2-(α-hydroxybenzhydryl)-7-bromo-1,8-bis(dimethylamino)naphthalene | 852534-33-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-(α-hydroxybenzhydryl)-7-bromo-1,8-bis(dimethylamino)naphthalene
• 英文别名: 1,8-bis(dimethylamino)-7-bromo-2-(α-hydroxybenzhydryl)naphthalene；[7-Bromo-1,8-bis(dimethylamino)naphthalen-2-yl]-diphenylmethanol
• CAS: 852534-33-9
• 化学式: C₂₇H₂₇BrN₂O
• 分子量: 475.428
• InChiKey: IIQDFFIZCZTLAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  31
• 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：

  2-(α-hydroxybenzhydryl)-7-bromo-1,8-bis(dimethylamino)naphthalene 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.0h， 生成 1,8-bis(dimethylamino)-2-(α-hydroxybenzhydryl)-7-hydroxymethylnaphthalene
  参考文献：
  名称：

  2-α-Hydroxyalkyl- and 2,7-Di(α-hydroxyalkyl)-1,8-bis(dimethylamino)naphthalenes:  Stabilization of Nonconventional In/Out Conformers of “Proton Sponges” via N···H−O Intramolecular Hydrogen Bonding. A Remarkable Kind of Tandem Nitrogen Inversion

  摘要：

  A regular set of 2-(alpha-hydroxymethyl)- and 2,7-di(alpha-hydroxymethyl)-1,8-bis(dimethylamino)naphthalenes has been prepared. Their X-ray, NMR, and IR studies have demonstrated that in tertiary mono-alcohols the orientation of free nitrogen electron pairs in crystals and solution corresponds to nonconventional in/out conformers stabilized by O-H center dot center dot center dot N intramolecular hydrogen bonding. For tertiary 2,7-dialcohols, the superimposed equilibrating in/out-out/in nitrogen invertomers are observed in solution. Unlike this, primary and secondary mono- and dialcohols commonly exist in the in/in form, which is typical for the parent proton sponge and the majority of its derivatives.

  DOI：

  10.1021/jo062667v
• 作为产物：
  描述：

  二苯甲酮 、 2,7-dibromo-1,8-bis(dimethylamino)naphthalene 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.17h， 以80%的产率得到2-(α-hydroxybenzhydryl)-7-bromo-1,8-bis(dimethylamino)naphthalene
  参考文献：
  名称：

  2-α-Hydroxyalkyl- and 2,7-Di(α-hydroxyalkyl)-1,8-bis(dimethylamino)naphthalenes:  Stabilization of Nonconventional In/Out Conformers of “Proton Sponges” via N···H−O Intramolecular Hydrogen Bonding. A Remarkable Kind of Tandem Nitrogen Inversion

  摘要：

  A regular set of 2-(alpha-hydroxymethyl)- and 2,7-di(alpha-hydroxymethyl)-1,8-bis(dimethylamino)naphthalenes has been prepared. Their X-ray, NMR, and IR studies have demonstrated that in tertiary mono-alcohols the orientation of free nitrogen electron pairs in crystals and solution corresponds to nonconventional in/out conformers stabilized by O-H center dot center dot center dot N intramolecular hydrogen bonding. For tertiary 2,7-dialcohols, the superimposed equilibrating in/out-out/in nitrogen invertomers are observed in solution. Unlike this, primary and secondary mono- and dialcohols commonly exist in the in/in form, which is typical for the parent proton sponge and the majority of its derivatives.

  DOI：

  10.1021/jo062667v

文献信息

• 2-α-Hydroxybenzhydryl- and 2,7-di(α-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalenes: the first examples of stabilization of in/out proton sponge conformers by intramolecular hydrogen bonding. The most flattened amino group ever participating in IHB
  作者：Alexander F. Pozharskii、Oksana V. Ryabtsova、Valery A. Ozeryanskii、Alexander V. Degtyarev、Zoya A. Starikova、Lucjan Sobczyk、Alexander Filarowski

  DOI：10.1016/j.tetlet.2005.04.045

  日期：2005.6

  2-(alpha-Hydroxybenzhydryl)-6 and 2,7-di(alpha-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalenes 8 have been shown to exist in crystals as in/out conformers stabilized by O-H center dot center dot center dot N intramolecular hydrogen bonding. In agreement with X-ray studies, the NMR data are also consistent with 7 retaining its in/out form in solution, whilst for 8 superimposed equilibrating in/out out/in conformers are observed. (c) 2005 Elsevier Ltd. All rights reserved.