5-chloro-9-oxo-1-fluorencarboxylic acid | 146516-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5-chloro-9-oxo-1-fluorencarboxylic acid
• 英文别名: 5-chloro-9-oxofluorene-1-carboxylic acid
• CAS: 146516-86-1
• 化学式: C₁₄H₇ClO₃
• 分子量: 258.661
• InChiKey: PXRSHSOQEIOJJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5-chloro-9-oxo-1-fluorenanilide 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 以90%的产率得到5-chloro-9-oxo-1-fluorencarboxylic acid
  参考文献：
  名称：

  Application of organolithium and related reagents in synthesis, Part X. Metallation-electrophilic substitution sequence of secondary chlorobenzamides

  摘要：

  The lithiation (Bu(n)Li/THF) of 2-chloro- (1), 3-chloro- (2) and 4-chlorobenzanilides (3) and the subsequent reactions of the corresponding bis-lithiated anilides 4 - 6 with electrophiles (MeI, CH2 = CH - CH2Br, Me3SiCl, MeCHO, o-MeOC6H4CHO, p-MeOC6H4CHO, Me2NCHO and p-MeOC6H4CONMe2) towards the synthesis of the ortho substituted chlorobenzoesic acids derivatives 12 - 14 have been described. The effect of the chlorine substituent upon the generation and stability of the bis-lithiated chloro-anilides 4 - 6 has been studied. It has been found that the bis-lithiated chloro-anilide 5 derived from m-chloro-benzanilide (2) at a temperature above - 30-degrees-C converts into the corresponding benzyne 9. The anilide moiety (masking group) of the formed ortho-substituted chlorobenzanilides appeared to be effectively removable on acid-driven hydrolysis.

  DOI：

  10.1007/bf00808275