N-(9-芴基)三甲基溴化铵 | 6634-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-(9-芴基)三甲基溴化铵
• 英文名称: N-(9-fluorenyl)trimethylammonium bromide
• 英文别名: (9-fluorenyl)trimethylammonium bromide；fluoren-9-yl-trimethyl-ammonium; bromide；Fluoren-9-yl-trimethyl-ammonium; Bromid；(9-Fluorenyl)trimethylammoniumbromid；N,N,N-Trimethyl-9H-fluoren-9-aminium bromide；9H-fluoren-9-yl(trimethyl)azanium;bromide
• CAS: 6634-60-2
• 化学式: Br*C₁₆H₁₈N
• 分子量: 304.23
• InChiKey: LCHMAZCIVWCCEL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.47
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(9-芴基)三甲基溴化铵 在 氨 、 sodium amide 作用下， 生成 dimethyl-(9-methyl-fluoren-9-yl)-amine
  参考文献：
  名称：

  INFLUENCE OF STRUCTURE OF QUATERNARY AMMONIUM IONS ON ORTHO SUBSTITUTION REARRANGEMENT VERSUS 1,2-SHIFT WITH SODIUM AMIDE IN LIQUID AMMONIA. INFLUENCE OF TEMPERATURE.¹

  摘要：

  DOI：

  10.1021/jo01365a021
• 作为产物：
  描述：

  9-羟基芴 在 乙醇 、 氢溴酸 、 溶剂黄146 作用下， 生成 N-(9-芴基)三甲基溴化铵
  参考文献：
  名称：

  Ingold; Jessop, Journal of the Chemical Society, 1929, p. 2361

  摘要：

  DOI：

文献信息

• Equilibrium acidities and homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in N-substituted trimethylammonium and pyridinium cations
  作者：Xian Man Zhang、Frederick G. Bordwell、Michael Van Der Puy、Herbert E. Fried

  DOI：10.1021/jo00063a026

  日期：1993.5

  Equilibrium acidities (pK(HA)s) of the cations in sixteen N-substituted trimethylammonium salts, one N-phenacylquinuclidinium salt, eight N-substituted pyridinium salts, and N-(ethoxycarbonyl)isoquinolinium bromide, together with the oxidation potentials of their conjugate bases, have been determined in dimethyl sulfoxide (DMSO) solution. The acidifying effects of the alpha-trimethylammonium groups (alpha-Me3N+) and the alpha-pyridinium groups (alpha-PyN+) on the adjacent acidic C-H bonds in these cations were found to average about 10 and 18 pK(HA) units, respectively, in DMSO. The homolytic bond dissociation energies of the acidic C-H bonds in these cations, estimated by the combination of the equilibrium acidities with the oxidation potentials of their corresponding conjugate bases (ylides), show that the alpha-trimethylammonium groups destabilize adjacent radicals by 2-6 kcal/mol, whereas alpha-pyridinium groups stabilize adjacent radicals by 3-6 kcal/mol. The effects of alpha-pyridinium groups on the stabilization energies of the radicals derived from these cations were found to be ca. 4-10 kcal/mol smaller than those of the corresponding phenyl groups, whereas their effects on the equilibrium acidities of the cations were 5.4-13.1 pK(HA) units larger. The pK(HA) value of tetramethylammonium cation (Me4N+) was estimated by extrapolation to be about 42 in DMSO.
• Wittig; Felletschin, Justus Liebigs Annalen der Chemie, 1944, vol. 555, p. 133,137,144
  作者：Wittig、Felletschin

  DOI：——

  日期：——
• Anantakrishnan; Pasupati, Proceedings - Indian Academy of Sciences, Section A, 1941, vol. <A> 13, p. 211,216
  作者：Anantakrishnan、Pasupati

  DOI：——

  日期：——
• INFLUENCE OF STRUCTURE OF QUATERNARY AMMONIUM IONS ON ORTHO SUBSTITUTION REARRANGEMENT VERSUS 1,2-SHIFT WITH SODIUM AMIDE IN LIQUID AMMONIA. INFLUENCE OF TEMPERATURE.¹
  作者：CHARLES R. HAUSER、ROBERT M. MANYIK、WALLACE R. BRASEN、PHILIP L. BAYLESS

  DOI：10.1021/jo01365a021

  日期：1955.8
• Ingold; Jessop, Journal of the Chemical Society, 1929, p. 2361
  作者：Ingold、Jessop

  DOI：——

  日期：——