dimethyl (Z)-2-(3-(dimethylamino)-1,5-bis(4-methoxyphenyl)penta-1,4-diyn-3-yl)maleate | 1233691-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: dimethyl (Z)-2-(3-(dimethylamino)-1,5-bis(4-methoxyphenyl)penta-1,4-diyn-3-yl)maleate
• 英文别名: dimethyl (Z)-2-[3-(dimethylamino)-1,5-bis(4-methoxyphenyl)penta-1,4-diyn-3-yl]but-2-enedioate
• CAS: 1233691-64-9
• 化学式: C₂₇H₂₇NO₆
• 分子量: 461.514
• InChiKey: JUBGZTIIHAMBNB-LYBHJNIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N,N-dimethyl-1,5-bis-(4-methoxyphenyl)penta-1,4-diyn-3-amine 、 丁炔二酸二甲酯 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以75%的产率得到dimethyl (Z)-2-(3-(dimethylamino)-1,5-bis(4-methoxyphenyl)penta-1,4-diyn-3-yl)maleate
  参考文献：
  名称：

  Copper-Catalyzed Coupling Reaction of C−OMe Bonds Adjacent to a Nitrogen Atom with Terminal Alkynes

  摘要：

  The cross coupling of the C-OMe bond adjacent to a nitrogen atom in dialkoxy-N,N-dialkylmethanamines with terminal alkynes was efficiently approached in the presence of copper catalyst under mild conditions to give 3-amino-1,4-diynes in good yields. The reaction is promoted by phosphine ligands and the chemistry provides a simple and efficient route to 3-amino-1,4-diynes. Importantly, the Michael addition occurred with as-prepared 3-amino-1,4-diynes to give the useful Michael-adducts containing tert-alkylamines in a very convenient way. Further studies revealed that (E)-1,5-diarylpent-1-en-4-yn-3-one was formed through the rearrangement by using the neutral alumina column, and the corresponding imine 2-(1,5-diphenylpent-2-en-4-ynylideneamino)ethanol was obtained in the presence of AgOTf.

  DOI：

  10.1021/jo1007898