N-(2-bromoallyl)-N-(but-3-enyl)-4-methylbenzenesulfonamide | 274680-23-8

• 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: N-(2-bromoallyl)-N-(but-3-enyl)-4-methylbenzenesulfonamide
• 英文别名: N-(2-bromoprop-2-enyl)-N-but-3-enyl-4-methylbenzenesulfonamide
• CAS: 274680-23-8
• 化学式: C₁₄H₁₈BrNO₂S
• 分子量: 344.272
• InChiKey: OUDSGGJNAISQSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-氟苯硼酸 、 N-(2-bromoallyl)-N-(but-3-enyl)-4-methylbenzenesulfonamide 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以34%的产率得到N-(but-3-enyl)-N-[2-(4-fluorophenyl)allyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Suppressed β-Hydride Elimination in Palladium-Catalyzed Cascade Cyclization−Coupling Reactions:  An Efficient Synthesis of 3-Arylmethylpyrrolidines

  摘要：

  A novel type of palladium-catalyzed cascade cyclization-coupling reaction that proceeds with suppressed beta-hydride elimination has been found. One of the N-sulfonyl oxygens is suggested to coordinatively stabilize an alkylpalladium intermediate, thus preventing the intermediate from the usual beta-elimination, This is the first sequential palladium-catalyzed coupling reaction where the Suzuki and Heck reactions can compete. The reaction provides an efficient synthetic route to 4-methylene-3-arylmethylpyrrolidines, which are not readily available by other routes.

  DOI：

  10.1021/ol0056426
• 作为产物：
  描述：

  对甲苯磺酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 N-(2-bromoallyl)-N-(but-3-enyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Suppressed β-Hydride Elimination in Palladium-Catalyzed Cascade Cyclization−Coupling Reactions:  An Efficient Synthesis of 3-Arylmethylpyrrolidines

  摘要：

  A novel type of palladium-catalyzed cascade cyclization-coupling reaction that proceeds with suppressed beta-hydride elimination has been found. One of the N-sulfonyl oxygens is suggested to coordinatively stabilize an alkylpalladium intermediate, thus preventing the intermediate from the usual beta-elimination, This is the first sequential palladium-catalyzed coupling reaction where the Suzuki and Heck reactions can compete. The reaction provides an efficient synthetic route to 4-methylene-3-arylmethylpyrrolidines, which are not readily available by other routes.

  DOI：

  10.1021/ol0056426

文献信息

• Formation of Seven-Membered Rings by Ring-Closing Metathesis of Vinyl Bromides
  作者：Vachiraporn Ajavakom、Richard C. D. Brown、Potchanee Pandokrak、Sofia S. Salim、Gamal A. I. Moustafa、Richard K. Bellingham、Joseph T. Hill-Cousins、Anawat Ajavakom

  DOI：10.1055/a-1845-4195

  日期：2022.9

  A Grubbs II catalyst mediated ring-closing metathesis (RCM) of monobrominated dienes is reported to proceed in moderate to good yields (40–80%) where the linking chain contains five atoms, leading to carbocyclic and heterocyclic seven-membered bromoolefins. Notably, RCM to form five-, six-, or eight-membered bromoolefins was unsuccessful, with the exception of one example where RCM afforded diethyl

  据报道，Grubbs II 催化剂介导的单溴二烯的闭环复分解 (RCM) 以中等至良好的产率 (40-80%) 进行，其中连接链包含五个原子，从而产生碳环和杂环七元溴烯烃。值得注意的是，RCM 无法形成五元、六元或八元溴烯烃，但其中一个例子除外，其中 RCM 提供了 3-溴环己-3-烯-1,1-二羧酸二乙酯。在这种情况下，得到溴甲基取代的环己烯作为副产物。通过参与 Suzuki-Miyaura 反应，证明了所选溴烯烃 RCM 产品的效用。在 RCM 条件下，乙烯基卤化物交换 (Br → Cl) 是一种副反应。