2-phenylsulfonyl-3-hexylthiophene | 1519969-71-1

• 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-phenylsulfonyl-3-hexylthiophene
• 英文别名: 2-(Phenylsulfonyl)-3-hexylthiophene；2-(benzenesulfonyl)-3-hexylthiophene
• CAS: 1519969-71-1
• 化学式: C₁₆H₂₀O₂S₂
• 分子量: 308.466
• InChiKey: ZGGXZOXHDXPXOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenylsulfonyl-3-hexylthiophene 在 lithium chloro-isopropyl-magnesium chloride 、 二乙胺 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 3-hexyl-5-iodo-2-phenylsulfonylthiophene
  参考文献：
  名称：

  Nickel(II)-Catalyzed Cross-Coupling Polycondensation of Thiophenes via C–S Bond Cleavage

  摘要：

  Cross-coupling polycondensation of thiophene derivatives occurs via C-S bond cleavage in the presence of a nickel catalyst. Head to tail type (HT) regioregular poly(3-hexylthiophene) is obtained by a nickel(II)-catalyzed deprotonative C-H functionalization polycondensation of 2-(phenylsulfonyl)-3-hexylthiophene with stoichiometric TMPMgCl center dot LiCl or with the catalytic secondary amine/RMgX. Debrominative Grignard metathesis (GRIM) polymerization with 5-bromo-2-(phenylsulfonyl)-3-hexylthiophene also proceeds by the catalysis of the nickel(II) complex to afford the corresponding polythiophene.

  DOI：

  10.1021/om4010737
• 作为产物：
  描述：

  2-溴-3-己基噻吩 在 lithium chloro-isopropyl-magnesium chloride 、 双氧水 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.5h， 生成 2-phenylsulfonyl-3-hexylthiophene
  参考文献：
  名称：

  Nickel(II)-Catalyzed Cross-Coupling Polycondensation of Thiophenes via C–S Bond Cleavage

  摘要：

  Cross-coupling polycondensation of thiophene derivatives occurs via C-S bond cleavage in the presence of a nickel catalyst. Head to tail type (HT) regioregular poly(3-hexylthiophene) is obtained by a nickel(II)-catalyzed deprotonative C-H functionalization polycondensation of 2-(phenylsulfonyl)-3-hexylthiophene with stoichiometric TMPMgCl center dot LiCl or with the catalytic secondary amine/RMgX. Debrominative Grignard metathesis (GRIM) polymerization with 5-bromo-2-(phenylsulfonyl)-3-hexylthiophene also proceeds by the catalysis of the nickel(II) complex to afford the corresponding polythiophene.

  DOI：

  10.1021/om4010737

文献信息

• Nickel(II)-Catalyzed Cross-Coupling Polycondensation of Thiophenes via C–S Bond Cleavage
  作者：Shunsuke Tamba、Kanta Fuji、Karin Nakamura、Atsunori Mori

  DOI：10.1021/om4010737

  日期：2014.1.13

  Cross-coupling polycondensation of thiophene derivatives occurs via C-S bond cleavage in the presence of a nickel catalyst. Head to tail type (HT) regioregular poly(3-hexylthiophene) is obtained by a nickel(II)-catalyzed deprotonative C-H functionalization polycondensation of 2-(phenylsulfonyl)-3-hexylthiophene with stoichiometric TMPMgCl center dot LiCl or with the catalytic secondary amine/RMgX. Debrominative Grignard metathesis (GRIM) polymerization with 5-bromo-2-(phenylsulfonyl)-3-hexylthiophene also proceeds by the catalysis of the nickel(II) complex to afford the corresponding polythiophene.