7-Cyclopenta-2,4-dienylidene-bicyclo[4.2.0]octa-1(6),2,4-triene | 153620-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 7-Cyclopenta-2,4-dienylidene-bicyclo[4.2.0]octa-1(6),2,4-triene
• CAS: 153620-31-6
• 化学式: C₁₃H₁₀
• 分子量: 166.222
• InChiKey: AYYCSBXARSXIKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  7-Cyclopenta-2,4-dienylidene-bicyclo[4.2.0]octa-1(6),2,4-triene 在 氢氧化钾 、 碳酸氢钠 、 溶剂黄146 作用下， 反应 4.5h， 生成 7-Bicyclo[4.2.0]octa-1(6),2,4-trien-7-ylidene-2,3-diaza-bicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Conformational effects on high-spin organic molecules

  摘要：

  The ability of m-phenylene to ferromagnetically couple spin-containing substituents that are substantially twisted out of conjugation is investigated. The ''bis(TMM)'' strategy is employed, in which two triplet TMM biradicals am linked through m-phenylene to produce relatively stable, organic tetraradicals that are characterized by EPR spectroscopy. Under conditions of moderate twisting (4), ferromagnetic coupling is seen, and the tetraradical has a quintet ground state. Severely twisting both TMMs as in 13 disrupts spin communication, and two noninteracting triplets are produced. This is in contrast to other highly twisted m-phenylene derivatives, in which antiferromagnetic coupling has been observed. Surprisingly, severely twisting only one TMM (14) still produces ferromagnetic coupling and a quintet ground state through a spin polarization mechanism analogous to that proposed for 90-degrees twisted ethylene. Several ring-constrained TMMs (17-19) are investigated as models for mom nearly planar systems.

  DOI：

  10.1021/j100152a035
• 作为产物：
  描述：

  苯并环丁烯酮 、 环戊二烯 在 四氢吡咯 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以46%的产率得到7-Cyclopenta-2,4-dienylidene-bicyclo[4.2.0]octa-1(6),2,4-triene
  参考文献：
  名称：

  Conformational effects on high-spin organic molecules

  摘要：

  The ability of m-phenylene to ferromagnetically couple spin-containing substituents that are substantially twisted out of conjugation is investigated. The ''bis(TMM)'' strategy is employed, in which two triplet TMM biradicals am linked through m-phenylene to produce relatively stable, organic tetraradicals that are characterized by EPR spectroscopy. Under conditions of moderate twisting (4), ferromagnetic coupling is seen, and the tetraradical has a quintet ground state. Severely twisting both TMMs as in 13 disrupts spin communication, and two noninteracting triplets are produced. This is in contrast to other highly twisted m-phenylene derivatives, in which antiferromagnetic coupling has been observed. Surprisingly, severely twisting only one TMM (14) still produces ferromagnetic coupling and a quintet ground state through a spin polarization mechanism analogous to that proposed for 90-degrees twisted ethylene. Several ring-constrained TMMs (17-19) are investigated as models for mom nearly planar systems.

  DOI：

  10.1021/j100152a035

文献信息

• Gold-catalysed rearrangement of unconventional cyclopropane-tethered 1,5-enynes
  作者：Rubén Vicente、Eva Tudela、Miguel A. Rodríguez、Ángel L. Suárez-Sobrino、Alfredo Ballesteros

  DOI：10.1039/d2cc02869g

  日期：——

  The synthesis of particular cyclopropane-tethered 1,5-enynes, namely 6-alkynyl-4-alkylidenebicyclo[3.1.0]hex-2-enes, enabled the discovery of unprecedented gold-catalyzed rearrangment to indenes. A computational study of the mechanism of this profound skeleton rearrangement is also disclosed.

  特定环丙烷系链的 1,5-烯炔，即 6-炔基-4-亚烷基双环[3.1.0]hex-2-enes 的合成，使人们能够发现前所未有的金催化重排为茚。还公开了对这种深刻的骨架重排机制的计算研究。