N-(9-fluorenyl)pyridinium bromide | 7511-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-fluorenyl)pyridinium bromide
• 英文别名: 9-pyridinium-9H-fluorene bromide；1-fluoren-9-yl-pyridinium; bromide；1-Fluoren-9-yl-pyridinium; Bromid；9-Pyridinium-fluorenylbromid；1-(9H-Fluoren-9-YL)pyridin-1-ium bromide；1-(9H-fluoren-9-yl)pyridin-1-ium;bromide
• CAS: 7511-94-6
• 化学式: Br*C₁₈H₁₄N
• 分子量: 324.22
• InChiKey: LQYUECFZUBFLNP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenyl)pyridinium bromide 在 乙醇 、 铂 作用下， 生成 1-(9-fluorenyl)piperidine
  参考文献：
  名称：

  Antitubercular Studies. I. N-Diphenylmethyl-4-alkylpiperidines^1,2

  摘要：

  DOI：

  10.1021/ja01156a053
• 作为产物：
  描述：

  吡啶 、 9-溴芴 反应 18.0h， 以48%的产率得到N-(9-fluorenyl)pyridinium bromide
  参考文献：
  名称：

  阳离子结构对三唑鎓盐在二甲亚砜中酸度的影响。

  摘要：

  制备了一系列因其不同的电子和空间特性而选择的三唑鎓盐，并使用包围指示剂方法在DMSO中于25°C下测定了其p K a值。各系统的结构变化在所述三唑阳离子的酸性的效果已被认为，特别是检查系统改变电子性质，通过使用量化哈米特的效果σ参数。还报道了产生中性卡宾的偶氮盐的第一个p K a值。这些新数据允许选择适当的碱基，以使这种三唑鎓盐去质子化，并具有使p K a相关的潜力。 本文通过相应的羧苯甲酸酯的亲核性确定的值。

  DOI：

  10.1039/c9ob02258a

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.
• The Michael Condensation of Fluorene with Unsaturated Compounds
  作者：Louis A. Pinck、Guido E. Hilbert

  DOI：10.1021/ja01214a043

  日期：1946.10
• Donau, Ralf; Alder, Lutz; Thurner, Joern-Uwe, Zeitschrift fur Chemie, 1985, vol. 25, # 12, p. 438
  作者：Donau, Ralf、Alder, Lutz、Thurner, Joern-Uwe、Lieberenz, Michael、Tomaschewski, Guenther、Stoesser, Reinhard

  DOI：——

  日期：——
• Thurner, J.-U.; Richter, W.; Koeppel, H., Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 2, p. 213 - 228
  作者：Thurner, J.-U.、Richter, W.、Koeppel, H.、Tomaschewski, G.、Hauser, A.、Binst, G. van

  DOI：——

  日期：——
• Thurner, Joern-Uwe; Richter, Wolfgang; Fiedler, Silvia, Zeitschrift fur Chemie, 1983, vol. 23, # 6, p. 218
  作者：Thurner, Joern-Uwe、Richter, Wolfgang、Fiedler, Silvia、Schaefer, Petra、Tomaschewski, Georg

  DOI：——

  日期：——