N-(2-(3-(naphthalen-2-yl)prop-2-ynyloxy)benzylidene)tert-butylamine | 1610628-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-(3-(naphthalen-2-yl)prop-2-ynyloxy)benzylidene)tert-butylamine
• CAS: 1610628-98-2
• 化学式: C₂₄H₂₃NO
• 分子量: 341.453
• InChiKey: VPRJUQGLHJLHCP-UHFFFAOYSA-N

物化性质

• 熔点：
  62.5-65.5 °C
• 沸点：
  523.2±35.0 °C(predicted)
• 密度：
  0.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2-(3-(naphthalen-2-yl)prop-2-ynyloxy)benzylidene)tert-butylamine 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以60%的产率得到(E)-N-tert-butyl-2-(2-(naphthalen-2-yl)vinyl)benzofuran-3-amine
  参考文献：
  名称：

  Base-mediated intramolecular cyclization of (2-propargyl ether) arylimines: an approach to 3-amino-benzofurans

  摘要：

  We present here a practical synthesis of functional 3-amino-benzofurans through base-promoted intramolecular cyclization of (2-propargyl ether) arylimines. A systematic study of the cyclization system revealed that the presence and the amount of base played an essential role in this reaction. The results showed that the cyclization proceeded cleanly and smoothly under mild reaction conditions, employing potassium tert-butoxide as base, THF as solvent, at room temperature in a short reaction time (1 h). The generality of this reaction has been established with (2-propargyl ether) arylimines having both electron-withdrawing and electron-donating groups. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.053
• 作为产物：
  描述：

  2-(3-bromoprop-1-yn-1-yl)naphthalene 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 28.0h， 生成 N-(2-(3-(naphthalen-2-yl)prop-2-ynyloxy)benzylidene)tert-butylamine
  参考文献：
  名称：

  Base-mediated intramolecular cyclization of (2-propargyl ether) arylimines: an approach to 3-amino-benzofurans

  摘要：

  We present here a practical synthesis of functional 3-amino-benzofurans through base-promoted intramolecular cyclization of (2-propargyl ether) arylimines. A systematic study of the cyclization system revealed that the presence and the amount of base played an essential role in this reaction. The results showed that the cyclization proceeded cleanly and smoothly under mild reaction conditions, employing potassium tert-butoxide as base, THF as solvent, at room temperature in a short reaction time (1 h). The generality of this reaction has been established with (2-propargyl ether) arylimines having both electron-withdrawing and electron-donating groups. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.053