N,N,N',N'-tetraethyl-4,4'-diaminostilbene | 358778-53-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N,N,N',N'-tetraethyl-4,4'-diaminostilbene
• 英文别名: trans-4,4'-bis(1-diethylamino)stilbene；trans-4,4'-bis(diethylamino)stilbene；(E)-4,4'-bis(diethylamino)stilbene；tetra-N-ethyl-trans-stilbene-4,4'-diyldiamine；Tetra-N-aethyl-trans-stilben-4,4'-diyldiamin；4-[(E)-2-[4-(diethylamino)phenyl]ethenyl]-N,N-diethylaniline
• CAS: 358778-53-7
• 化学式: C₂₂H₃₀N₂
• 分子量: 322.494
• InChiKey: POAWPDHREAUWOY-MDZDMXLPSA-N

物化性质

• 沸点：
  477.9±34.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-二乙基-4-氨基苯甲醛 在 sodium 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以54%的产率得到N,N,N',N'-tetraethyl-4,4'-diaminostilbene
  参考文献：
  名称：

  具有大多光子吸收截面和强双光子诱导蓝色荧光的新型对称取代芪的合成

  摘要：

  高效钛催化还原偶联方法首先被用于合成三种新的生色团，其化学结构已通过红外、1H 核磁共振、质谱和元素分析表征。这些染料溶液表现出约的线性透射率。在 0.005–0.0005 mol dm-3 的浓度下，波长 ≥ 500 nm 时为 90%。由约抽。在 700 nm 激光照射下，它们具有 44.5 × 40-48-62.0 × 10-48 cm4 s 光子-1 的大双光子吸收截面，以及在 437-452 nm 处发生的强上转换蓝色荧光。对于这些染料中的一种，在大约 10 倍的温度下也观察到了 27.3 × 10-76 cm6 s2 光子-1 的大三光子吸收截面。990 nm 激光照射。

  DOI：

  10.1246/bcsj.74.1977

文献信息

• [EN] AZOARYLS AS REVERSIBLY MODULATABLE TUBULIN INHIBITORS<br/>[FR] AZOARYLES UTILISÉS COMME INHIBITEURS RÉVERSIBLEMENT MODULABLES DE TUBULINES
  申请人：ECOLE NORM SUPERIEURE LYON

  公开号：WO2015166295A1

  公开（公告）日：2015-11-05

  The invention concerns a new class of tubulin polymerisation inhibitors and their applications in research and medicine, notably in chemotherapy. The invention proposes new azoaryl derivatives of formula (I): as defined in Claim 1, which may be fully reversibly interconverted between non-tubulin-binding trans and tubulin-binding cis isomeric forms, either by irradiation or spontaneously. The invention also concerns compounds with a azoaryl structure for use in studying the cytoskeleton and/or its associated processes, or in the treatment of a disease for which a tubulin polymerisation inhibition activity has a beneficial effect, wherein the compound is administered to the cell, organism or patient in need of such treatment in the trans form of the diazenyl bond, and where this trans form is inactive as regards a tubulin polymerisation inhibition effect, and where after photoisomerisation in vitro, in cellulo or in vivo to an azoaryl compound in its cis isomeric form of the diazenyl bond by the application of light, optionally with modification in vitro, in cellulo or in vivo of one or more substituents, the resultant cis form is active as regards a tubulin polymerisation inhibition effect.

  这项发明涉及一类新的微管聚合抑制剂及其在研究和医学中的应用，特别是在化疗中。该发明提出了一种新的azoaryl衍生物，其化学式为(I)：如权利要求书中定义的那样，这些衍生物可以在非微管结合的反式和微管结合的顺式异构形式之间完全可逆地相互转化，可以通过辐射或自发转化。该发明还涉及具有azoaryl结构的化合物，用于研究细胞骨架及/或其相关过程，或用于治疗微管聚合抑制活性对某种疾病具有益处的情况，其中该化合物以顺式的偶氮键形式给需要此类治疗的细胞、生物体或患者使用，该顺式形式在微管聚合抑制效应方面是无效的，然后通过光照在体外、细胞内或体内将其光异构化为其顺式偶氮键的顺式异构形式的azoaryl化合物，可选地在体外、细胞内或体内通过修改一个或多个取代基，所得的顺式形式在微管聚合抑制效应方面是有效的。
• Symmetric and asymmetric charge transfer process of two­photon absorbing chromophores: bis­donor substituted stilbenes, and substituted styrylquinolinium and styrylpyridinium derivatives
  作者：XiaoMei Wang、Dong Wang、GuangYong Zhou、WenTao Yu、YuFang Zhou、Qi Fang、MinHua Jiang

  DOI：10.1039/b009769l

  日期：——

  Two-photon absorption properties of a series of symmetrically substituted stilbenes and asymmetrically substituted stilbene-type derivatives with the same conjugated length have been investigated. The effective two-photon absorption cross sections, δTPA, as large as 62.0 × 10−48 cm4 s photon−1 for D-π-D molecules and 48.5 × 10−48 cm4 s photon−1 for D-π-A counterparts have been observed. The effect of these two types of chromophores on the peak position of the linear absorption, one-photon fluorescence as well as two-photon absorptivity is reported. Dipole moment change between the ground and the first excited states (Δµge), and the transition dipole moment between the first and second excited states (Mee′) have also been calculated. It was found that the asymmetrically substituted derivatives possess relatively large Δµge, whereas the symmetrical counterparts show an increase in Mee′. Although a large two-photon absorption resonance is due to the simultaneously high values of Mee′ and Δµge, correlated to intramolecular charge transfer, the former function is larger. These results obtained have demonstrated that the magnitude and the peak position of two-photon absorption depend not only on the amount but also on the direction of the intramolecular charge transfer.

  研究了一系列具有相同共轭长度的对称取代二苯乙烯和不对称取代二苯乙烯类衍生物的双光子吸收特性。观察到 D-π-D 分子的有效双光子吸收截面 δTPA 高达 62.0 × 10-48 cm4 s 光子-1，D-π-A 分子的有效双光子吸收截面 δTPA 高达 48.5 × 10-48 cm4 s 光子-1。报告了这两种发色团对线性吸收峰值位置、单光子荧光以及双光子吸收率的影响。此外，还计算了基态和第一激发态之间的偶极矩变化（Δµge）以及第一激发态和第二激发态之间的过渡偶极矩（Mee′）。结果发现，不对称取代的衍生物具有相对较大的 Δµge，而对称的衍生物则显示出 Mee′ 的增大。虽然较大的双光子吸收共振是由于 Mee′ 和 Δµge 值同时较高所致，但与分子内电荷转移有关，前者的函数较大。这些结果表明，双光子吸收的大小和峰值位置不仅取决于分子内电荷转移的量，还取决于分子内电荷转移的方向。
• 200. The action of tin and hydrochloric acid on p-dialkylaminobenzaldehydes. Part I. The mechanism of the reaction
  作者：Frederick H. C. Stewart

  DOI：10.1039/jr9570001026

  日期：——
• AZOARYLS AS REVERSIBLY MODULATABLE TUBULIN INHIBITORS
  申请人：Ecole Normale Supérieure de Lyon

  公开号：EP3137554A1

  公开（公告）日：2017-03-08
• US6156466A
  申请人：——

  公开号：US6156466A

  公开（公告）日：2000-12-05