N-(2-(prop-2-ynyloxy)benzylidene)tert-butylamine | 161095-12-1

• 英文名称: N-(2-(prop-2-ynyloxy)benzylidene)tert-butylamine
• 英文别名: o-(1,2-propynyloxy)benzyl-t-butylimine；N-t-butyl-2-(2-propynyloxy)-benzylideneamine；N-tert-butyl-1-(2-prop-2-ynoxyphenyl)methanimine
• CAS: 161095-12-1
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: UIEQXSAWWCZHCN-UHFFFAOYSA-N

物化性质

• 沸点：
  328.6±27.0 °C(Predicted)
• 密度：
  0.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  N-(2-(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84%的产率得到N-tert-butyl-2-vinylbenzofuran-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：

  水杨醛 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 28.0h， 生成 N-(2-(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

文献信息

• Synthesis of novel bicyclic nitrogen heterocycles by the intramolecular dipolar cycloaddition reaction of nitrones with allenes and alkynes
  作者：Albert Padwa、Michael Meske、Zhijie Ni

  DOI：10.1016/0040-4020(94)00966-x

  日期：1995.1

  formed was identified as 4-methyl-2,5-endo-oxo-2,3,4,5-tetrahydro[1,4]benzoxazepin. The formation of this novel rearranged product involves an initial dipolar cycloaddition across the acetylenic π-bond to give the expected 4-isoxazoline as a transient intermediate. The next step proceeds by homolysis of the O-N linkage and this is followed by ring closure to produce an aziridine which undergoes further

  一系列烯丙基和炔基硝酮的分子内偶极环加成反应的研究已经进行。苯羟胺容易与邻-（1,2-丙二烯氧基）苯甲醛反应生成二氧杂氮杂双环[3.2.1]辛烯。还研究了2-（1,2-丙炔氧基）苯甲醛与N-甲基羟胺的分子内3 + 2-环加成反应。在这种情况下，形成的主要环加合物被鉴定为4-甲基-2,5-内-oxo-2,3,4,5-四氢[1,4]苯并x庚因。这种新颖的重排产物的形成涉及跨越乙炔π键的初始偶极环加成，以产生预期的4-异恶唑啉作为过渡中间体。下一步通过ON键的均质化进行，然后进行环闭合以产生氮丙啶，该氮丙啶经历进一步的CC键裂解。借助于邻-醌甲基化物中间体将所得的甲亚胺叶立德转化为最终的重排产物。还发现苯磺酰基活化的烯与烷基羟胺反应得到硝酮，该硝酮与相邻的π键进行环加成反应，得到所得的双环氮杂环。