9-Benzyl-fluoren-9-carbonsaeure | 4709-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-Benzyl-fluoren-9-carbonsaeure
• 英文别名: 9-(Phenylmethyl)-9H-fluorene-9-carboxylic acid；9-benzylfluorene-9-carboxylic acid
• CAS: 4709-69-7
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: CHBCWBFWHHSQLZ-UHFFFAOYSA-N

物化性质

• 沸点：
  429.7±15.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-Benzyl-fluoren-9-carbonsaeure 生成 9-苄基芴
  参考文献：
  名称：

  弱碳酸的酸度。第一部分^ h -酸度规模基于取代芴的电离

  摘要：

  已经测量了一系列取代芴的电离。的H -酸度函数规模已经构建为40-95％（摩尔）二甲亚砜在含有氢氧化四甲铵水。该p ķ一个的碳酸值的范围从17·96（2-硝基芴）至23·41（9-叔丁基芴），相对于18·59的9-苯基芴的值。这些值是针对其他酸度测量进行严格评估的。酸度等级与使用苯胺指标建立的等级密切相关。

  DOI：

  10.1039/j29700000173
• 作为产物：
  描述：

  9-benzyl-fluorene-9-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 生成 9-Benzyl-fluoren-9-carbonsaeure
  参考文献：
  名称：

  Wislicenus; Mocker, Chemische Berichte, 1913, vol. 46, p. 2790

  摘要：

  DOI：

文献信息

• ALIPHATIC CHEMISTRY OF FLUORENE: PART V. SPIRO-KETONES
  作者：P. M. G. Bavin

  DOI：10.1139/v60-153

  日期：1960.7.1

  A novel synthesis is described of 1,2;3,4-dibenzophenanthrene, based on the spiro-ketone (IIIb), which was cleaved by strong base to the acid (VIIb).An example is described of acylation of aliphatic carbon.

  描述了一种新型的合成方法，基于螺环酮（IIIb）合成了1,2;3,4-二苯并蒽，该螺环酮经强碱解离为酸（VIIb）。还描述了一种脂肪碳酰化的示例。
• Vaillant, Annales de Chimie (Cachan, France), 1954, vol. <12> 9, p. 5,37
  作者：Vaillant

  DOI：——

  日期：——
• Synthesis and Structure−Activity Relationships of Cetiedil Analogues as Blockers of the Ca²⁺-Activated K⁺ Permeability of Erythrocytes
  作者：Craig J. Roxburgh、C. Robin Ganellin、Salah Athmani、Alessandra Bisi、Wilma Quaglia、David C. H. Benton、Mark A. R. Shiner、Misbah Malik-Hall、Dennis G. Haylett、Donald H. Jenkinson

  DOI：10.1021/jm001113w

  日期：2001.9.1

  Cetiedil, [2-cyclohexyl-2-(3-thienyl)ethanoic acid 2-(hexahydro-1H-azepin-1-yl)ethyl ester], which blocks the intermediate calcium-activated potassium ion permeability (IKCa) in red blood cells, was used as a lead for investigating structure-activity relationships with the aim of determining the pharmacophore and of synthesizing agents of greater potency. A series of compounds having structures related to cetiedil was made and tested on rabbit erythrocytes. Channel blocking activity within the series was found to correlate well with octanol-water partition coefficients but not with the specific chemical structure of the acid moiety. However, whereas log P for the compounds spans a range of values over 4 orders of magnitude, potency only increases by 2 orders. This suggests that hydrophobic interactions with an active site on the channel are probably not the main determinants of activity. It seems more likely that increased lipophilicity enhances access to the channel, probably from within the cell membrane. In keeping with this interpretation, cetiedil methoiodide was found to be inactive, Triphenylethanoic was found to be a more effective acid grouping than 2-cyclohexyl-2-(3-thienyl)ethanoic, and its 2-(hexahydro-1H-azepin-l-yl)ethyl ester (11) was approximately 3 times more potent than cetiedil. The 9-benzylfluoren-9-yl carboxylic acid ester (21) was found to be approximately 9 times more active than cetiedil, and replacing -CO2- in 21 by an ethynyl (-C dropC-) linkage (compound 26, UCL 1608) increased potency by some 15-fold over that of cetiedil.
• Wislicenus; Mocker, Chemische Berichte, 1913, vol. 46, p. 2790
  作者：Wislicenus、Mocker

  DOI：——

  日期：——
• The acidity of weak carbon acids. Part I. H? acidity scale based on the ionisation of substituted fluorenes
  作者：K. Bowden、A. F. Cockerill

  DOI：10.1039/j29700000173

  日期：——

  measured. An H– acidity function scale has been constructed for 40–95 mole % dimethyl sulphoxide in water containing tetramethylammonium hydroxide. The pKa values of the carbon acids range from 17·96 (2-nitrofluorene) to 23·41 (9-t-butylfluorene), relative to the value of 18·59 for 9-phenylfluorene. These values are critically evaluated with regard to other acidity measurements. The acidity scale compares

  已经测量了一系列取代芴的电离。的H -酸度函数规模已经构建为40-95％（摩尔）二甲亚砜在含有氢氧化四甲铵水。该p ķ一个的碳酸值的范围从17·96（2-硝基芴）至23·41（9-叔丁基芴），相对于18·59的9-苯基芴的值。这些值是针对其他酸度测量进行严格评估的。酸度等级与使用苯胺指标建立的等级密切相关。