[4,5-bis(dimethylamino)-1-naphthyl]diphenylmethanol | 309933-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [4,5-bis(dimethylamino)-1-naphthyl]diphenylmethanol
• 英文别名: 4-(alpha-Hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalene；[4,5-bis(dimethylamino)naphthalen-1-yl]-diphenylmethanol
• CAS: 309933-96-8
• 化学式: C₂₇H₂₈N₂O
• 分子量: 396.532
• InChiKey: PZKIBTRNBDWIQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [4,5-bis(dimethylamino)-1-naphthyl]diphenylmethanol 在 盐酸 作用下， 反应 1.0h， 以71%的产率得到4-dimethylamino-11-phenyl-6H,6aH-benzo[a]fluoren-5-one
  参考文献：
  名称：

  peri-Naphthylenediamines

  摘要：

  Tertiary alcohols containing the 4,5-bis(dimethylamino)-1-naphthyl group were synthesized. The carbocations that formed from n-methyl-containing alcohols in an acidic medium underwent smooth E1 elimination to give the corresponding unsaturated derivatives of the "proton sponge" in good yields. At the same time, the carbocation generated from 4-(alpha-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalene was converted into a benzo[a]fluorene derivative as a result of a complex reaction which has been previously unknown in the chemistry of "proton sponges." The structure of the latter derivative was established by X-ray diffraction analysis.

  DOI：

  10.1007/bf02494902
• 作为产物：
  描述：

  4-bromo-1,8-bis(dimethylamino)naphthalene 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 生成 [4,5-bis(dimethylamino)-1-naphthyl]diphenylmethanol
  参考文献：
  名称：

  摘要：

  The 4-deuterio, 4-methyl, 4-iodo, 4-methylthio, 4-trimethylsilyl, and 4-ethoxycarbonyl derivatives of 1,8-bis(dimethylamino)naphthalene ("proton sponge") and some related alcohols were prepared by the reactions of 4,5-bis(dimethylamino)-1-naphthyllithium or 4.5-bis(dimethylamino)-1-naphthylmagnesittm bromide with the corresponding electrophilic reagents. New representatives of double "proton sponges" with the structures of 1,1 ' -binaphthyl ketone and 1,1 ' -binaphthylmethanol were synthesized. The pK(a) values of selected compounds in DMSO were measured by competitive protonation.

  DOI：

  10.1023/a:1011311226664