(E)-2,5-bis[4-(dibutylamino)phenyl]hexa-1,3,5-triene-1,1,6,6-tetracarbonitrile | 1505464-26-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-2,5-bis[4-(dibutylamino)phenyl]hexa-1,3,5-triene-1,1,6,6-tetracarbonitrile
• 英文别名: (3E)-2,5-bis[4-(dibutylamino)phenyl]hexa-1,3,5-triene-1,1,6,6-tetracarbonitrile
• CAS: 1505464-26-5
• 化学式: C₃₈H₄₆N₆
• 分子量: 586.823
• InChiKey: GBQPZHYNSUCQRY-QURGRASLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4-di-n-butylamino)phenylacetylene 、 四氰基乙烯 以 氯仿 为溶剂， 反应 36.0h， 以85%的产率得到(E)-2,5-bis[4-(dibutylamino)phenyl]hexa-1,3,5-triene-1,1,6,6-tetracarbonitrile
  参考文献：
  名称：

  One-Pot Access to Push–Pull Oligoenes by Sequential [2 + 2] Cycloaddition–Retroelectrocyclization Reactions

  摘要：

  The formal [2 + 2] cycloaddition-retroelectrocyclization reaction was employed as the key transformation to obtain donor-substituted, pi-conjugated polycyanohexa-1,3,5-trienes (TCHTs and PCHTs) and polycyanoocta-1,3,5,7-tetraenes from donor-substituted tetracyanobuta-1,3-dienes (TCBDs) and electron-rich alkynes. These push-pull-substituted oligoene chromophores were also accessed in good yield from tetracyanoethylene and donor-substituted alkynes by using a one-pot protocol. All bis-(N,N-dialkylanilino) donor-substituted push-pull trienes and tetraenes showed better electron-accepting potency and lower HOMO-LUMO gaps than the corresponding TCBDs, as evidenced by optical and electrochemical studies.

  DOI：

  10.1021/jo402440m

文献信息

• One-Pot Access to Push–Pull Oligoenes by Sequential [2 + 2] Cycloaddition–Retroelectrocyclization Reactions
  作者：Govindasamy Jayamurugan、Aaron D. Finke、Jean-Paul Gisselbrecht、Corinne Boudon、W. Bernd Schweizer、François Diederich

  DOI：10.1021/jo402440m

  日期：2014.1.3

  The formal [2 + 2] cycloaddition-retroelectrocyclization reaction was employed as the key transformation to obtain donor-substituted, pi-conjugated polycyanohexa-1,3,5-trienes (TCHTs and PCHTs) and polycyanoocta-1,3,5,7-tetraenes from donor-substituted tetracyanobuta-1,3-dienes (TCBDs) and electron-rich alkynes. These push-pull-substituted oligoene chromophores were also accessed in good yield from tetracyanoethylene and donor-substituted alkynes by using a one-pot protocol. All bis-(N,N-dialkylanilino) donor-substituted push-pull trienes and tetraenes showed better electron-accepting potency and lower HOMO-LUMO gaps than the corresponding TCBDs, as evidenced by optical and electrochemical studies.