(E)-4,4,5,5-tetramethyl-2-(tridec-1-enyl)-1,3,2-dioxaborolane | 172512-83-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: (E)-4,4,5,5-tetramethyl-2-(tridec-1-enyl)-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-tetramethyl-2-[(E)-tridec-1-enyl]-1,3,2-dioxaborolane
• CAS: 172512-83-3
• 化学式: C₁₉H₃₇BO₂
• 分子量: 308.313
• InChiKey: ZTGHDYUJZMWJOI-WUKNDPDISA-N

物化性质

• 沸点：
  345.5±25.0 °C(Predicted)
• 密度：
  0.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 4-acryloyl-2,2-dimethyloxazolidine-3-carboxylate 、 (E)-4,4,5,5-tetramethyl-2-(tridec-1-enyl)-1,3,2-dioxaborolane 在 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 2,6-二甲基-2,5-环己二烯-1,4-二酮 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以54%的产率得到N-tert-butoxycarbonyl (4S)-4-[1'-oxo-(2'E,4'E)-hexadecadienyl]-2,2-dimethyl-1,3-oxazolidine
  参考文献：
  名称：

  Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes

  摘要：

  We introduce an oxidative Heck reaction for selective complex diene and polyene formation. The reaction proceeds via oxidative Pd(II)/sulfoxide catalysis that retards palladium-hydride isomerizations which previously limited the Heck manifold's capacity for furnishing stereodefined conjugated dienes. Limiting quantities of nonactivated terminal olefins (1 equiv) and slight excesses of vinyl boronic esters (1.5 equiv) that feature diverse functionality can be used to furnish complex dienes and polyenes in good yields and excellent selectivities (generally E:Z = >20:1; internal:terminal = >20:1). Because this reaction only requires prior activation of a single vinylic carbon, improvements in efficiency are observed for synthetic sequences relative to ones featuring reactions that require activation of both coupling partners.

  DOI：

  10.1021/ja402891m