2-(4-fluorophenyl)-5-methyl-1-tosylpyrrolidine

• 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-fluorophenyl)-5-methyl-1-tosylpyrrolidine
• 英文别名: 2-(4-Fluorophenyl)-5-methyl-1-(4-methylphenyl)sulfonylpyrrolidine
• 化学式: C₁₈H₂₀FNO₂S
• 分子量: 333.427
• InChiKey: JXFZDHBATZYBLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  4-氟代苯基甲苯 、 对甲苯磺酰胺 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以52%的产率得到2-(4-fluorophenyl)-5-methyl-1-tosylpyrrolidine
  参考文献：
  名称：

  Halogen-Bond-Induced Consecutive C_sp³–H Aminations via Hydrogen Atom Transfer Relay Strategy

  摘要：

  The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular C-sp(3)-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.

  DOI：

  10.1021/acs.orglett.0c00081

文献信息

• SULFONYL-PYRROLIDINE DERIVATIVES USEFUL FOR THE TREATMENT OF NEUROLOGICAL DISORDERS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1299383B1

  公开（公告）日：2005-01-12
• Halogen-Bond-Induced Consecutive C_sp³–H Aminations via Hydrogen Atom Transfer Relay Strategy
  作者：Fan Wu、Jeewani P. Ariyarathna、Navdeep Kaur、Nur-E Alom、Maureen L. Kennell、Omar H. Bassiouni、Wei Li

  DOI：10.1021/acs.orglett.0c00081

  日期：2020.3.20

  The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular C-sp(3)-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.