1,2,3,4,5-Penta(4-methylphenyl)-1,3-cyclopentadiene | 145828-78-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2,3,4,5-Penta(4-methylphenyl)-1,3-cyclopentadiene
• 英文别名: 1-Methyl-4-[2,3,4,5-tetrakis(4-methylphenyl)cyclopenta-1,4-dien-1-yl]benzene
• CAS: 145828-78-0
• 化学式: C₄₀H₃₆
• 分子量: 516.726
• InChiKey: DPVQZVNOBMHZQK-UHFFFAOYSA-N

物化性质

• 沸点：
  647.1±55.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  1,2,3,4,5-Penta(4-methylphenyl)-1,3-cyclopentadiene 在 10% palladium on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 以86%的产率得到(3R*,4S*,5S*)-1,2,3,4,5-pentakis(4-methylphenyl)cyclopentene
  参考文献：
  名称：

  五苯基环戊二烯和五苯基环戊烯的加氢和脱氢

  摘要：

  五芳基取代的环戊二烯和环戊烯已被用于催化加氢和光化学环脱氢反应，针对应变碗状结构。两种类型的反应通常分别在单加氢和单环化阶段停止。

  DOI：

  10.1002/ejoc.201000821
• 作为产物：
  描述：

  对溴甲苯 、 环戊二烯 在 palladium diacetate 三叔丁基膦 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以87%的产率得到1,2,3,4,5-Penta(4-methylphenyl)-1,3-cyclopentadiene
  参考文献：
  名称：

  Palladium-Catalyzed Arylation of Cyclopentadienes

  摘要：

  Cyclopentadiene and metallocenes, typically zirconocene dichloride, are suitable substrates for multiple arylations with aryl bromides in palladium-catalyzed reactions. Thus, various aryl bromides bearing either an electron-donating or an electron-withdrawing substituent can react with these substrates to afford the corresponding 1,2,3,4,5-pentaaryl-13-cyclopentadienes in a single preparative step. Derivatives of cyclopentadiene. including di- and trisubstituted cyclopentadienes. and indene are arylated in a similar fashion.

  DOI：

  10.1002/1521-3765(20000915)6:18<3426::aid-chem3426>3.0.co;2-b

文献信息

• Palladium-catalysed reaction of aryl bromides with metallocenes to produce pentaarylated cyclopentadienes
  作者：Masahiro Miura、Sommai Pivsa-Art、Tetsuya Satoh、Masakatsu Nomura、Masahiro Miura、Gerald Dyker、Jörg Heiermann

  DOI：10.1039/a804026e

  日期：——

  Aryl bromides can efficiently react with some metallocenes, typically zirconocene dichloride, in the presence of a palladium/phosphine catalyst system and an appropriate base to produce the corresponding pentaarylated cyclopentadienes.

  在钯/膦催化剂体系和适当碱的存在下，芳基溴化物可以有效地与某些茂金属（通常是二氯化锆）发生反应，生成相应的五芳基化环戊二烯。
• The preparation of mixed ligand ruthenocenes containing bulky cyclopentadienyl ligands. Crystal structures of pentaphenylruthenocene, [Ru(η5-C5Ph5)(η5-C5H5)], pentaparatolylruthenocene, [Ru{η5-C5(p-MeC6H4)5}(η5-C5H5)] and pentaphenylpentamethylruthenocene, [Ru(η5-C5Ph5)(η5-C5Me5)]
  作者：C.U Beck、L.D Field、T.W Hambley、P.A Humphrey、A.F Masters、P Turner

  DOI：10.1016/s0022-328x(98)00622-6

  日期：1998.8

  β=66.43(1), γ=62.80(2)°) were determined by single crystal X-ray diffraction studies; the cyclopentadienyl rings in each structure are almost parallel and nearly eclipsed. For 1, 2 and 3, two oxidative processes, but no reductive electrochemical processes, were observed. The precipitated product from the reaction of Ru3(CO)12, C5Ph5Br and Zn in xylenes yielded, after subsequent reaction with NaBPh4, [

  的混合配位体ruthenocenes的制剂的[Ru（η 5 -C 5 - [R 5）（η 5 -C 5 H ^ 5）] [R 5 =苯基5（1）中，Ph 4 H（2）和（p -MeC 6 ħ 4）5（3）]和[茹（η 5 -C 5博士5）（η 5 -C 5我5）]（4）的报告。的分子结构1（PBCA，一个= 14.234（3），b = 20.276（3），C ^ = 20.625（4）），3（P 1，一个= 19.319（7），b = 21.007（7），C ^ = 10.436（ 3）埃，α = 103.76，β = 95.07（3），γ = 112.59（2）°），4 ·H 2 O（P 1，一个= 12.145（2），b = 12.696（4），C ^ = 14.281 （2）Å，α = 80.41（2），β = 66.43（1），γ通过单晶X射线衍射研究确定= 62.80（2）°；
• Hydrogenation and Dehydrogenation of Pentaphenylcyclopentadienes and Pentaphenylcyclopentenes
  作者：Matthias Kanthak、Enrico Muth、Gerald Dyker

  DOI：10.1002/ejoc.201000821

  日期：2010.11

  Pentaaryl-substituted cyclopentadienes and cyclopentenes have been employed in catalytic hydrogenation and photochemical cyclodehydrogenation reactions, targeting strained bowl-shaped structures. Both types of reactions generally stop at the monohydrogenation and monocyclization stage, respectively.

  五芳基取代的环戊二烯和环戊烯已被用于催化加氢和光化学环脱氢反应，针对应变碗状结构。两种类型的反应通常分别在单加氢和单环化阶段停止。
• Palladium-Catalyzed Arylation of Cyclopentadienes
  作者：Gerald Dyker、Jörg Heiermann、Masahiro Miura、Jun-Ichi Inoh、Sommai Pivsa-Art、Tetsuya Satoh、Masakatsu Nomura

  DOI：10.1002/1521-3765(20000915)6:18<3426::aid-chem3426>3.0.co;2-b

  日期：2000.9.15

  Cyclopentadiene and metallocenes, typically zirconocene dichloride, are suitable substrates for multiple arylations with aryl bromides in palladium-catalyzed reactions. Thus, various aryl bromides bearing either an electron-donating or an electron-withdrawing substituent can react with these substrates to afford the corresponding 1,2,3,4,5-pentaaryl-13-cyclopentadienes in a single preparative step. Derivatives of cyclopentadiene. including di- and trisubstituted cyclopentadienes. and indene are arylated in a similar fashion.