2-(2-methoxy-4-prop-2-enyl-3,4-dihydronaphthalen-1-yl)-4,4-dimethyl-5H-1,3-oxazole | 137869-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: 2-(2-methoxy-4-prop-2-enyl-3,4-dihydronaphthalen-1-yl)-4,4-dimethyl-5H-1,3-oxazole
• CAS: 137869-08-0
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: UPICXOXPYYCXGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-methoxy-4-prop-2-enyl-3,4-dihydronaphthalen-1-yl)-4,4-dimethyl-5H-1,3-oxazole 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 以62%的产率得到2-(2-methoxy-4-prop-2-enylnaphthalen-1-yl)-4,4-dimethyl-5H-1,3-oxazole
  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
• 作为产物：
  描述：

  2-甲氧基萘-1-甲酰氯 在 正丁基锂 、 氯化亚砜 、 四甲基乙二胺 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 22.0h， 生成 2-(2-methoxy-4-prop-2-enyl-3,4-dihydronaphthalen-1-yl)-4,4-dimethyl-5H-1,3-oxazole
  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