9,9'‐dicyano‐9,9'-bifluorenyl | 24225-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9,9'‐dicyano‐9,9'-bifluorenyl
• 英文别名: 9,9′-dicyano-9,9′-bifluorene；9,9'-dicyano-9,9'-bifluorenyl；[9,9']bifluorenyl-9,9'-dicarbonitrile；[9,9']Bifluorenyl-9,9'-dicarbonitril；9.9'-Dicyan-difluorenyl-(9.9')；9,9'-Dicyano-9,9'-bifluoren；9-(9-Cyanofluoren-9-yl)fluorene-9-carbonitrile
• CAS: 24225-40-9
• 化学式: C₂₈H₁₆N₂
• 分子量: 380.448
• InChiKey: FRRHZMVAQZWLAH-UHFFFAOYSA-N

物化性质

• 熔点：
  268-270 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  583.5±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,9'‐dicyano‐9,9'-bifluorenyl 在 sodium ethanolate 作用下， 生成 9,9'-联芴
  参考文献：
  名称：

  Stolle; Muenzel; Wolf, Chemische Berichte, 1913, vol. 46, p. 2348

  摘要：

  DOI：
• 作为产物：
  描述：

  3,6-di-fluoren-9-ylidene-3,6-dihydro-[1,2,4,5]tetrazine 生成 9,9'‐dicyano‐9,9'-bifluorenyl
  参考文献：
  名称：

  Stolle; Muenzel; Wolf, Chemische Berichte, 1913, vol. 46, p. 2348

  摘要：

  DOI：

文献信息

• Reactions of Trimethylsilyl Cyanide and<i>N</i>-(Trimethylsilyl) diphenylmethyleneamine with Nitrones and Thermal Decompositions of Their Adducts
  作者：Otohiko Tsuge、Satoshi Urano、Takahiko Iwasaki

  DOI：10.1246/bcsj.53.485

  日期：1980.2

  On the other hand, reactions of 1 and 2 with N-(diphenylmethylene)aniline N-oxide or N-(9-fluorenylidene)aniline N-oxide did not give the corresponding 1: 1 adducts, but instead compounds arising from thermal decomposition of initial 1: 1 adducts were directly obtained. The reaction of 1 with N-(p-diethylaminophenyl)-α-phenylnitrone leading to the corresponding α-imino nitrile is also described.

  三甲基甲硅烷基氰化物 (1) 和 N-(三甲基甲硅烷基) 二苯基亚甲基胺 (2) 与 α-芳基-N-苯基-硝酮反应，分别得到相应的 1:1 加合物 4 和 5。4 在回流的二甲苯中热分解得到偶氮苯、2,3-二芳基琥珀腈、α-亚氨基腈和/或苯甲酰苯胺的立体异构体，其产率取决于 4 的苯基上的取代基的性质。在苯中加热 5 得到偶氮苯的混合物和内消旋-N,N'-双(二苯基亚甲基)-1,2-二芳基乙二胺。另一方面，1和2与N-(二苯基亚甲基)苯胺N-氧化物或N-(9-芴基)苯胺N-氧化物的反应没有得到相应的1:1加合物，而是由热分解产生的化合物直接获得初始 1:1 加合物。
• Photochemical generation of 9‐Fluorenyl radicals
  作者：Ian R. Duffy、William J. Leigh、Hanan Afifi、Abdelaziz Ebead、René Fournier、Edward Lee‐Ruff

  DOI：10.1002/poc.3920

  日期：2019.4

  corresponding 9H‐fluorenyl radicals. These transient species were directly observed by laser flash photolysis and their UV/visible spectra compared with those of their corresponding cations. Theoretical calculations (density functional theory [DFT]) of these intermediates indicate their destabilizing nature in similar fashion to the antiaromatic character of the corresponding cations.

  在较少极性的溶剂中辐照一系列9 H-芴醇和9 H，9'H-联芴基，得到由其相应的9 H-芴基自由基衍生的光产物。通过激光闪光光解法直接观察到这些瞬态物质，并将其紫外/可见光谱与其相应阳离子的光谱进行比较。这些中间体的理论计算（密度泛函理论[DFT]）表明，它们的不稳定性质与相应阳离子的抗芳烃特征相似。
• Photochemical Generation of 9H-Fluorenyl Radicals
  作者：Tatiana Dyblenko、Andrei Chtchemelinine、Ryan Reiter、Ruhul Q. Chowdhury、Alexander Enaya、Hanan Afifi、Rene Fournier、Gabriela Mladenova、Alfred Barry P. Lever、Edward Lee-Ruff

  DOI：10.1111/php.12225

  日期：2014.3

  AbstractA series of 9‐substituted fluorenols and 9,9′‐disubstituted‐9,9′‐bifluorenyls were irradiated to give products derived from fluorenyl radicals. Product distribution was solvent dependent. A TEMPO adduct was isolated from the photoexcitation of 9‐fluorenol. An unusual unsymmetrical 3,9′‐bifluorenyl was observed from the photolysis of 9‐trifluoromethylfluorenol and 9,9′‐di(trifluoromethyl)‐9,9′‐bifluorenyl in more polar or hydrogen‐bonding solvents. The electronic nature of 9‐substituted fluorenyl radicals was probed using theoretical calculations showing the dipolar character of species with electron‐deficient groups. These constitute the first examples of “doubly destabilized” radicals.
• TSUGE O.; URANO S.; IWASAKI T., BULL. CHEM. SOC. JAP., 1980, 53, NO 2, 485-489
  作者：TSUGE O.、 URANO S.、 IWASAKI T.

  DOI：——

  日期：——