3-bromo-2-(3-cyanophenyl)benzo[b]thiophene | 1403935-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-bromo-2-(3-cyanophenyl)benzo[b]thiophene
• 英文别名: 3-(3-Bromo-1-benzothiophen-2-yl)benzonitrile；3-(3-bromo-1-benzothiophen-2-yl)benzonitrile
• CAS: 1403935-18-1
• 化学式: C₁₅H₈BrNS
• 分子量: 314.205
• InChiKey: RCKUPLUYGDTWHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-2-(3-cyanophenyl)benzo[b]thiophene 在 sodium tetrahydroborate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以95%的产率得到2-(3-cyanophenyl)-benzo[b]thiophene
  参考文献：
  名称：

  Room-Temperature Hydrodehalogenation of Halogenated Heteropentalenes with One or Two Heteroatoms

  摘要：

  The pair NaBH4-TMEDA as a hydride source and catalytic PdCl2(4ppf) in THF prove to be an efficient system for the hydrodehalogenation of bromo(chloro)-heteropentalenes. with one or two heteroatoms, while Pd(OAc)(2)/PPh3 is able to reduce reactive haloheteropentalenes, and PdCl2(tbpf) allows the removal of the 2-chlorine from a thiophene ring. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene, and nitrile substituents and also showing good efficiency in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.

  DOI：

  10.1021/jo3019335
• 作为产物：
  描述：

  2,3-二溴苯并[b]噻吩 、 3-cyanophenylboronic acid MIDA ester 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以76%的产率得到3-bromo-2-(3-cyanophenyl)benzo[b]thiophene
  参考文献：
  名称：

  Room-Temperature Hydrodehalogenation of Halogenated Heteropentalenes with One or Two Heteroatoms

  摘要：

  The pair NaBH4-TMEDA as a hydride source and catalytic PdCl2(4ppf) in THF prove to be an efficient system for the hydrodehalogenation of bromo(chloro)-heteropentalenes. with one or two heteroatoms, while Pd(OAc)(2)/PPh3 is able to reduce reactive haloheteropentalenes, and PdCl2(tbpf) allows the removal of the 2-chlorine from a thiophene ring. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene, and nitrile substituents and also showing good efficiency in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.

  DOI：

  10.1021/jo3019335