3-(4-(dimethylamino)phenyl)buta-1,3-diene-1,1,2,4,4-pentacarbonitrile | 1005420-91-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(4-(dimethylamino)phenyl)buta-1,3-diene-1,1,2,4,4-pentacarbonitrile
• 英文别名: 3-[4-(dimethylamino)phenyl]-1,1,2,4,4-pentacyanobuta-1,3-diene；3-[4-(Dimethylamino)phenyl]buta-1,3-diene-1,1,2,4,4-pentacarbonitrile；3-[4-(dimethylamino)phenyl]buta-1,3-diene-1,1,2,4,4-pentacarbonitrile
• CAS: 1005420-91-6
• 化学式: C₁₇H₁₀N₆
• 分子量: 298.307
• InChiKey: LRVYMKOOHHRQHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-(dimethylamino)phenyl)buta-1,3-diene-1,1,2,4,4-pentacarbonitrile 、 4-二甲基氨基苯乙炔 以 甲苯 为溶剂， 反应 24.0h， 生成 2,4-bis[4-(dimethylamino)phenyl]hexa-1,3,5-triene-1,1,3,6,6-pentacarbonitrile
  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
• 作为产物：
  描述：

  3-(4-(dimethylamino)phenyl)propiolonitrile 、 四氰基乙烯 以 四氢呋喃 为溶剂， 反应 96.0h， 以97%的产率得到3-(4-(dimethylamino)phenyl)buta-1,3-diene-1,1,2,4,4-pentacarbonitrile
  参考文献：
  名称：

  TCNE，TCNQ和F4-TCNQ的[2 + 2]环加成到供体取代的炔炔上，具有有效的分子内电荷转移相互作用的有机超级受体

  摘要：

  竞争最好的一种是：TCNE，TCNQ和F 4 -TCNQ与N进行热[2 + 2]环加成反应，N-二甲基苯胺基取代的氰基炔烃提供了新型的有机超级受体，具有高效的分子内电荷转移相互作用。这些受主在可逆电子吸收和电子亲和力方面都与受主F 4 -TCNQ竞争（见图），这使它们成为p型掺杂剂，在光电器件中有潜在的应用前景。

  DOI：

  10.1002/chem.200802563

文献信息

• New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes
  作者：Philippe Reutenauer、Milan Kivala、Peter D. Jarowski、Corinne Boudon、Jean-Paul Gisselbrecht、Maurice Gross、François Diederich

  DOI：10.1039/b714731g

  日期：——

  Donor-substituted 1,1,2,4,4-pentacyanobuta-1,3-dienes and a cyclohexa-2,5-diene-1,4-diylidene-expanded derivative were prepared by a [2 + 2] cycloaddition of tetracyanoethene (TCNE) or 7,7,8,8-tetracyanoquinodimethane (TCNQ) to anilino-substituted cyanoalkynes, followed by retro-electrocyclisation; they feature intense bathochromically-shifted intramolecular charge-transfer bands and undergo their

  通过四氰基乙烯的[2 + 2]环加成反应制备供体取代的1,1,2,4,4-戊酰基丁-1,3-二烯和环己2,5-二烯-1,4-二亚甲基膨胀的衍生物（TCNE）或7,7,8,8-四氰基喹二甲烷（TCNQ）生成苯胺基取代的氰基炔烃，然后进行逆电环化；它们具有强烈的红移色移的分子内电荷转移带，并以类似于TCNE和TCNQ报道的电势经历其第一单电子还原。
• Expanding the chemical space for push-pull chromophores by non-concerted [2+2] and [4+2] cycloadditions: access to a highly functionalised 6,6-dicyanopentafulvene with an intense, low-energy charge-transfer band
  作者：Govindasamy Jayamurugan、Jean-Paul Gisselbrecht、Corinne Boudon、Franziska Schoenebeck、W. Bernd Schweizer、Bruno Bernet、François Diederich

  DOI：10.1039/c1cc10247h

  日期：——

  [2+2] and [4+2] cycloadditions between N,N-dimethylanilino-substituted 1,1,2,4,4-pentacyanobuta-1,3-diene and 4-ethynyl-N,N-dimethylaniline are controlled by solvent polarity and provide access to a highly functionalised 6,6-dicyanopentafulvene featuring an intense, low-energy charge-transfer band and to an unusual spirocyclic zwitterion, characterised by X-ray analysis.

  N，N-二甲基苯胺基取代的1,1,2,4,4-戊基丁酸-1,3-二烯与4-乙炔基-N，N-二甲基苯胺之间的非一致性[2 + 2]和[4 + 2]环加成它们受溶剂极性的控制，并可以通过具有高强度，低能量的电荷转移带和功能异常的螺环两性离子进行高功能化的6,6-二氰基戊二烯富通，并通过X射线分析对其进行表征。