4,4'-bis(diphenylmethyl)biphenyl | 22515-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4,4'-bis(diphenylmethyl)biphenyl
• 英文别名: 4,4'-Dibenzhydryl-biphenyl；4.4'-Di-(α-phenyl-benzyl)-biphenyl；1,6-Bis-(diphenylmethyl)-diphenyl；Bis-4,4'-diphenylmethylbiphenyl；4,4'-Bis(diphenylmethyl)-1,1'-biphenyl；1-benzhydryl-4-(4-benzhydrylphenyl)benzene
• CAS: 22515-03-3
• 化学式: C₃₈H₃₀
• 分子量: 486.656
• InChiKey: LOLGQWPPAZJJID-UHFFFAOYSA-N

物化性质

• 沸点：
  616.2±55.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  4,4'-bis(diphenylmethyl)biphenyl 在 二氯化二硫 、 三氯化铝 、 磺酰氯 作用下， 生成 1-[bis(2,3,4,5,6-pentachlorophenyl)methyl]-4-[4-[bis(2,3,4,5,6-pentachlorophenyl)methyl]-2,3,5,6-tetrachlorophenyl]-2,3,5,6-tetrachlorobenzene
  参考文献：
  名称：

  Inert carbon free radicals. I. Perchlorodiphenylmethyl and perchlorotriphenylmethyl radical series

  摘要：

  DOI：

  10.1021/ja00738a021
• 作为产物：
  描述：

  三苯基甲醇 在 硫酸 作用下， 生成 4,4'-bis(diphenylmethyl)biphenyl
  参考文献：
  名称：

  Photolysis of carbocationic species. Triphenylcarbonium ion

  摘要：

  DOI：

  10.1021/ja00752a029

文献信息

• Flash vacuum pyrolysis over magnesium. Part 1. Pyrolysis of benzylic, other aryl/alkyl and aliphatic halides
  作者：R. Alan Aitken、Philip K. G. Hodgson、John J. Morrison、Adebayo O. Oyewale

  DOI：10.1039/b108663d

  日期：2002.1.23

  Flash vacuum pyrolysis over a bed of freshly sublimed magnesium on glass wool results in efficient coupling of benzyl halides to give the corresponding bibenzyls. Where an ortho halogen substituent is present further dehalogenation gives some dihydroanthracene and anthracene. Efficient coupling is also observed for halomethylnaphthalenes and halodiphenylmethanes while chlorotriphenylmethane gives 4,4′-bis(diphenylmethyl)biphenyl. By using α,α′-dihalo-o-xylenes, benzocyclobutenes are obtained in good yield, while the isomeric α,α′-dihalo-p-xylenes give a range of high thermal stability polymers by polymerisation of the initially formed p-xylylenes. Other haloalkylbenzenes undergo largely dehydrohalogenation where this is possible, in some cases resulting in cyclisation. Deoxygenation is also observed with haloalkyl phenyl ketones to give phenylalkynes as well as other products. With simple alkyl halides there is efficient elimination of HCl or HBr to give alkenes. For aliphatic dihalides this also occurs to give dienes but there is also cyclisation to give cycloalkanes and dehalogenation with hydrogen atom transfer to give alkenes in some cases. For 5-bromopent-1-ene the products are those expected from a radical pathway but for 6-bromohex-1-ene they are clearly not. For 2,2-dichloropropane and 1,1-dichloropropane elimination of HCl occurs but for 1,1-dichlorobutane, -pentane and -hexane partial hydrolysis followed by elimination of HCl gives E,E-, E,Z- and Z,Z- isomers of the dialk-1-enyl ethers and fully assigned 13C NMR data are presented for these. With 6-chlorohex-1-yne and 7-chlorohept-1-yne there is cyclisation to give methylenecycloalkanes and -cycloalkynes. The behaviour of 1,2-dibromocyclohexane and 1,2-dichlorocyclooctane under these conditions is also examined. Various pieces of evidence are presented that suggest that these processes do not involve generation of free gas-phase radicals but rather surface-adsorbed organometallic species.

