4-ethylamino-3,4-dihydro-8-methoxy-3-methylene-2H-1-benzopyran | 1276664-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-ethylamino-3,4-dihydro-8-methoxy-3-methylene-2H-1-benzopyran
• 英文别名: N-ethyl-8-methoxy-3-methylidene-4H-chromen-4-amine
• CAS: 1276664-90-4
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: KYZDJLLYYWDISU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二乙胺 、 3-甲氧基-2-(2-丙炔-1-基氧基)苯甲醛 在 copper(l) iodide 、 三环己基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以74%的产率得到4-ethylamino-3,4-dihydro-8-methoxy-3-methylene-2H-1-benzopyran
  参考文献：
  名称：

  Intramolecular iminium ene reaction with Cu(I) catalysts: facile formation of 4-amino-3-methylenechromans from O-propargyl salicylaldehydes and dialkylamines

  摘要：

  Reaction of O-propargyl salicylaldehyde and related compounds with dialkylamines in the presence of copper(I) iodide gave 4-(alkylamino)-3-methylenechroman derivatives in good yields through the loss of one alkyl group of the dialkylamine. The reaction also worked well by employing 2-amino benzaldehyde derivatives to afford 4-(alkylamino)-3-methylene-1,2,3,4-tetrahydroquinolines. A deuterium-labeling experiment suggested that the a-hydrogen of the dialkylamine was transferred intramolecularly into the terminal methylene. This result indicated the reaction mechanism, which involved the formation of iminium ion between the aldehyde and the dialkylamine followed by ene-type C-C bond formation with inverse electron demand and hydrolysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.007

文献信息

• Intramolecular iminium ene reaction with Cu(I) catalysts: facile formation of 4-amino-3-methylenechromans from O-propargyl salicylaldehydes and dialkylamines
  作者：Noriyoshi Arai、Takeshi Ohkuma

  DOI：10.1016/j.tet.2011.01.007

  日期：2011.3

  Reaction of O-propargyl salicylaldehyde and related compounds with dialkylamines in the presence of copper(I) iodide gave 4-(alkylamino)-3-methylenechroman derivatives in good yields through the loss of one alkyl group of the dialkylamine. The reaction also worked well by employing 2-amino benzaldehyde derivatives to afford 4-(alkylamino)-3-methylene-1,2,3,4-tetrahydroquinolines. A deuterium-labeling experiment suggested that the a-hydrogen of the dialkylamine was transferred intramolecularly into the terminal methylene. This result indicated the reaction mechanism, which involved the formation of iminium ion between the aldehyde and the dialkylamine followed by ene-type C-C bond formation with inverse electron demand and hydrolysis. (C) 2011 Elsevier Ltd. All rights reserved.