1-(bis(4-methoxyphenyl)methyl)quinuclidin-1-ium chloride | 1185875-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(bis(4-methoxyphenyl)methyl)quinuclidin-1-ium chloride
• CAS: 1185875-27-7
• 化学式: C₂₂H₂₈NO₂*Cl
• 分子量: 373.923
• InChiKey: MSMMECXSAZHORN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  [4-[(4-methoxyphenyl)methylidene]cyclohexa-2,5-dien-1-ylidene]-methyloxidanium;chloride 、 奎宁环 以 四氢呋喃 为溶剂， 以67%的产率得到1-(bis(4-methoxyphenyl)methyl)quinuclidin-1-ium chloride
  参考文献：
  名称：

  Organocatalytic Activity of Cinchona Alkaloids: Which Nitrogen Is More Nucleophilic?

  摘要：

  The cinchona alkaloids 1a-d react selectively at the quinuclidine ring with benzyl bromide it and at the quinoline ring with benzhydrylium ions (diarylcarbenium ions). The kinetics of these reactions have been determined photometrically or conductimetrically and are compared with analogous reactions of quinuclidine and quinoline derivatives. Quantum chemical calculations [MP2/6-31 + G(2d p)// B3LYP/6-31G(d)] show that the products obtained by attack at the quinuclidine ring (N-sp3) of quinine are thermodynamically more stable when small alkylating agents (primary alkyl) are used, while the products arising from attack at the quinoline ring (N-sp2) are more stable for bulkier electrophiles (Ar2CH). In some cases, rate and equilibrium constants for their reactions with berizhydrylium ions could be determined. These data gave access to the Marcus intrinsic barriers, which are approximately 20 U mol(-1) lower for attack at the N-sp3-center than at the N-sp2-center.

  DOI：

  10.1021/jo901670w