(1R,2S,4S)-N-[4-(trifluoromethyl)phenyl]bicyclo[2.2.1]heptan-2-amine

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,4S)-N-[4-(trifluoromethyl)phenyl]bicyclo[2.2.1]heptan-2-amine
• 化学式: C₁₄H₁₆F₃N
• 分子量: 255.283
• InChiKey: REOBFGLLFXGWGW-CWSCBRNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  对三氟甲基苯胺 、 norbornene 在 mesitylbis(pentafluorphenyl)phosphonium tetrakis(perfluorophenyl)borate 作用下， 以 邻二氯苯 为溶剂， 反应 48.0h， 生成 (1R,2S,4S)-N-[4-(trifluoromethyl)phenyl]bicyclo[2.2.1]heptan-2-amine
  参考文献：
  名称：

  Sterically congested phosphonium borate acids as effective Brønsted acid catalysts

  摘要：

  Phosphonium borate acids [HPPh2(C6F5)][B(C6F5)(4)] (2), [HPMes(2)(C6F5)][B(C6P5)(4)] (3) and [HPMes(C6F5)(2)] [B(C6F5)4] (4) were synthesized via heterolytic dihydrogen cleavage in the presence of triisopropylsilylium and characterized by spectroscopic and crystallographic methods. Bronsted acid catalysis using compounds 2-4 proved to be efficient for a number of challenging reactions (namely ionic hydrogenation, hydroamination and hydroarylation), owing to the restrained nucleophilicity of the sterically hindered conjugate bases. Reactivity of compounds 2-4 suggests that their pK(a) values are similar to that of diethyl oxonium acid. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.05.049

文献信息

• Sterically congested phosphonium borate acids as effective Brønsted acid catalysts
  作者：Arup Sinha、Amit K. Jaiswal、Rowan D. Young

  DOI：10.1016/j.poly.2016.05.049

  日期：2016.12

  Phosphonium borate acids [HPPh2(C6F5)][B(C6F5)(4)] (2), [HPMes(2)(C6F5)][B(C6P5)(4)] (3) and [HPMes(C6F5)(2)] [B(C6F5)4] (4) were synthesized via heterolytic dihydrogen cleavage in the presence of triisopropylsilylium and characterized by spectroscopic and crystallographic methods. Bronsted acid catalysis using compounds 2-4 proved to be efficient for a number of challenging reactions (namely ionic hydrogenation, hydroamination and hydroarylation), owing to the restrained nucleophilicity of the sterically hindered conjugate bases. Reactivity of compounds 2-4 suggests that their pK(a) values are similar to that of diethyl oxonium acid. (C) 2016 Elsevier Ltd. All rights reserved.