(E)-N-tert-butyl-5-methyl-2-styrylbenzofuran-3-amine | 1610629-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (E)-N-tert-butyl-5-methyl-2-styrylbenzofuran-3-amine
• 英文别名: N-tert-butyl-5-methyl-2-[(E)-2-phenylethenyl]-1-benzofuran-3-amine
• CAS: 1610629-16-7
• 化学式: C₂₁H₂₃NO
• 分子量: 305.42
• InChiKey: KQFZNJYUAQIYAX-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-bromo-3-phenylprop-2-yne 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 29.0h， 生成 (E)-N-tert-butyl-5-methyl-2-styrylbenzofuran-3-amine 、 N-tert-butyl-5-methyl-2-[(Z)-2-styryl]-1-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

文献信息

• Base-mediated intramolecular cyclization of (2-propargyl ether) arylimines: an approach to 3-amino-benzofurans
  作者：Rafaela Gai、Thaís Prochnow、Davi F. Back、Gilson Zeni

  DOI：10.1016/j.tet.2014.04.053

  日期：2014.6

  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.