2-(6,6-dimethyl-3-(phenylsulfonyl)octa-1,7-dien-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1509927-11-0

• 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-(6,6-dimethyl-3-(phenylsulfonyl)octa-1,7-dien-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1509927-11-0
• 化学式: C₂₂H₃₃BO₄S
• 分子量: 404.379
• InChiKey: VCLSDJDDFVWENO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(6,6-dimethyl-3-(phenylsulfonyl)octa-1,7-dien-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 Hoveyda-Grubbs catalyst second generation 、 对苯醌 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以90%的产率得到2-(3,3-dimethyl-6-(phenylsulfonyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  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 、 5-iodo-3,3-dimethylpent-1-ene 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-(6,6-dimethyl-3-(phenylsulfonyl)octa-1,7-dien-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  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