1-bromo-2-((R)-sec-butoxy)naphthalene | 1062322-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-bromo-2-((R)-sec-butoxy)naphthalene
• 英文别名: 1-bromo-2-[(2R)-butan-2-yl]oxynaphthalene
• CAS: 1062322-49-9
• 化学式: C₁₄H₁₅BrO
• 分子量: 279.176
• InChiKey: MDTALWKABQUFMC-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  8-喹啉甲腈 、 1-bromo-2-((R)-sec-butoxy)naphthalene 、 碘甲烷 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 N-methyl-1-(8-quinolinyl)-1-(2-(R)-sec-butoxynaphthyl)methylenimine
  参考文献：
  名称：

  Synthesis, separation and structure determination of atropisomeric ketimines: precursors of new potential chiral ligands and phase-transfer catalysts

  摘要：

  Sterically crowded chiral biaryl ketimines have been prepared Via nucleophilic addition onto a substituted benzonitrile or 8-cyanoquinoline and subsequent treatment of the resulting methylenimines either with methyl iodide, or with a chiral primary amine. Atropisomerism due to the hindered rotation of the aryl groups about the C-C bond adjacent to C=N has been evidenced in all cases. Physical separation and full Characterisation (NMR and X-ray analysis) of atropisomeric imines have been accomplished. (C) 2008 Published by Elsevier Ltd

  DOI：

  10.1016/j.tetasy.2008.06.024
• 作为产物：
  描述：

  (S)-(+)-2-丁醇 、 1-溴-2-萘酚 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以94%的产率得到1-bromo-2-((R)-sec-butoxy)naphthalene
  参考文献：
  名称：

  Synthesis, separation and structure determination of atropisomeric ketimines: precursors of new potential chiral ligands and phase-transfer catalysts

  摘要：

  Sterically crowded chiral biaryl ketimines have been prepared Via nucleophilic addition onto a substituted benzonitrile or 8-cyanoquinoline and subsequent treatment of the resulting methylenimines either with methyl iodide, or with a chiral primary amine. Atropisomerism due to the hindered rotation of the aryl groups about the C-C bond adjacent to C=N has been evidenced in all cases. Physical separation and full Characterisation (NMR and X-ray analysis) of atropisomeric imines have been accomplished. (C) 2008 Published by Elsevier Ltd

  DOI：

  10.1016/j.tetasy.2008.06.024