1,1,2,2-tetraphenylacenaphthene | 815617-41-5

• 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: 1,1,2,2-tetraphenylacenaphthene
• 英文别名: 1,1,2,2-tetraphenyl-1,2-dihydroacenaphthylene；Acenaphthylene, 1,2-dihydro-1,1,2,2-tetraphenyl-；1,1,2,2-tetraphenylacenaphthylene
• CAS: 815617-41-5
• 化学式: C₃₆H₂₆
• 分子量: 458.602
• InChiKey: INQPROZAFMUGPT-UHFFFAOYSA-N

物化性质

• 熔点：
  257-258 °C(Solv: dichloromethane (75-09-2); methanol (67-56-1))
• 沸点：
  496.6±40.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  1,1,2,2-tetraphenylacenaphthene 在 高氯酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 96.0h， 以90%的产率得到1,1,3,3-tetraphenyl-1H,3H-benzo[d,e]isochromene
  参考文献：
  名称：

  Naphthalene-1,8-diylbis(diphenylmethylium) as an Organic Two-Electron Oxidant:  Benzidine Synthesis via Oxidative Self-Coupling of N,N-Dialkylanilines

  摘要：

  Naphthalene-1,8-diylbis(diphenylmethylium) exhibits a unique electron-transfer reduction behavior due to the close proximity of the two triarylmethyl cations, which form a C-C bond while accepting two electrons, leading to 1,1,2,2-tetraphenylacenaphthene. The preparation of the dication was readily accomplished under anhydrous conditions starting from a cyclic bis(triarylmethyl) ether, derived from 1,8-dibromonaphthalene. The process proceeded via deoxygenation accompanying the formation of a disiloxane on treatment with a silylating agent (Me3SiClO4 or Me3SiOTf) in 1,1,1,3,3,3-hexafluoropropan-2-ol. The dication was successfully employed for oxidative coupling of N, N-dialkylanilines at the paraposition to afford the corresponding benzidines in good to excellent yield.

  DOI：

  10.1021/jo060662s
• 作为产物：
  描述：

  1,8-bis(diphenylhydroxymethylium)naphthalenediyl bistetrafluoroborate 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以70%的产率得到1,1,2,2-tetraphenylacenaphthene
  参考文献：
  名称：

  氯化1,8-双（二​​芳基甲基鎓）萘二甲双胍的合成及反应活性。

  摘要：

  [反应：见正文]通过用[HBF4] aq和（CF3CO）2O的混合物处理相应的二醇，制备了1,8-双（双（对-氯苯基）甲基）萘二甲酸酯。甲基中心附近会导致强烈的静电斥力，这种斥力会因吸电子的对氯取代基而加剧。如循环伏安法所示，该指示剂是1,8-双（甲基）萘二烯基系列中最强的氧化剂。它经过氯化物的还原氯化作用，并与溴化物或碘化物反应，得到相应的。

  DOI：

  10.1021/ol0477071

文献信息

• Oxidative Arylation Mediated by Naphthalene-1,8-diylbis(diphenylmethylium): Synthetic Route to Triarylsulfonium Salts
  作者：Hiroyuki Tanabe、Takaharu Kawai、Terunobu Saitoh、Junji Ichikawa

  DOI：10.1246/cl.2010.56

  日期：2010.1.5

  naphthalene-1,8-diylbis(diphenylmethylium), successfully promoted oxidative arylation of the sulfur atom in (4-N,N-dialkylaminophenyl) phenyl sulfides with (4-N,N-dialkylaminopheny)silanes, affording triarylsulfonium salts in good yield.

  双阳离子物质，萘-1,8-二基双（二苯基甲基鎓），成功地促进了（4-N,N-二烷基氨基苯基）苯基硫化物中硫原子与（4-N,N-二烷基氨基苯基）硅烷的氧化芳基化，得到了三芳基锍盐良好的产量。
• 1,8-Bis(diphenylmethylium)naphthalenediyl Dication as an Organic Oxidant:  Synthesis of Benzidines via Self-Coupling of <i>N,N</i>-Dialkylanilines
  作者：Terunobu Saitoh、Suguru Yoshida、Junji Ichikawa

  DOI：10.1021/ol048058w

  日期：2004.11.1

  1,8-Bis(diphenylmethylium)naphthalenediyl dications promoted oxidative coupling of various N,N-dialkylanilines to afford the corresponding para-coupled bisanilines, benzidines, in good to excellent yield. The dications were readily prepared from a cyclic ether precursor, derived from 1,8-dibromonaphthalene, via deoxygenation with a silylating reagent in 1,1,1,3,3,3-hexafluoro-2-propanol under anhydrous conditions.
• Naphthalene-1,8-diylbis(diphenylmethylium) as an Organic Two-Electron Oxidant:  Benzidine Synthesis via Oxidative Self-Coupling of <i>N,N</i>-Dialkylanilines
  作者：Terunobu Saitoh、Suguru Yoshida、Junji Ichikawa

  DOI：10.1021/jo060662s

  日期：2006.8.1

  Naphthalene-1,8-diylbis(diphenylmethylium) exhibits a unique electron-transfer reduction behavior due to the close proximity of the two triarylmethyl cations, which form a C-C bond while accepting two electrons, leading to 1,1,2,2-tetraphenylacenaphthene. The preparation of the dication was readily accomplished under anhydrous conditions starting from a cyclic bis(triarylmethyl) ether, derived from 1,8-dibromonaphthalene. The process proceeded via deoxygenation accompanying the formation of a disiloxane on treatment with a silylating agent (Me3SiClO4 or Me3SiOTf) in 1,1,1,3,3,3-hexafluoropropan-2-ol. The dication was successfully employed for oxidative coupling of N, N-dialkylanilines at the paraposition to afford the corresponding benzidines in good to excellent yield.
• Synthesis and Reactivity of a Chlorinated 1,8-Bis(diarylmethylium)naphthalenediyl Dication
  作者：Huadong Wang、François P. Gabbaï

  DOI：10.1021/ol0477071

  日期：2005.1.1

  8-Bis(bis(p-chlorophenyl)methylium)naphthalenediyl dication has been prepared by treatment of the corresponding diol with a mixture of [HBF4]aq and (CF3CO)2O. The proximity of the methylium centers leads to strong electrostatic repulsions that are exacerbated by the electron-withdrawing p-chloro substituents. As indicated by cyclic voltammetry, this dication is the strongest oxidant of the 1,8-bis(methy

  [反应：见正文]通过用[HBF4] aq和（CF3CO）2O的混合物处理相应的二醇，制备了1,8-双（双（对-氯苯基）甲基）萘二甲酸酯。甲基中心附近会导致强烈的静电斥力，这种斥力会因吸电子的对氯取代基而加剧。如循环伏安法所示，该指示剂是1,8-双（甲基）萘二烯基系列中最强的氧化剂。它经过氯化物的还原氯化作用，并与溴化物或碘化物反应，得到相应的。