o,o'-bis(p-tolylcarbonyl)-1,2-diphenylacetylene | 1043009-25-1

• 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: o,o'-bis(p-tolylcarbonyl)-1,2-diphenylacetylene
• 英文别名: bis[o-(4-tolylcarbonyl)phenyl]acetylene；[2-[2-[2-(4-Methylbenzoyl)phenyl]ethynyl]phenyl]-(4-methylphenyl)methanone
• CAS: 1043009-25-1
• 化学式: C₃₀H₂₂O₂
• 分子量: 414.503
• InChiKey: ZTUSYYBRGOEPTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  o,o'-bis(p-tolylcarbonyl)-1,2-diphenylacetylene 以 四氢呋喃 为溶剂， 反应 4.0h， 以66%的产率得到3,3'-di(4-tolyl)-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-(4-tolylhydroxymethyl)phenyl]acetylene 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到o,o'-bis(p-tolylcarbonyl)-1,2-diphenylacetylene
  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。
• Photochemical Double 5-<i>exo</i>Cyclization of Alkenyl-Substituted Dithienylacetylenes: Efficient Synthesis of Diarylated Dithienofulvalenes
  作者：Aiko Fukazawa、Takashi Karasawa、Hongyu Zhang、Kazumitsu Minemura、Cristopher Camacho、Jian Wang、Stephan Irle、Shigehiro Yamaguchi

  DOI：10.1002/anie.201303738

  日期：2013.9.27

  Smooth and selective: Upon photoirradiation, bis(3‐alkenyl‐2‐thienyl)acetylenes smoothly and selectively undergo double 5‐exo‐dig cyclization to produce a series of thiophene‐fused pentafulvalenes with various aryl substituents. In this fused π‐conjugated skeleton, the fused thiophene rings and the aryl substituents significantly modulate the electronic structure of the pentafulvalene skeleton.

  平滑的和选择性的：当光照射，双（3-链烯基-2-噻吩基）乙炔平稳且选择性地经历双-5-外-挖环化，以产生一系列具有各种芳基取代基的噻吩稠合pentafulvalenes的。在这个稠合的π共轭骨架中，稠合的噻吩环和芳基取代基显着调节五氟戊烯骨架的电子结构。