(4-Methoxy-5-methyl-2-phenylnaphthalen-1-yl) acetate | 1187096-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4-Methoxy-5-methyl-2-phenylnaphthalen-1-yl) acetate
• CAS: 1187096-49-6
• 化学式: C₂₀H₁₈O₃
• 分子量: 306.361
• InChiKey: KHVMTQUYEVPCAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-Methoxy-5-methyl-2-phenylnaphthalen-1-yl) acetate 在 aluminum (III) chloride 、 丙烷-1-硫醇 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  Optically Active (aR)- and (aS)-Linear and Vaulted Biaryl Ligands: Deracemization versus Oxidative Dimerization

  摘要：

  The copper-mediated deracemization of the C2-symmetric vaulted biaryl ligands VANOL and VAPOL has been investigated. In the course of the studies that have led to a more reliable procedure for this process, an unprecedented oxidative dimerization of these ligands has been uncovered. The structures of these oxidative dimerization products were elucidated by a series of NMR experiments, and these assignments were supported by other spectroscopic techniques as well as their chemical reactivity. This oxidative dimerization process was not observed for the linear biaryl ligands BANOL and BINOL, although the new deracemization procedure was effective for the generation of BINOL with high optical purity. The (aS)-enantiomers of BINOL, VANOL and VAPOL were accessible with a copper complex of (-)-sparteine, and the (aR)-enantiomeric series were accessible with a copper complex of O'Brien's diamine. Both sparteine and O'Brien's diamine give higher optical purities with VANOL and VAPOL than with BINOL, and this is consistent with the steric congestion present in the matched and mismatched copper complexes of these diamines with the biaryl ligands.

  DOI：

  10.1021/ja903820m
• 作为产物：
  描述：

  [(2-methylphenyl)(methoxy)methylene]pentacarbonylchromium(0) 、 乙酸酐 、 苯乙炔 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以61%的产率得到(4-Methoxy-5-methyl-2-phenylnaphthalen-1-yl) acetate
  参考文献：
  名称：

  Optically Active (aR)- and (aS)-Linear and Vaulted Biaryl Ligands: Deracemization versus Oxidative Dimerization

  摘要：

  The copper-mediated deracemization of the C2-symmetric vaulted biaryl ligands VANOL and VAPOL has been investigated. In the course of the studies that have led to a more reliable procedure for this process, an unprecedented oxidative dimerization of these ligands has been uncovered. The structures of these oxidative dimerization products were elucidated by a series of NMR experiments, and these assignments were supported by other spectroscopic techniques as well as their chemical reactivity. This oxidative dimerization process was not observed for the linear biaryl ligands BANOL and BINOL, although the new deracemization procedure was effective for the generation of BINOL with high optical purity. The (aS)-enantiomers of BINOL, VANOL and VAPOL were accessible with a copper complex of (-)-sparteine, and the (aR)-enantiomeric series were accessible with a copper complex of O'Brien's diamine. Both sparteine and O'Brien's diamine give higher optical purities with VANOL and VAPOL than with BINOL, and this is consistent with the steric congestion present in the matched and mismatched copper complexes of these diamines with the biaryl ligands.

  DOI：

  10.1021/ja903820m