(P,M)-1,11-dimethyl-5,5,7,7-tetraphenyl-5,7-dihydrodibenz[c,e]oxepine | 716337-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: (P,M)-1,11-dimethyl-5,5,7,7-tetraphenyl-5,7-dihydrodibenz[c,e]oxepine
• 英文别名: 1,11-dimethyl-5,5,7,7-tetraphenyl-5,7-dihydrodibenzo[c,e]oxepine；1,11-dimethyl-5,5,7,7-tetraphenylbenzo[d][2]benzoxepine
• CAS: 716337-48-3
• 化学式: C₄₀H₃₂O
• 分子量: 528.693
• InChiKey: YDGXMBXFZMBTAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  41
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (P,M)-1,11-dimethyl-5,5,7,7-tetraphenyl-5,7-dihydrodibenz[c,e]oxepine 在 trimethylsilyl perchlorate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 以97%的产率得到6,6'-dimethyl-1,1'-biphenyl-2,2'-diylbis(diphenylmethylium) diperchlorate
  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：

  dimethyl 6,6'-dimethylbiphenyl-2,2'-dicarboxylate 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (P,M)-1,11-dimethyl-5,5,7,7-tetraphenyl-5,7-dihydrodibenz[c,e]oxepine
  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

• (<i>P</i>,<i>M</i>)-1,2,3,9,10,11-Hexamethoxy-5,7-dihydrodibenz[<i>c</i>,<i>e</i>]oxepine and (<i>P</i>,<i>M</i>)-1,11-dimethyl-5,5,7,7-tetraphenyl-5,7-dihydrodibenz[<i>c</i>,<i>e</i>]oxepine
  作者：Anthony Linden、Markus Furegati、Andreas J. Rippert

  DOI：10.1107/s010827010400294x

  日期：2004.4.15

  The title compounds, C20H24O7 and C40H32O, respectively, are racemic oxepines, the molecules of which contain a chiral axis. Both molecules possess crystallographic C-2 symmetry and the seven-membered ring adopts a twisted-boat conformation.
• 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.