3-methoxy-9H-fluoren-9-ol | 60992-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3-methoxy-9H-fluoren-9-ol
• 英文别名: 3-methoxy-9-fluorenol；3-methoxy-fluoren-9-ol；3-Methoxy-fluorenol-(9)
• CAS: 60992-12-3
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: RBATXUMWGIUBRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-methoxy-9H-fluoren-9-ol 在 盐酸 作用下， 生成 9-Chloro-3-methoxy-9-trimethylsilyl-fluorene
  参考文献：
  名称：

  Reetz,M.T. et al., Chemische Berichte, 1976, vol. 109, p. 2728 - 2742

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(3-甲氧基苯基)苯甲酸乙酯 在 sodium tetrahydroborate 、 甲烷磺酸 作用下， 以 甲醇 为溶剂， 反应 1.25h， 生成 3-methoxy-9H-fluoren-9-ol
  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

• Polar substituent effects in the sodium borohydride reduction of 2- and 3- substituted fluorenones
  作者：G.G. Smith、R.P Bayer

  DOI：10.1016/s0040-4020(01)93246-6

  日期：1962.1

  The kinetics in the sodium borohydride reduction of fluorenone and twelve 2- and 3- substituted fluorenones were determined at three temperatures in isopropyl alcohol and the entropies and enthalpies of activation calculated. A linear Hammett σ ϱ plot was obtained using meta and para σ constants. The positive ϱ value (ϱ = +2·65) confirmed the nucleophilicity of sodium borohydride. Deviations of the

  在异丙醇中的三个温度下测定芴酮和十二个2和3-取代的芴酮在硼氢化钠还原中的动力学，并计算活化的熵和焓。线性哈米特σρ使用得到情节元和对σ常数。ϱ的正值（ϱ = + 2·65）证实了硼氢化钠的亲核性。电子从哈米特相关性偏离哈米特相关性的原因是通过电子通过未取代的环向基态离位到反应位点而引起的。还原反应在过渡状态阶段在很大程度上破坏了这些相互作用。
• Conformational Spin Switching and Spin‐Selective Hydrogenation of a Magnetically Bistable Carbene
  作者：Iris Trosien、Enrique Mendez‐Vega、Tobias Thomanek、Wolfram Sander

  DOI：10.1002/anie.201906579

  日期：2019.10.14

  the "up" position results in the singlet state and switching into the "down" position in the triplet state. The spin control via a remote functional group makes this carbene unique for the study of spin-specific reactions, which is demonstrated for the hydrogenation reaction. Spin switching by switching the conformation of a remote functional group is a novel phenomenon with potential applications

  分子自旋态的控制为调节化学反应的选择性和开发新型的可磁转换材料开辟了道路。3-甲氧基-9-芴基是一种在低温基质中以最低能量单重态和三重态态生成的卡宾，这些态的比率可以通过选择性照射来改变。几乎简并的自旋态的相互转化是由甲氧基的构象变化引起的：将甲氧基切换到“上”位置会导致单峰态，而在三重态下会切换到“向下”位。通过一个远程官能团进行的自旋控制使得该卡宾对于自旋特异性反应的研究而言是独特的，这在氢化反应中得到了证明。
• Substituted fluoren-9-ols
  作者：C. L. Arcus、M. M. Coombs

  DOI：10.1039/jr9540003977

  日期：——
• NISHIDA, AKIKO;FUJII, SEIJI;HAYASHI, HIROYASU;FUJISAKI, SHIZUO;KAJIGAESHI+, MEM. FAC. ENG. YAMAGUCHI UNIV., 1984, 35, N 1, 51-55
  作者：NISHIDA, AKIKO、FUJII, SEIJI、HAYASHI, HIROYASU、FUJISAKI, SHIZUO、KAJIGAESHI+

  DOI：——

  日期：——
• Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth
  作者：Aurélien Chollet、Giorgia Mori、Christophe Menendez、Frédéric Rodriguez、Isabelle Fabing、Maria Rosalia Pasca、Jan Madacki、Jana Korduláková、Patricia Constant、Annaïk Quémard、Vania Bernardes-Génisson、Christian Lherbet、Michel Baltas

  DOI：10.1016/j.ejmech.2015.06.035

  日期：2015.8

  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.