Ethyl 1,8-bis(dimethylamino)-7-[hydroxy(diphenyl)methyl]naphthalene-2-carboxylate | 936500-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Ethyl 1,8-bis(dimethylamino)-7-[hydroxy(diphenyl)methyl]naphthalene-2-carboxylate
• CAS: 936500-59-3
• 化学式: C₃₀H₃₂N₂O₃
• 分子量: 468.596
• InChiKey: YUYGUOUOAHMVFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 1,8-bis(dimethylamino)-7-[hydroxy(diphenyl)methyl]naphthalene-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以59%的产率得到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：

  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， 生成 Ethyl 1,8-bis(dimethylamino)-7-[hydroxy(diphenyl)methyl]naphthalene-2-carboxylate
  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-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
  作者：Alexander F. Pozharskii、Alexander V. Degtyarev、Oksana V. Ryabtsova、Valery A. Ozeryanskii、Mikhail E. Kletskii、Zoya A. Starikova、Lucjan Sobczyk、Alexander Filarowski

  DOI：10.1021/jo062667v

  日期：2007.4.1

  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.