5-(N,N-Diethylamino)-4-pentadienal | 77226-53-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(N,N-Diethylamino)-4-pentadienal
• 英文别名: 5-(N,N-diethylamino)penta-2,4-dien-1-al；5-(N,N-diethylamino)-2,4-pentadienal；1-Diethylamino-pentadien-(1.3)-al-(5)；5-diethylamino-penta-2,4-dienal；5-Diaethylamino-penta-2,4-dienal；(2E,4E)-5-(diethylamino)penta-2,4-dienal
• CAS: 77226-53-0
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: ZRZCKJONECYVMI-KQQUZDAGSA-N

物化性质

• 沸点：
  239.9±23.0 °C(Predicted)
• 密度：
  0.907±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(N,N-Diethylamino)-4-pentadienal 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙酸酐 为溶剂， 反应 2.0h， 生成 3-dicyanomethylene-2-(5-tetrathiafulvalenyl-2,4-pentadienyliden)-1-indanone
  参考文献：
  名称：

  Tetrathiafulvalene Derivatives as NLO-phores:  Synthesis, Electrochemistry, Raman Spectroscopy, Theoretical Calculations, and NLO Properties of Novel TTF-Derived Donor-π-Acceptor Dyads

  摘要：

  Novel pi -conjugated donor-acceptor chromophores, based on the strong electron-donating tetrathiafulvalene moiety and different electron-withdrawing acceptors, exhibit large second-order optical nonlinearities. The effect of increasing the length of the polyenic spacer and the influence of the nature of the acceptor moiety on the NLO properties have been studied by using the electric field-induced second-harmonic generation (EFISH) technique as well as by semiempirical and ab initio theoretical calculations. A charge-transfer band has been observed in the absorption spectra of these D-pi -A compounds that undergoes an hypsochromic shift when increasing the number of vinylenic spacer units connecting both donor and acceptor moieties. The degree of the intramolecular charge transfer from the donor to the acceptor has also been analyzed by means of Raman spectroscopy.

  DOI：

  10.1021/jo010717k
• 作为产物：
  描述：

  氯化-1-(2,4-二硝基苯基)吡啶嗡盐 、 二乙胺 在 乙醇 作用下， 生成 5-(N,N-Diethylamino)-4-pentadienal
  参考文献：
  名称：

  Knunjanz; Kefeli, Zhurnal Obshchei Khimii, 1945, vol. 15, p. 628,631

  摘要：

  DOI：

文献信息

• A convenient one-step synthesis of formyltetrathiafulvalene vinylogs: Building blocks for new NLO materials
  作者：Mar González、Nazario Matín、JoséL. Segura、Javier Garín、Jesús Orduna

  DOI：10.1016/s0040-4039(98)00467-5

  日期：1998.5

  A new method for the synthesis of formyltetrathiafulvalene vinylogs in which tetrathiafulvalene (TTF) or a substituted derivative of TTF is metalated with lithium diisopropylamide and then reacted with a vinylogous amide to yield the corresponding short polyenals in a one-pot process is described.

  描述了一种合成甲酰基四硫富瓦烯乙烯基酯的新方法，其中将四硫富瓦烯（TTF）或TTF的取代衍生物与二异丙基氨基化锂金属化，然后与一乙烯基酰胺反应，以一锅法生产相应的短多烯。
• Nucleophilic addition of organolithium reagents to cyanine dyes. A new access to functionalized hexatrienes
  作者：Lilia Viteva、Tzveta Gospodova、Yuri Stefanovski、Marie-Rose Mazières、Jean Gérard Wolf

  DOI：10.1016/s0040-4039(01)01672-0

  日期：2001.11

  The possibility for extending a pentamethine carbon chain by the use of an appropriate pair of electrophilic substrates, a cyanine dye- and nucleophilic-organolithium reagent is explored. A new synthetic approach to differently functionalized hexatrienes was achieved as a result of spontaneous or accelerated on silica gel surface Hofmann type elimination of the initially formed adducts. A series of

  探索了通过使用适当的一对亲电子底物，花青染料和亲核有机锂试剂来扩展五甲胺碳链的可能性。由于在硅胶表面上自发形成或加速了霍夫曼型消除了最初形成的加合物，因此获得了一种新的合成方法，用于不同功能化的己三烯。通过用Pd / C和LAH进行两步还原获得了一系列三官能配体。
• Mittel zum Färben von keratinhaltigen Fasern
  申请人：Henkel Kommanditgesellschaft auf Aktien

