2-(4-chlorophenyl)-N-methylethene-1-sulfonamide

• 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-chlorophenyl)-N-methylethene-1-sulfonamide
• 英文别名: (E)-2-(4-chlorophenyl)-N-methylethenesulfonamide
• 化学式: C₉H₁₀ClNO₂S
• mdl: MFCD08873130
• 分子量: 231.703
• InChiKey: FXSCJMXVFQCVCY-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-N-methylethene-1-sulfonamide 、 3-溴丙烯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 (E)-N-allyl-2-(4-chlorophenyl)-N-methylethenesulfonamide
  参考文献：
  名称：

  Desulfonylation-Initiated Distal Alkenyl Migration in Copper-Catalyzed Alkenylation of Unactivated Alkenes

  摘要：

  A novel and efficient protocol for desulfonylation-initiated distal alkenyl migration and its application to the elusive alkenylation of unactivated alkenes have been presented. This radical cascade process has successfully achieved the vicinal difluoroalkylalkenylation of unactivated alkenes with excellent chemo-, regio-, and stereoselectivity in high efficiency under mild conditions. The reactions afford previously unknown 3,3-difluoro-S-styrylpiperidin-2-one derivatives or beta-styryl-gamma-difluoroalkyl amines bearing a quaternary stereocenter. This is the first report of difunctionalization of unactivated alkenes through desulfonylation-initiated distal alkenyl migration.

  DOI：

  10.1021/acs.orglett.8b02840
• 作为产物：
  描述：

  4-氯苯乙烯 在 氯化亚砜 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 2-(4-chlorophenyl)-N-methylethene-1-sulfonamide
  参考文献：
  名称：

  Desulfonylation-Initiated Distal Alkenyl Migration in Copper-Catalyzed Alkenylation of Unactivated Alkenes

  摘要：

  A novel and efficient protocol for desulfonylation-initiated distal alkenyl migration and its application to the elusive alkenylation of unactivated alkenes have been presented. This radical cascade process has successfully achieved the vicinal difluoroalkylalkenylation of unactivated alkenes with excellent chemo-, regio-, and stereoselectivity in high efficiency under mild conditions. The reactions afford previously unknown 3,3-difluoro-S-styrylpiperidin-2-one derivatives or beta-styryl-gamma-difluoroalkyl amines bearing a quaternary stereocenter. This is the first report of difunctionalization of unactivated alkenes through desulfonylation-initiated distal alkenyl migration.

  DOI：

  10.1021/acs.orglett.8b02840

文献信息

• Desulfonylation-Initiated Distal Alkenyl Migration in Copper-Catalyzed Alkenylation of Unactivated Alkenes
  作者：Xiaoyang Wang、Jing Liu、Ze Yu、Minjie Guo、Xiangyang Tang、Guangwei Wang

  DOI：10.1021/acs.orglett.8b02840

  日期：2018.10.19

  A novel and efficient protocol for desulfonylation-initiated distal alkenyl migration and its application to the elusive alkenylation of unactivated alkenes have been presented. This radical cascade process has successfully achieved the vicinal difluoroalkylalkenylation of unactivated alkenes with excellent chemo-, regio-, and stereoselectivity in high efficiency under mild conditions. The reactions afford previously unknown 3,3-difluoro-S-styrylpiperidin-2-one derivatives or beta-styryl-gamma-difluoroalkyl amines bearing a quaternary stereocenter. This is the first report of difunctionalization of unactivated alkenes through desulfonylation-initiated distal alkenyl migration.