bis[o-(phenylcarbonyl)phenyl]acetylene | 1043009-23-9

• 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: bis[o-(phenylcarbonyl)phenyl]acetylene
• 英文别名: [2-[2-(2-Benzoylphenyl)ethynyl]phenyl]-phenylmethanone
• CAS: 1043009-23-9
• 化学式: C₂₈H₁₈O₂
• 分子量: 386.45
• InChiKey: BFQMZBIWHGBIMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis[o-(phenylcarbonyl)phenyl]acetylene 以 四氢呋喃 为溶剂， 反应 4.0h， 以90%的产率得到3,3'-diphenyl-1,1'-bi(isobenzofuran)
  参考文献：
  名称：

  Highly Electron-Donating 3,3′-Diaryl-1,1′-bi(isobenzofuran)s Synthesized by Photochemical Exocyclic [2 + 2 + 2] Cycloaddition

  摘要：

  Facile photochemical exocyclic [2 + 2 + 2] cycloaddition produced a series of electron-donating 1,1'-bi(isobenzofuran)s having various aryl groups at the 3,3' positions. The 1,1'-bi(isobenzofuran) skeleton with a highly coplanar structure is a useful building unit to construct the narrow bandgap pi-conjugated systems with low oxidation potentials.

  DOI：

  10.1021/ol801358c
• 作为产物：
  描述：

  bis[o-(phenylhydroxymethyl)phenyl]acetylene 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以93%的产率得到bis[o-(phenylcarbonyl)phenyl]acetylene
  参考文献：
  名称：

  Highly Electron-Donating 3,3′-Diaryl-1,1′-bi(isobenzofuran)s Synthesized by Photochemical Exocyclic [2 + 2 + 2] Cycloaddition

  摘要：

  Facile photochemical exocyclic [2 + 2 + 2] cycloaddition produced a series of electron-donating 1,1'-bi(isobenzofuran)s having various aryl groups at the 3,3' positions. The 1,1'-bi(isobenzofuran) skeleton with a highly coplanar structure is a useful building unit to construct the narrow bandgap pi-conjugated systems with low oxidation potentials.

  DOI：

  10.1021/ol801358c

文献信息

• Intramolecular Reductive Double Cyclization of <i>o</i>,<i>o</i>′-Bis(arylcarbonyl)diphenylacetylenes: Synthesis of Ladder π-Conjugated Skeletons
  作者：Hongyu Zhang、Takashi Karasawa、Hiroshi Yamada、Atsushi Wakamiya、Shigehiro Yamaguchi

  DOI：10.1021/ol901148p

  日期：2009.7.16

  reduction dominantly occurs over the acetylene reduction. The produced bis(radical anion) intermediate undergoes a synchronous double-radical 5-endo-dig cyclization. This simple reduction procedure produces two intriguing classes of ladder π-conjugated skeletons, i.e., emissive methylene-bridged stilbenes and dibenzo[a,e]pentalenes regarded as a cyclic 1,4-diphenylbutadiene.

  用萘二甲酸锂处理双（芳基羰基）二苯基乙炔时，羰基还原反应主要发生在乙炔还原反应之上。产生的双（自由基阴离子）中间体经历同步的双自由基5-内切-挖掘环化。这种简单的还原过程产生了两个有趣的梯形π共轭骨架，即被认为是环状1,4-二苯基丁二烯的亚甲基桥联发光苯乙烯和二苯并[ a，e ]戊烯。