(Z)-5-(tert-butyldimethylsilyl)-3-methyl-2-penten-4-ynenitrile | 1187525-20-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-5-(tert-butyldimethylsilyl)-3-methyl-2-penten-4-ynenitrile
• CAS: 1187525-20-7
• 化学式: C₁₂H₁₉NSi
• 分子量: 205.375
• InChiKey: PBFJMCNGTIFKPW-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-5-(tert-butyldimethylsilyl)-3-methyl-2-penten-4-ynenitrile 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以85%的产率得到(Z)-3-methyl-2-penten-4-ynenitrile
  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：

  zinc cyanide 、 (Z)-4-(tert-butyldimethylsilyl)-1-iodo-2-methyl-1-buten-3-yne 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到(Z)-5-(tert-butyldimethylsilyl)-3-methyl-2-penten-4-ynenitrile
  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