ester methylique de l'acide methoxy-9 fluorene-9 carboxylique | 146464-79-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: ester methylique de l'acide methoxy-9 fluorene-9 carboxylique
• 英文别名: methyl 9-methoxy-9-fluorenecarboxylate；methyl 9-methoxyfluorene-9-carboxylate；9-methoxy-fluorene-9-carboxylic acid methyl ester；9-Methoxy-fluoren-9-carbonsaeure-methylester；9-Methoxy-fluoren-carbonsaeure-(9)-methylester；Methyl 9-methoxy-9H-fluorene-9-carboxylate
• CAS: 146464-79-1
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: BWHLKQRZMIJZTN-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  371.6±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ester methylique de l'acide methoxy-9 fluorene-9 carboxylique 生成 acide methoxy-9 fluorene-9 carboxylique
  参考文献：
  名称：

  Klinger, Justus Liebigs Annalen der Chemie, 1912, vol. 390, p. 374

  摘要：

  DOI：
• 作为产物：
  描述：

  9H-芴-9-羧酸甲酯 在 silver hexafluoroantimonate 、 溴 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 生成 ester methylique de l'acide methoxy-9 fluorene-9 carboxylique
  参考文献：
  名称：

  Johnston, Linda J.; Kwong, Patrick; Shelemay, Avshalom, Journal of the American Chemical Society, 1993, vol. 115, # 5, p. 1664 - 1669

  摘要：

  DOI：

文献信息

• 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：——
• Formation and Rearrangement of a 2,2-Dimethoxyoxirane from Dimethoxycarbene and Fluorenone
  作者：David L. Pole、John Warkentin

  DOI：10.1021/jo970198e

  日期：1997.6.13

  Thermolysis of 2,2-dimethoxy-5,5-dimethyl-Delta(3)-1,3,4-oxadiazoline (1) at 110 degrees C in the presence of 9-fluorenone (3) yielded 9-(dimethoxymethylene)fluorene oxide (4) and methyl 9-methoxyfluorene-9-carboxylate (5), which are the result of the addition of dimethoxycarbene (2) to the carbonyl group of 9-fluorenone. While the epoxide 4 is most likely generated from direct [2 + 1] cycloaddition, the ester 5 is the result of subsequent rearrangement of the oxirane. Thermolysis of the trideuterio-methoxy oxadiazoline 1-d(3) in the presence of fluorenone showed that 5 is not formed by an intermolecular process because evidence for crossover of the label in the product 5 was not found. The rearrangement of 4 to 5 does not proceed by ring opening and intramolecular methyl transfer either but, instead, by ring opening and intramolecular methoxy transfer. Thus, as predicted by the Baldwin rules, the strained intramolecular 5-endo-tet methyl transfer is avoided in favor of another process.
• Detection and Characterization of a Transient Zwitterion, the 9-Carboxylate-9-fluorenyl Cation, and Its Conjugate Acid¹
  作者：C. S. Q. Lew、B. D. Wagner、Mark P. Angelini、E. Lee-Ruff、J. Lusztyk、L. J. Johnston

  DOI：10.1021/ja962066t

  日期：1996.1.1

  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.