  公开号：EP0873746A2

  公开（公告）日：1998-10-28

  Es wird ein Mittel zum Färben von keratinhaltigen Fasern, insbesondere menschlichen Haaren, beansprucht, enthaltend Aminovinylaldehyde und/oder -ketone oder deren Derivate an der Carbonylgruppe mit der Formel I oder deren physiologisch verträglichen Salze in der R1 und R2 unabhängig voneinander ein Wasserstoffatom, eine (C1-C4)-Alkylgruppe, Hydroxy-(C1-C4)-alkylgruppe, eine Phenylgruppe, die substituiert sein kann, oder gemeinsam mit dem N-Atom einen heterocyclischen Ring bilden, bedeuten, R3, R4, R5, R6 und R7 für ein Wasserstoffatom, eine (C1-C4)-Alkylgruppe oder ein Halogenatom stehen und n 0, 1 oder 2 bedeutet, wobei R6 und R7 sowie R4 und R6, wenn n gleich 1 ist, jeweils gemeinsam einen Ring bilden können.

  一种用于含角蛋白纤维，特别是人类头发染色的组合物，含有式 I 中羰基上的氨基乙烯基醛和/或酮或其衍生物，或其生理相容盐。 其中 R1 和 R2 各自表示氢原子、(C1-C4)-烷基、羟基-(C1-C4)-烷基、苯基（可被取代）或与 N 原子一起构成杂环、 R3、R4、R5、R6 和 R7 代表氢原子、(C1-C4)-烷基或卤素原子，以及 n 为 0、1 或 2、 其中 R6 和 R7 以及 R4 和 R6（如果 n 为 1）可以各自共同形成一个环。
• A convenient synthetic entry into aldehydes with extended conjugation
  作者：Andrienne C. Friedli、Edward Yang、Seth R. Marder

  DOI：10.1016/s0040-4020(97)00047-1

  日期：1997.2

  Variable-length donor-acceptor polyenes 1-18 were synthesized. In the key step, a polyenal was appended to an aromatic donor through nucleophilic attack oi an organolithium reagent on a vinylogous amide. Yields of aldehydes and dialdehydes in the one-pot process ranged from 12-64% and depended upon number of repeat units (n=1-3) in the polyene chain. (C) 1997 Elsevier Science Ltd.
• Evidence for Two Separate One-Electron Transfer Events in Excited Fulleropyrrolidine Dyads Containing Tetrathiafulvalene (TTF)
  作者：Nazario Martín、Luis Sánchez、M Angeles Herranz、Dirk M. Guldi

  DOI：10.1021/jp9941458

  日期：2000.5.1

  1,3-Dipolar cycloadditions of TTF-azomethine ylides (TTF = tetrathiafulvalene) to C-60 have been used to synthesize a series of novel donor-bridge-acceptor dyads. In these dyads the pyrrolidine[3',4':1,2][60]fullerene is covalently attached to the electron donor TTF either directly (5) or alternatively through one (2a) or two (7) vinyl groups. In the ground state, dyads 2a, 5, and 7 undergo Four quasireversible one-electron reductions and two reversible oxidation steps. The former are associated with the reduction of the C-60 core, whereas the latter correspond to the formation of the radical cation and dication of the TTF moiety, respectively. Semiempirical PM3 calculations reveal donor-acceptor distances of 4.8 Angstrom (5), 7.6 Angstrom (2a), and 10.5 Angstrom (7), and a deviation from planarity between the TTF fragment and the vinylogous spacer. In relation to an N-methylfulleropyrrolidine, the emission of the fullerene singlet excited state in dyads 2a, 5, and 7 is substantially reduced. Furthermore, the fluorescence quantum yield correlates well with the solvent dielectric constant and also with the spatial separation of the donor and acceptor moieties in the dyads. These correlation suggest that intramolecular electron-transfer processes evolving from the fullerene singlet excited state generate the (C-60(.-))-(TTF.+) pair. Pico- and nanosecond-resolved transient spectroscopy further substantiate a rapid transformation of the initially formed singlet excited state into the charge-separated radical pair with intramolecular rates ranging between 1.17 x 10(10) s(-1) and 1.47 x 10(9) s(-1). In all cases, the product of back electron transfer is the triplet excited state, which is generated with markedly high quantum yields (0.61-0.97). The latter is, in addition to the rapid primary intramolecular electron transfer, subject to a slower, secondary intermolecular electron transfer with rate constants of 7 x 10(8) M-1 s(-1) (5) in benzonitrile and 1.6 x 10(9) M-1 s(-1) (5) in toluene.