  在玻璃棉上覆盖一层新升华的镁,进行闪式真空热解,能有效促使苄基卤化物耦合生成相应的联苄。当有邻位卤素取代基存在时,进一步脱卤生成部分二氢蒽和蒽。卤甲基萘和二苯基甲烷也能高效耦合,而三苯基氯甲烷则生成4,4′-双(二苯甲基)联苯。用α,α′-二卤代邻二甲苯可以获得较高产率的苯并环丁烯,而异构的α,α′-二卤代对二甲苯,通过形成的对二甲苯的聚合,可以得到一系列高热稳定性的聚合物。其他卤代烃苯大体上会脱卤化氢,某些情况下能产生环化反应。同样可以观察到,苯基卤代烷烃脱去羰基生成苯乙炔以及其他产物。简单的烷基卤化物则高效地脱去HCl或HBr生成烯烃。脂肪族二卤化物也会发生这一反应生成二烯,但不发生环化反应生成环烷烃,或在某些情况下发生氢原子转移的脱卤反应生成烯烃。5-溴戊-1-烯的产物符合自由基途径的预期,但6-溴己-1-烯并不符合。2,2-二氯丙烷和1,1-二氯丙烷能脱去HCl,但1,1-二氯丁烷、戊烷和己烷则能部分水解,随后脱去HCl,生成E,E-, E,Z-和Z,Z-异构体二烷-1-烯基醚,并且得到了这些物质的13C NMR全归属数据。6-氯己-1-炔和7-氯庚-1-炔能发生环化反应生成亚甲基环烷烃和环炔烃。本文还考察了1,2-二溴环己烷和1,2-二氯环辛烷在上述条件下的行为。本文给出了众多种证据,表明这些反应过程不涉及气相自由基的形成,而是表面吸附的金属有机物种。
• Complexation with diol host compounds. Part 10. Synthesis and solid state inclusion properties of bis(diarylhydroxymethyl)-substituted benzenes and biphenyls; X-ray crystal structures of two host polymorphs and of a non-functional host analogue
  作者：Edwin Weber、Konstantions Skobridis、Andreas Wierig、Luigi R. Nassimbeni、Louise Johnson

  DOI：10.1039/p29920002123

  日期：——

  family of host molecules where the molecular axis of usual ‘wheel-and-axle’ compounds is replaced by aromatic units is described. These diol hosts form crystalline inclusions with a variety of uncharged organic molecules mainly of a polar nature (53 different copecies). The formation and stoichimetry depend in a systematic manner on structural parameters of the host allowing these hosts to be more

  描述了一个新的宿主分子家族，其中常用的“轮轴”化合物的分子轴被芳族单元取代。这些二醇主体与主要为极性性质的多种不带电荷的有机分子形成结晶内含物（53种不同的混合物）。形成和化学计量系统地取决于宿主的结构参数，从而使这些宿主比母体化合物更具选择性。非羟基类似物不充当宿主分子。研究了主体化合物2和低效化合物9的两种多晶型物的晶体结构。晶体数据：2（多晶型物α 1），单斜晶，c ^ 2 / Ç，一个＝ 16.827（2），b＝ 15.212（3），c＝ 10.708，β＝ 97.01（1）°，V＝ 2721 3，Z＝ 4；2（多晶型物α 2），三斜晶系，P，一个= 8.807（2），b = 10.687（6），C ^ = 16.263（3）埃，α= 100.97（3）°，β = 91.47（2）°，γ = 113.02（3）°，V = 1375埃3，ž = 2; 9，单斜，P 2 1 / n，a
• Aitken, R. Alan; Hodgson, Philip K. G.; Oyewale, Adebayo O., Chemical Communications, 1997, # 13, p. 1163 - 1164
  作者：Aitken, R. Alan、Hodgson, Philip K. G.、Oyewale, Adebayo O.、Morrison, John J.

  DOI：——

  日期：——
• Tschitschibabin, Chemische Berichte, 1907, vol. 40, p. 1818
  作者：Tschitschibabin

  DOI：——

  日期：——
• Photolysis of carbocationic species. Triphenylcarbonium ion
  作者：E. E. Van Tamelen、Theron M. Cole

  DOI：10.1021/ja00752a029

  日期：1971.11