2-(2-phenyl-1-naphthyl)oxazoline | 137869-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-phenyl-1-naphthyl)oxazoline
• 英文别名: 4,4-dimethyl-2-(2-phenylnaphthalen-1-yl)-5H-1,3-oxazole
• CAS: 137869-15-9
• 化学式: C₂₁H₁₉NO
• 分子量: 301.388
• InChiKey: FYBAXVRVOSQRHM-UHFFFAOYSA-N

物化性质

• 熔点：
  97-99 °C
• 沸点：
  468.7±24.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-phenyl-1-naphthyl)oxazoline 在 sodium tetrahydroborate 、 草酸 、 三氟甲烷磺酸甲酯 作用下， 生成 2-phenyl-1-naphthaldehyde
  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-1-萘甲酸 在 氯化亚砜 、 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 9.0h， 生成 2-(2-phenyl-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.