(Z)-2-(4-(tert-butyldimethylsilyl)-2-methylbut-1-en-3-ynyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1187525-07-0

• 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: (Z)-2-(4-(tert-butyldimethylsilyl)-2-methylbut-1-en-3-ynyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: tert-butyl-dimethyl-[(Z)-3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-ynyl]silane
• CAS: 1187525-07-0
• 化学式: C₁₇H₃₁BO₂Si
• 分子量: 306.328
• InChiKey: GCPFDYRNVWTQME-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  (Z)-2-(4-(tert-butyldimethylsilyl)-2-methylbut-1-en-3-ynyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 水 、 sodium hydroxide 、 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.17h， 以84%的产率得到(Z)-4-(tert-butyldimethylsilyl)-1-iodo-2-methyl-1-buten-3-yne
  参考文献：
  名称：

  Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling

  摘要：

  Contrary to all previous reports, bromoboration of propyne with BBr3 proceeds in >= 98% syn-selectivity to produce (Z)-2-bromo-1-propenyldibromoborane (1). Although 1 is readily prone to stereoisomerization, it can be converted to the pinacolboronate (2) of >= 98% isomeric purity by treatment with pinacol, which may then be subjected to Negishi coupling to give trisubstituted (Z)-alkenylpinacolboronates (3) containing various R groups in 73-90% yields. Iodinolysis of 3 affords alkenyl iodides (4) in 80-90% yields. All alkenes isolated and identified are >= 98% Z

  DOI：

  10.1021/ol901566e
• 作为产物：
  描述：

  (叔丁基二甲基)乙炔 、 (Z)-2-(2-bromoprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 正丁基锂 、 zinc dibromide 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以90%的产率得到(Z)-2-(4-(tert-butyldimethylsilyl)-2-methylbut-1-en-3-ynyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling

  摘要：

  Contrary to all previous reports, bromoboration of propyne with BBr3 proceeds in >= 98% syn-selectivity to produce (Z)-2-bromo-1-propenyldibromoborane (1). Although 1 is readily prone to stereoisomerization, it can be converted to the pinacolboronate (2) of >= 98% isomeric purity by treatment with pinacol, which may then be subjected to Negishi coupling to give trisubstituted (Z)-alkenylpinacolboronates (3) containing various R groups in 73-90% yields. Iodinolysis of 3 affords alkenyl iodides (4) in 80-90% yields. All alkenes isolated and identified are >= 98% Z

  DOI：

  10.1021/ol901566e