2-<2-(O-methylephedrinyl)-1-naphthyl>oxazoline | 137869-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-<2-(O-methylephedrinyl)-1-naphthyl>oxazoline
• 英文别名: 1-(4,4-dimethyl-5H-oxazol-2-yl)-N-(2-methoxy-1-methyl-2-phenyl-ethyl)-N-methyl-naphthalen-2-amine；1-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-N-(1-methoxy-1-phenylpropan-2-yl)-N-methylnaphthalen-2-amine
• CAS: 137869-18-2
• 化学式: C₂₆H₃₀N₂O₂
• 分子量: 402.536
• InChiKey: CDHFWSOYAGMZTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲氧基-1-萘甲酸 在 正丁基锂 、 氯化亚砜 、 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 11.5h， 生成 2-<2-(O-methylephedrinyl)-1-naphthyl>oxazoline
  参考文献：
  名称：

  Regiospecific synthesis of polysubstituted naphthalenes via oxazoline-mediated nucleophilic aromatic substitutions and additions

  摘要：

  An efficient procedure for the selective functionalization of several positions of 2-methoxynaphthalene is described. Nucleophilic aromatic substitutions were carried out by displacing both a methoxy group and a neutral amine ortho to an oxazoline 6. 4-Substituted naphthalenes 8 were obtained from nucleophilic aromatic addition of an allyllithium species to a position para to the oxazoline 6. The resultant dihydronaphthalenes were converted to the fully aromatic systems 9 or alternatively substituted in the 2-position to form 10. Reductive cleavage of the oxazoline moities in 7 and 9 proceeded smoothly, producing the substituted naphthaldehydes 11.

  DOI：

  10.1021/ja00029a032

文献信息

• Regiospecific synthesis of polysubstituted naphthalenes via oxazoline-mediated nucleophilic aromatic substitutions and additions
  作者：Thomas G. Gant、A. I. Meyers

  DOI：10.1021/ja00029a032

  日期：1992.1

  An efficient procedure for the selective functionalization of several positions of 2-methoxynaphthalene is described. Nucleophilic aromatic substitutions were carried out by displacing both a methoxy group and a neutral amine ortho to an oxazoline 6. 4-Substituted naphthalenes 8 were obtained from nucleophilic aromatic addition of an allyllithium species to a position para to the oxazoline 6. The resultant dihydronaphthalenes were converted to the fully aromatic systems 9 or alternatively substituted in the 2-position to form 10. Reductive cleavage of the oxazoline moities in 7 and 9 proceeded smoothly, producing the substituted naphthaldehydes 11.