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。
• Organic Super-Acceptors with Efficient Intramolecular Charge-Transfer Interactions by [2+2] Cycloadditions of TCNE, TCNQ, and F₄-TCNQ to Donor-Substituted Cyanoalkynes
  作者：Milan Kivala、Corinne Boudon、Jean-Paul Gisselbrecht、Barbara Enko、Paul Seiler、Imke B. Müller、Nicolle Langer、Peter D. Jarowski、Georg Gescheidt、François Diederich

  DOI：10.1002/chem.200802563

  日期：2009.4.14

  Rivaling the best one: Thermal [2+2] cycloadditions of TCNE, TCNQ, and F4‐TCNQ to N,N‐dimethylanilino‐substituted cyanoalkynes afforded a new class of organic super‐acceptors featuring efficient intramolecular charge‐transfer interactions. These acceptors rival the acceptor F4‐TCNQ in the propensity for reversible electron uptake as well as in electron affinity (see figure), which makes them interesting

  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。
• 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。
• 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.