2,2'-bis(4-methylphenylethynyl)diphenylacetylene | 1048971-97-6

• 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: 2,2'-bis(4-methylphenylethynyl)diphenylacetylene
• 英文别名: 1-Methyl-4-[2-[2-[2-[2-[2-(4-methylphenyl)ethynyl]phenyl]ethynyl]phenyl]ethynyl]benzene
• CAS: 1048971-97-6
• 化学式: C₃₂H₂₂
• 分子量: 406.527
• InChiKey: YBJCGZKVXNIWFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,2'-bis(4-methylphenylethynyl)diphenylacetylene 在 偶氮二异丁腈 、 三正丁基氢锡 、 盐酸 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到13-methyl-1-(4-methylphenyl)-1,6-dihydrobenzo[a]indeno[2,1-c]fluorene
  参考文献：
  名称：

  Radical Cascade Transformations of Tris(o-aryleneethynylenes) into Substituted Benzo[a]indeno[2,1-c]fluorenes

  摘要：

  Oligomeric o-aryleneethynylenes with three triple bonds undergo cascade radical transformations in reaction with a Bu3SnH/AlBN system. These cascades involve three consecutive cycle closures with the formation of substituted benzo[a]indeno[2,1-c]fluorene or benzo[1,2]fluoreno[4,3-b]silole derivatives. The success of this sequence depends on regioselectivity of the initial attack of the Bu3Sn radical at the central triple bond of the o-aryleneethynylene moiety. The cascade is propagated through the sequence of 5-exo-dig and 6-exo-dig cyclizations which is followed by either a radical attack at the terminal Ar substituent or radical transposition which involves H-abstraction from the terminal TMS group and 5-endo-trig cyclization. Overall, the transformation has potential to be developed into an approach to a new type of graphite ribbons.

  DOI：

  10.1021/ja8038213
• 作为产物：
  描述：

  4-碘甲苯 、 双(2-乙炔基苯基)乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以53%的产率得到2,2'-bis(4-methylphenylethynyl)diphenylacetylene
  参考文献：
  名称：

  Radical Cascade Transformations of Tris(o-aryleneethynylenes) into Substituted Benzo[a]indeno[2,1-c]fluorenes

  摘要：

  Oligomeric o-aryleneethynylenes with three triple bonds undergo cascade radical transformations in reaction with a Bu3SnH/AlBN system. These cascades involve three consecutive cycle closures with the formation of substituted benzo[a]indeno[2,1-c]fluorene or benzo[1,2]fluoreno[4,3-b]silole derivatives. The success of this sequence depends on regioselectivity of the initial attack of the Bu3Sn radical at the central triple bond of the o-aryleneethynylene moiety. The cascade is propagated through the sequence of 5-exo-dig and 6-exo-dig cyclizations which is followed by either a radical attack at the terminal Ar substituent or radical transposition which involves H-abstraction from the terminal TMS group and 5-endo-trig cyclization. Overall, the transformation has potential to be developed into an approach to a new type of graphite ribbons.

  DOI：

  10.1021/ja8038213

文献信息

• Radical Cascade Transformations of Tris(<i>o</i>-aryleneethynylenes) into Substituted Benzo[<i>a</i>]indeno[2,1-<i>c</i>]fluorenes
  作者：Igor V. Alabugin、Kerry Gilmore、Satish Patil、Mariappan Manoharan、Serguei V. Kovalenko、Ronald J. Clark、Ion Ghiviriga

  DOI：10.1021/ja8038213

  日期：2008.8.27

  Oligomeric o-aryleneethynylenes with three triple bonds undergo cascade radical transformations in reaction with a Bu3SnH/AlBN system. These cascades involve three consecutive cycle closures with the formation of substituted benzo[a]indeno[2,1-c]fluorene or benzo[1,2]fluoreno[4,3-b]silole derivatives. The success of this sequence depends on regioselectivity of the initial attack of the Bu3Sn radical at the central triple bond of the o-aryleneethynylene moiety. The cascade is propagated through the sequence of 5-exo-dig and 6-exo-dig cyclizations which is followed by either a radical attack at the terminal Ar substituent or radical transposition which involves H-abstraction from the terminal TMS group and 5-endo-trig cyclization. Overall, the transformation has potential to be developed into an approach to a new type of graphite ribbons.