acide methoxy-9 fluorene-9 carboxylique | 94534-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: acide methoxy-9 fluorene-9 carboxylique
• 英文别名: 9-methoxy-9-fluorenecarboxylic acid；9-methoxy-fluorene-9-carboxylic acid；9-Methoxy-fluoren-9-carbonsaeure；9-Methoxy-<9>-fluorenyl-carbonsaeure；9-Methoxyfluorene-9-carboxylic acid
• CAS: 94534-27-7
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: SLDSXXJFNOYUOU-UHFFFAOYSA-N

物化性质

• 熔点：
  181 °C (decomp)
• 沸点：
  432.1±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  acide methoxy-9 fluorene-9 carboxylique 在 copper(I) oxide 作用下， 以 乙腈 为溶剂， 以100%的产率得到9-methoxyfluorene
  参考文献：
  名称：

  Decarboxylation catalytique et quantitative d'acides arylacetiques en presence'de cuivre I

  摘要：

  DOI：

  10.1016/0040-4020(84)85005-x
• 作为产物：
  描述：

  9-羟基-9-芴甲酸甲酯 在 sodium hydroxide 、 silver(l) oxide 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 生成 acide methoxy-9 fluorene-9 carboxylique
  参考文献：
  名称：

  Detection and Characterization of a Transient Zwitterion, the 9-Carboxylate-9-fluorenyl Cation, and Its Conjugate Acid¹

  摘要：

  Laser flash photolysis of 9-hydroxy-9-fluorenecarboxylic acid in hexafluoro-2-propanol (HFIP) generates a transient with lambda(max) at 495 nm that reacts with nucleophiles such as methanol and bromide and is insensitive to oxygen. In the presence of 0.15 M trifluoroacetic acid, a different transient with lambda(max) at 560 nm that also reacts with nucleophiles is formed. The 495 and 560 nm species are identified as a zwitterion (the 9-carboxylate-9-fluorenyl cation) and its conjugate acid (the 9-carboxy-9-fluorenyl cation), respectively. The assignment of the zwitterion is supported by the observation of infrared absorptions in the carboxylate region that are quenched by nucleophiles with rate constants similar to those obtained by UV-visible detection. Both the zwitterion and its protonated form are observed at intermediate acid concentrations, leading to an estimate of 1 x 10(-2) M(-1) for the equilibrium constant for the ionization of the 9-carboxy-9-fluorenyl cation in HFIP. Absolute rate constants for reaction of the zwitterion with alcohols, anionic nucleophiles, and substituted aromatics are reported and compared to data for other 9-fluorenyl cations.

  DOI：

  10.1021/ja962066t

文献信息

• Bergmann, Chemische Berichte, 1930, vol. 63, p. 1626
  作者：Bergmann

  DOI：——

  日期：——
• Schlenk; Bergmann, Justus Liebigs Annalen der Chemie, 1928, vol. 463, p. 208
  作者：Schlenk、Bergmann

  DOI：——

  日期：——
• Kliegl, Chemische Berichte, 1929, vol. 62, p. 1330
  作者：Kliegl

  DOI：——

  日期：——
• Klinger, Justus Liebigs Annalen der Chemie, 1912, vol. 390, p. 374
  作者：Klinger

  DOI：——

  日期：——
• TOUSSAINT, O.;CAPDEVIELLE, P.;MAUMY, M., TETRAHEDRON, 1984, 40, N 17, 3229-3233
  作者：TOUSSAINT, O.、CAPDEVIELLE, P.、MAUMY, M.

  DOI：——

  日期：——