1,1,3,3-tetraphenyl-1H,3H-benzo[d,e]isochromene | 105583-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1,3,3-tetraphenyl-1H,3H-benzo[d,e]isochromene
• 英文别名: 2,2,4,4-Tetraphenyl-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene
• CAS: 105583-88-8
• 化学式: C₃₆H₂₆O
• 分子量: 474.602
• InChiKey: JFXIMGSZPFVEEL-UHFFFAOYSA-N

物化性质

• 熔点：
  244-245 °C(Solv: dichloromethane (75-09-2); methanol (67-56-1))
• 沸点：
  618.4±24.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  37
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1,3,3-tetraphenyl-1H,3H-benzo[d,e]isochromene 在 trimethylsilyl perchlorate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以95%的产率得到naphthalene-1,8-diylbis(diphenylmethylium) diperchlorate
  参考文献：
  名称：

  1,8-Bis(diphenylmethylium)naphthalenediyl Dication as an Organic Oxidant:  Synthesis of Benzidines via Self-Coupling of N,N-Dialkylanilines

  摘要：

  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.

  DOI：

  10.1021/ol048058w
• 作为产物：
  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

文献信息

• 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.