fluorene-2-carboxylic acid ethyl ester | 58473-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: fluorene-2-carboxylic acid ethyl ester
• 英文别名: Fluoren-2-carbonsaeure-aethylester；Fluoren-2-carbonsaeureaethylester；2-Aethoxycarbonyl-fluoren；9H-Fluorene-2-carboxylic acid, ethyl ester；ethyl 9H-fluorene-2-carboxylate
• CAS: 58473-60-2
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: SAFAPOUNUGQSNS-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  392.1±21.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  fluorene-2-carboxylic acid ethyl ester 在 lithium aluminium tetrahydride 、 乙醚 、 苯 作用下， 生成 (9H-Fluoren-2-yl)-methanol
  参考文献：
  名称：

  Preparation of DL-beta-(2-Fluorenyl)alanine¹

  摘要：

  DOI：

  10.1021/jo01086a006
• 作为产物：
  描述：

  9H-芴-2-羧基 酸 在 乙醇 、 硫酸 作用下， 反应 8.0h， 生成 fluorene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovering Potent Inhibitors Against the β-Hydroxyacyl-Acyl Carrier Protein Dehydratase (FabZ) of Helicobacter pylori: Structure-Based Design, Synthesis, Bioassay, and Crystal Structure Determination

  摘要：

  The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC(50) values less than 2 muM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC(50) = 0.86 muM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.

  DOI：

  10.1021/jm8015602

文献信息

• The Substituent Effect. XIII. Solvolysis of 1-(7-Substituted 2-Fluorenyl)ethyl Chlorides and Alkaline Hydrolysis of Ethyl 7-Substituted 2-Fluorenecarboxylates
  作者：Yuho Tsuno、Yoshihiko Tairaka、Masami Sawada、Takahiro Fujii、Yasuhide Yukawa

  DOI：10.1246/bcsj.51.601

  日期：1978.2

  Two sets of rate constants for (i) solvolysis of 1-(7-substituted 2-fluorenyl)ethyl chlorides in both 90 and 80% aqueous acetone and (ii) alkaline hydrolysis of ethyl 7-substituted 2-fluorenecarboxylates in 85% aq EtOH have been determined. Both substituent effects could be correlated excellently with the LArSR relationship; the resulting r+ values (0.82 and 0.47, respectively) were comparable with

  (i) 1-(7-取代 2-芴基)乙基氯在 90% 和 80% 丙酮水溶液中的溶剂分解和 (ii) 7-取代 2-芴羧酸乙酯在 85% 乙醇水溶液中的碱水解的两组速率常数已经确定。两种取代基效应都与 LArSR 关系密切相关；在相同条件下，所得 r+ 值（分别为 0.82 和 0.47）与相应联苯基系统中的 r+ 值相当。ρπ+ 值的比较清楚地表明芴基比联苯基系统更有效地传递π电子效应（1:0.75）。这可以归因于后一个 pi 系统中的扭曲因素。发现 Pi 效应传输的衰减是独立于反应的介入 pi 系统的特征：1。
• Clemmensen reduction of 2-acetylfluorene. Pathways for the formation of 2,3-di(2-fluorenyl)butane and its homologues
  作者：Masahiro Minabe、Masaaki Yoshida、Minoru Fujimoto、Kazuo Suzuki

  DOI：10.1021/jo00873a010

  日期：1976.5
• Discovering Potent Inhibitors Against the β-Hydroxyacyl-Acyl Carrier Protein Dehydratase (FabZ) of <i>Helicobacter pylori</i>: Structure-Based Design, Synthesis, Bioassay, and Crystal Structure Determination
  作者：Lingyan He、Liang Zhang、Xiaofeng Liu、Xianghua Li、Mingyue Zheng、Honglin Li、Kunqian Yu、Kaixian Chen、Xu Shen、Hualiang Jiang、Hong Liu

  DOI：10.1021/jm8015602

  日期：2009.4.23

  The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC(50) values less than 2 muM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC(50) = 0.86 muM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.
• Preparation of DL-beta-(2-Fluorenyl)alanine¹
  作者：D. C. MORRISON

  DOI：10.1021/jo01086a006

  日期：1959.4