N-allyl-4-methyl-N-(3-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-en-1-yl)benzenesulfonamide | 1509927-14-3

• 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-allyl-4-methyl-N-(3-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-en-1-yl)benzenesulfonamide
• 英文别名: N-[3-(benzenesulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-enyl]-4-methyl-N-prop-2-enylbenzenesulfonamide
• CAS: 1509927-14-3
• 化学式: C₂₇H₃₆BNO₆S₂
• 分子量: 545.529
• InChiKey: XHSOPJHZFULMOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-allyl-4-methyl-N-(3-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-en-1-yl)benzenesulfonamide 在 Hoveyda-Grubbs catalyst second generation 、 对苯醌 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以93%的产率得到4-(phenylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-2,3,4,7-tetrahydro-1H-azepine
  参考文献：
  名称：

  Synthesis of Functionalized Cyclic Boronates

  摘要：

  Deprotonation of a simple borylated allylic sulfone and subsequent alkylation with certain unsaturated electrophiles provide substrates that are easily converted into functionalized alkenyl boronates with ring sizes from five- to seven-membered. A Chan-Lam reaction on one such substrate afforded an alkoxyallylic sulfone that was readily converted via a (4 + 3)-cycloaddition to a polycycle possessing the ABC ring substructure of ingenol.

  DOI：

  10.1021/ol4029918
• 作为产物：
  描述：

  正丁基锂 、 4,4,5,5-tetramethyl-2-(3-(phenylsulfonyl)prop-1-en-2-yl)-1,3,2-dioxaborolane 、 二异丙胺 、 N-(2-iodoethyl)-N-[(4-methylphenyl)sulfonyl]-prop-2-enamine 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 N-allyl-4-methyl-N-(3-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-en-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis of Functionalized Cyclic Boronates

  摘要：

  Deprotonation of a simple borylated allylic sulfone and subsequent alkylation with certain unsaturated electrophiles provide substrates that are easily converted into functionalized alkenyl boronates with ring sizes from five- to seven-membered. A Chan-Lam reaction on one such substrate afforded an alkoxyallylic sulfone that was readily converted via a (4 + 3)-cycloaddition to a polycycle possessing the ABC ring substructure of ingenol.

  DOI：

  10.1021/ol4029918