1,2,2-trimethyl-4,4-diphenylpyrrolidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,2-trimethyl-4,4-diphenylpyrrolidine
• 英文别名: 4,4-Diphenyl-1,2,2-trimethylpyrrolidine
• 化学式: C₁₉H₂₃N
• 分子量: 265.398
• InChiKey: KTNGRYCRNAFQBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4,4-Diphenyl-1,2,2-trimethylpyrrolidine N-oxide 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 1,2,2-trimethyl-4,4-diphenylpyrrolidine
  参考文献：
  名称：

  Reverse Cope elimination reactions. 1. Mechanism and scope

  摘要：

  N-4-Pentenyl- and N-5-hexenyl-N-methylhydroxylamine cyclized under mild conditions in a reverse Cope elimination reaction to give 1,2-dimethylpyrrolidine N-oxide and 1,2-dimethylpiperidine N-oxide, respectively. The reaction was shown to be concerted and thermodynamically controlled. The scope of this novel cyclization is discussed, and comparisons are made with the closely related and previously reported cyclization of monosubstituted alkenylhydroxylamines to give cyclic hydroxylamines.

  DOI：

  10.1021/jo00123a013

文献信息

• Mild, Rhodium-Catalyzed Intramolecular Hydroamination of Unactivated Terminal and Internal Alkenes with Primary and Secondary Amines
  作者：Zhijian Liu、John F. Hartwig

  DOI：10.1021/ja710126x

  日期：2008.2.6

  We report a series of mild, rhodium-catalyzed hydroaminations of unactivated olefins with primary and secondary alkylamines to form the corresponding five- and six-membered products in excellent yields. The reactions form exclusively the product from hydroamination without competitive oxidative amination or olefin isomerization with catalysts generated from a biaryl dialkyl phosphine and an analogue

  我们报道了一系列温和的铑催化未活化烯烃与伯烷基胺和仲烷基胺的氢胺化反应，以优异的收率形成相应的五元和六元产物。该反应仅通过加氢胺化形成产物，而无需使用由联芳基二烷基膦和Xantphos类似物产生的催化剂进行竞争性氧化胺化或烯烃异构化。加氢胺化过程可耐受多种官能团，包括羟基、卤素、氰基和烷氧羰基。
• Hydroamination of Alkenes
  申请人：Takemiya Akihiro

  公开号：US20090156824A1

  公开（公告）日：2009-06-18

  A method includes reacting an amino group, a composition including rhodium and an organic ligand, and a substrate having structural formula (I) in a reaction mixture. R 1 is an organic group including a sp 3 carbon atom bonded to C A . R 2 is selected from the group consisting of hydrogen, methyl, and an organic group including a sp 3 carbon atom bonded to C A . R 3 and R 4 independently are selected from the group consisting of hydrogen, methyl, and an organic group including a sp 3 carbon atom bonded to C B . The method further includes forming a hydroaminated product in the reaction mixture.

  一种方法包括在反应混合物中反应氨基基团、包括铑和有机配体的组合物以及具有结构式（I）的底物。其中，R1是包括与CA键合的sp3碳原子的有机基团。R2从氢、甲基和包括与CA键合的sp3碳原子的有机基团的组中选择。R3和R4独立地从氢、甲基和包括与CB键合的sp3碳原子的有机基团的组中选择。该方法进一步包括在反应混合物中形成一个羟胺化产物。
• Cu(I)-Catalyzed Intramolecular Hydroamination of Unactivated Alkenes Bearing a Primary or Secondary Amino Group in Alcoholic Solvents
  作者：Hirohisa Ohmiya、Toshimitsu Moriya、Masaya Sawamura

  DOI：10.1021/ol9007712

  日期：2009.5.21

  bearing an unprotected aminoalkyl substituent in alcoholic solvents, giving pyrrolidine and piperidine derivatives in excellent yields. This system is applicable to both primary and secondary amines and tolerates a variety of functional groups.

  Cu-Xantphos系统[Cu（O- t- Bu）-Xantphos，10-15 mol％]催化未活化末端烯烃的分子内加氢胺化反应，该末端烯烃在醇溶剂中带有未保护的氨基烷基取代基，从而以优异的收率得到吡咯烷和哌啶衍生物。该系统适用于伯胺和仲胺，并且可以耐受多种官能团。
• US8188302B2
  申请人：——

  公开号：US8188302B2

  公开（公告）日：2012-05-29
• Reverse Cope elimination reactions. 1. Mechanism and scope
  作者：Engelbert Ciganek、John M. Read、Joseph C. Calabrese

  DOI：10.1021/jo00123a013

  日期：1995.9

  N-4-Pentenyl- and N-5-hexenyl-N-methylhydroxylamine cyclized under mild conditions in a reverse Cope elimination reaction to give 1,2-dimethylpyrrolidine N-oxide and 1,2-dimethylpiperidine N-oxide, respectively. The reaction was shown to be concerted and thermodynamically controlled. The scope of this novel cyclization is discussed, and comparisons are made with the closely related and previously reported cyclization of monosubstituted alkenylhydroxylamines to give cyclic hydroxylamines.