2-(4-fluorobenzyl)-4,4-dimethyl-1-tosylpyrrolidine | 1442433-18-2

• 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: 2-(4-fluorobenzyl)-4,4-dimethyl-1-tosylpyrrolidine
• 英文别名: 2-[(4-Fluorophenyl)methyl]-4,4-dimethyl-1-(4-methylphenyl)sulfonylpyrrolidine；2-[(4-fluorophenyl)methyl]-4,4-dimethyl-1-(4-methylphenyl)sulfonylpyrrolidine
• CAS: 1442433-18-2
• 化学式: C₂₀H₂₄FNO₂S
• 分子量: 361.48
• InChiKey: YNGJSXWXNDAYLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-5-(4-fluorophenyl)-2,2-dimethylpent-4-enoic acid 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 9-mesityl-10-methylacridinium tetrafluoroborate 、 苯硫酚 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 2-(4-fluorobenzyl)-4,4-dimethyl-1-tosylpyrrolidine
  参考文献：
  名称：

  Anti-Markovnikov Hydroamination of Alkenes Catalyzed by an Organic Photoredox System

  摘要：

  Herein we report a metal-free method for the direct anti-Markovnikov hydroamination of unsaturated amines. Irradiation of the amine substrates with visible light in the presence of catalytic quantities of easily synthesized 9-mesityl-10-methylacridinium tetrafluoroborate and thiophenol as a hydrogen-atom donor furnished the nitrogen-containing heterocycles with complete regiocontrol. Two examples of intermolecular anti-Markovnikov alkene hydroamination are also disclosed.

  DOI：

  10.1021/ja4031616

文献信息

• DIRECT ANTI-MARKOVNIKOV ADDITION OF ACIDS TO ALKENES
  申请人：THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：US20160096791A1

  公开（公告）日：2016-04-07

  A method of making an anti-Markovnikov addition product, comprises reacting an acid with an alkene or alkyne in a dual catalyst reaction system to the exclusion of oxygen to produce said anti-Markovnikov addition product; the dual catalyst reaction system comprising a single electron oxidation catalyst in combination with a hydrogen atom donor catalyst. Dual catalyst composition useful for carrying out such methods are also described.

  一种制备反马尔科夫尼科夫加成产物的方法，包括在排除氧气的双催化剂反应体系中，使酸与烯烃或炔烃发生反应，以产生所述反马尔科夫尼科夫加成产物；所述双催化剂反应体系包括单电子氧化催化剂与氢原子给体催化剂的组合。还描述了用于执行此类方法的双催化剂组合物。
• Direct anti-markovnikov addition of acids to alkenes
  申请人：The University of North Carolina at Chapel Hill

  公开号：US10017441B2

  公开（公告）日：2018-07-10

  A method of making an anti-Markovnikov addition product, comprises reacting an acid with an alkene or alkyne in a dual catalyst reaction system to the exclusion of oxygen to produce said anti-Markovnikov addition product; the dual catalyst reaction system comprising a single electron oxidation catalyst in combination with a hydrogen atom donor catalyst. Dual catalyst composition useful for carrying out such methods are also described.

  一种制造反马科夫尼科夫加成产物的方法，包括在双催化剂反应体系中，在排除氧气的情况下，使酸与烯烃或炔烃反应，生成所述反马科夫尼科夫加成产物；双催化剂反应体系包括单电子氧化催化剂与氢原子供体催化剂。此外，还介绍了用于实施此类方法的双催化剂组合物。
• Anti-Markovnikov Hydroamination of Alkenes Catalyzed by an Organic Photoredox System
  作者：Tien M. Nguyen、David A. Nicewicz

  DOI：10.1021/ja4031616

  日期：2013.7.3

  Herein we report a metal-free method for the direct anti-Markovnikov hydroamination of unsaturated amines. Irradiation of the amine substrates with visible light in the presence of catalytic quantities of easily synthesized 9-mesityl-10-methylacridinium tetrafluoroborate and thiophenol as a hydrogen-atom donor furnished the nitrogen-containing heterocycles with complete regiocontrol. Two examples of intermolecular anti-Markovnikov alkene hydroamination are also disclosed.