9-oxo-9H-fluoren-6-yl trifluoromethanesulfonate | 895130-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-oxo-9H-fluoren-6-yl trifluoromethanesulfonate
• CAS: 895130-48-0
• 化学式: C₁₄H₇F₃O₄S
• 分子量: 328.268
• InChiKey: VXKUXTWNJFNXGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  9-oxo-9H-fluoren-6-yl trifluoromethanesulfonate 在 sodium tetrahydroborate 、 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 三溴化磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.25h， 生成 9-bromo-3-hexyl-9H-fluorene
  参考文献：
  名称：

  Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth

  摘要：

  A series of fluorene-based derivatives was synthesized and evaluated for inhibiting both InhA and Mycobacterium tuberculosis growth. These compounds were inspired by the previously reported Genz-10850 molecule, a good InhA inhibitor, but with a poor activity against M. tuberculosis growth. Structure activity relationships were performed by introducing the following chemical modifications: 1) the piperazine ring; 2) the amide group; 3) the aryl moiety; and 4) the fluorene moiety. Among these new derivatives, one of them was more effective against both the InhA activity and mycobacterial growth, compared to the hit compound. Docking studies were also performed to rationalize activities of these derivatives. Furthermore, we showed for the first time that efflux pump inhibitors potentiated the efficacy of Genz-10850 (GEQ) derivatives against M. tuberculosis growth, demonstrating that these compounds could be substrates of some efflux pumps. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.035
• 作为产物：
  描述：

  2-溴苯甲酸乙酯 在 四(三苯基膦)钯 、 2,6-二叔丁基-4-甲基吡啶 、 甲烷磺酸 、 氢溴酸 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 9.5h， 生成 9-oxo-9H-fluoren-6-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth

  摘要：

  A series of fluorene-based derivatives was synthesized and evaluated for inhibiting both InhA and Mycobacterium tuberculosis growth. These compounds were inspired by the previously reported Genz-10850 molecule, a good InhA inhibitor, but with a poor activity against M. tuberculosis growth. Structure activity relationships were performed by introducing the following chemical modifications: 1) the piperazine ring; 2) the amide group; 3) the aryl moiety; and 4) the fluorene moiety. Among these new derivatives, one of them was more effective against both the InhA activity and mycobacterial growth, compared to the hit compound. Docking studies were also performed to rationalize activities of these derivatives. Furthermore, we showed for the first time that efflux pump inhibitors potentiated the efficacy of Genz-10850 (GEQ) derivatives against M. tuberculosis growth, demonstrating that these compounds could be substrates of some efflux pumps. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.035

文献信息

• Synthesis of <i>meta</i>-arylphenol derivatives <i>via</i> acid-promoted rearrangement of cyclohexadienones
  作者：Hongyan Xie、Minxiang Zhang、Xueyu Fang、Zhaohua Yan、Hua Yao

  DOI：10.1039/d3ob01363d

  日期：——

  A highly effective strategy for the synthesis of meta-arylphenol derivatives through the selective rearrangement of 4-alkyl-4-aryl-2,5-cyclohexadienones under metal-free conditions was developed, in which acid-promoted [1,2]-migration of the aryl group at C-4 occurred exclusively when the alkyl group at C-4 was a methyl group. Treatment of 4-methyl-4-aryl-2,5-cyclohexadienones with 37% HCl in Ac2O

  开发了一种在无金属条件下通过 4-烷基-4-芳基-2,5-环己二烯酮选择性重排合成间芳基苯酚衍生物的高效策略，其中酸促进[1,2] -迁移仅当C-4处的烷基是甲基时，才会发生C-4处的芳基的取代。在室温下，用 37% HCl 的 Ac 2 O溶液处理 4-甲基-4-芳基-2,5-环己二烯酮，得到多取代间芳基苯基乙酸酯，产率 75-94%。还描述了该方案在多环芳香族化合物合成中的应用。
• Preparation and biochemical evaluation of fluorenone-containing lipid analogs
  作者：Thomas A. Spencer、Pingzhen Wang、Janeta V. Popovici-Müller、Ithan D. Peltan、Phoebe E. Fielding、Christopher J. Fielding

  DOI：10.1016/j.bmcl.2006.02.061

  日期：2006.6

  Syntheses are described of fatty acid analogs 5 and 6, and cholesterol (2) analogs 7 and 8 containing fluorenone groups, which are both photoactivable and fluorescent. The potential of the analogs of 2 as biochemical research tools has been demonstrated by the findings that 7 and 8 can replace 2 in apolipoprotein A-I-induced cellular efflux of 2 and that fluorescence is easily visible at the surface of smooth muscle cells equilibrated with 8. (c) 2006 Elsevier Ltd. All rights reserved.