邻位的烷氧基取代的芴酮。

  DOI：

  10.1055/s-1993-25908

文献信息

• Mimicking the biological activity of diazobenzo[b]fluorene natural products with electronically tuned diazofluorene analogs
  作者：Wei Zeng、T. Eric Ballard、Alexander G. Tkachenko、Virginia A. Burns、Daniel L. Feldheim、Christian Melander

  DOI：10.1016/j.bmcl.2006.07.024

  日期：2006.10

  Under appropriate electronic modulation, simple diazofluorene analogs recapitulate the DNA cleavage activity of kinamycin D under thiol-based reducing conditions. Achieving DNA cleavage under these reducing conditions is key to anticancer activity, as the most active compound, 1-methoxydiazofluorene, inhibits the proliferation of HeLa cells.

  在适当的电子调制下，简单的重氮芴类似物在基于硫醇的还原条件下概括了凯那霉素D的DNA裂解活性。在这些还原条件下实现DNA裂解是抗癌活性的关键，因为最具活性的化合物1-甲氧基重氮芴可抑制HeLa细胞的增殖。
• Microwave-assisted intramolecular palladium-mediated cyclizations of <i>o</i>-iodobenzophenones for methoxy fluoren-9-ones
  作者：Reda A. Haggam

  DOI：10.1080/00397911.2022.2095210

  日期：2022.7.18

  irradiation is an effective tool in organic reactions that required long reaction times under thermal conditions. Herein substituted 2-iodobenzophenones were transformed into substituted fluoren-9-ones via cesium carbonate and bis(triphenylphosphine) palladium(II) chloride with 56–92% yields within 30–45 min under microwave irradiations. A remarkable decrease in the reaction time with high yield products was

  摘要 微波 (MW) 辐照是在热条件下需要较长反应时间的有机反应中的有效工具。在此，取代的 2-碘二苯甲酮通过碳酸铯和双（三苯基膦）氯化钯 (II) 在微波照射下在 30-45 分钟内以 56-92% 的产率转化为取代的 fluoren-9-ones。观察到高产率产物的反应时间显着减少。分离产物在( 1 H/ 13 CNMR)和相关光谱的基础上得到了强调。
• Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation
  作者：Jung-Chih Wan、Jun-Min Huang、Yu-Huei Jhan、Jen-Chieh Hsieh

  DOI：10.1021/ol401063w

  日期：2013.6.7

  Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.
• Annulation Strategies for Benzo[<i>b</i>]fluorene Synthesis:  Efficient Routes to the Kinafluorenone and WS-5995 Antibiotics
  作者：Ghassan Qabaja、Graham B. Jones

  DOI：10.1021/jo0056186

  日期：2000.10.1

  Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of tri-O-methylkinafluorenone, providing an effective alternative td Friedel-Crafts-based approaches. During the course of this work, an acid-promoted quinolactonization of naphthoquinones was also developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C, and functional analogues was demonstrated, and antitumoral activity of this class was determined.
• A Simple Approach to the Synthesis of Fluoren-9-Ones
  作者：M. M. V. Ramana、Prashant V. Potnis

  DOI：10.1080/00397919508015860

  日期：1995.6

  Cyclohexene-1-Carboxylic acid (I) undergoes reaction with various aromatic substrates (2a-i) in presence of Polyphosphoric acid (PPA) at 100 degrees C to give cis-1,2,3,4,4a,9a-hexahydrofluoren-9-ones (3a-i) in good yield. Dehydrogenation of (3a-i) with selenium powder afforded corresponding fluoren-9-ones (4a-i) in high yield.