3-((E)-hept-3-en-1-ynyl)thiophene | 1620636-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-((E)-hept-3-en-1-ynyl)thiophene
• 英文别名: 3-[(E)-hept-3-en-1-ynyl]thiophene
• CAS: 1620636-44-3
• 化学式: C₁₁H₁₂S
• 分子量: 176.282
• InChiKey: GUUDIAYMHJRGQC-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-戊烯基硼酸 、 3-(bromoethynyl)thiophene 在 copper(II) ferrite 、 caesium carbonate 作用下， 反应 8.0h， 以87%的产率得到3-((E)-hept-3-en-1-ynyl)thiophene
  参考文献：
  名称：

  Cu-Catalyzed Fe-Driven C_sp–C_sp and C_sp–C_sp2 Cross-Coupling: An Access to 1,3-Diynes and 1,3-Enynes

  摘要：

  An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.

  DOI：

  10.1021/jo5011069

文献信息

• Cu-Catalyzed Fe-Driven C_sp–C_sp and C_sp–C_sp2 Cross-Coupling: An Access to 1,3-Diynes and 1,3-Enynes
  作者：Sabir Ahammed、Debasish Kundu、Brindaban C. Ranu

  DOI：10.1021/jo5011069

  日期：2014.8.15

  An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.