(E,E,E)-3-[8-(2,5-dioxo-1-azacyclopent-3-enyl)octyloxy]-4-(2-(benzothiazol-2-yl)vinyl)-N,N-bis(4-(2-(benzothiazol-2-yl)vinyl)phenyl)aniline | 1016164-13-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E,E,E)-3-[8-(2,5-dioxo-1-azacyclopent-3-enyl)octyloxy]-4-(2-(benzothiazol-2-yl)vinyl)-N,N-bis(4-(2-(benzothiazol-2-yl)vinyl)phenyl)aniline
• 英文别名: (3-(8-(2,5-dioxo-1-aza)cyclopent-3-enyl)octyloxy)-{4-[(E)-2-(benzothiazol-2-yl)vinyl]}-N,N-bis-{4-[(E)-2-(benzothiazol-2-yl)vinyl]phenyl}aniline；1-[8-[2-[(E)-2-(1,3-benzothiazol-2-yl)ethenyl]-5-[4-[(E)-2-(1,3-benzothiazol-2-yl)ethenyl]-N-[4-[(E)-2-(1,3-benzothiazol-2-yl)ethenyl]phenyl]anilino]phenoxy]octyl]pyrrole-2,5-dione
• CAS: 1016164-13-8
• 化学式: C₅₇H₄₇N₅O₃S₃
• 分子量: 946.23
• InChiKey: RHMSBWILKFPXIU-JRQATPQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.2
• 重原子数：
  68
• 可旋转键数：
  19
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  173
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  以 苯甲醚 为溶剂， 反应 2.0h， 以11 mg的产率得到(E,E,E)-3-[8-(2,5-dioxo-1-azacyclopent-3-enyl)octyloxy]-4-(2-(benzothiazol-2-yl)vinyl)-N,N-bis(4-(2-(benzothiazol-2-yl)vinyl)phenyl)aniline
  参考文献：
  名称：

  Synthetic Strategies to Derivatizable Triphenylamines Displaying High Two-Photon Absorption

  摘要：

  [Graphics]A versatile synthetic strategy to access a set of highly fluorescent g-conjugated triphenylamines bearing a functional linker at various positions on one phenyl ring is described. These compounds were designed for large two-photon absorption (2PA) and in particular for labeling of biomolecules. The monoderivatized trisformylated or trisiodinated intermediates described herein allow introduction of a large variety of electron-withdrawing groups required for large 2PA as well as a panel of chemical functions suitable for coupling to biomolecules. The monoderivatized three-branched compounds and in particular the benzothiazole JP-3Bz) series show remarkable linear (high extinction coefficients and high quantum yield) and nonlinear (high 2-photon cross sections) optical properties. Interestingly the presence of functional side chains does not disturb the two-photon absorption. Finally, monoderivatized two-branched derivatives also appear to be valuable candidates. Altogether the good optical properties of the new derivatizable pi-conjugated TPA combined with their small size and their compatibility with bioconjugation protocols suggest that they represent a new chemical class of labels potentially applicable for the tracking of biomolecules using two-photon scanning microscopy.

  DOI：

  10.1021/jo702002y

文献信息

• Triphenylamine derivatives useful as fluorophores in biology, in particular for two-photon microscopy
  申请人：Allain Clémence

  公开号：US08664400B2

  公开（公告）日：2014-03-04

  Triphenylamine derivatives useful as fluorophores in biology, in particular for two-photon microscopy; and compositions comprising these derivatives, to the use of these compositions and of the derivatives themselves for labelling biological molecules (or “biomolecules”) such as nucleic acids, oligonucleotides, proteins, polypeptides, plasmids, and the like, for their examination in particular by two-photon microscopy, and to biomolecules labelled with the said derivatives.

  三苯胺衍生物在生物学中作为荧光物质特别有用，特别适用于双光子显微镜；以及包含这些衍生物的组合物，用于标记生物分子（或“生物分子”），如核酸、寡核苷酸、蛋白质、多肽、质粒等，特别是通过双光子显微镜进行检测，并用于标记了上述衍生物的生物分子。
• NOVEL TRIPHENYLAMINE DERIVATIVES USEFUL AS FLUOROPHORES IN BIOLOGY, IN PARTICULAR FOR TWO-PHOTON MICROSCOPY
  申请人：Allain Clémence

  公开号：US20090314990A1

  公开（公告）日：2009-12-24

  Triphenylamine derivatives useful as fluorophores in biology, in particular for two-photon microscopy; and compositions comprising these derivatives, to the use of these compositions and of the derivatives themselves for labelling biological molecules (or “biomolecules”) such as nucleic acids, oligonucleotides, proteins, polypeptides, plasmids, and the like, for their examination in particular by two-photon microscopy, and to biomolecules labelled with the said derivatives.

  三苯胺衍生物在生物学中作为荧光染料特别是用于双光子显微镜的有用性；以及包含这些衍生物的组合物，使用这些组合物和衍生物本身来标记生物分子（或“生物分子”）如核酸、寡核苷酸、蛋白质、多肽、质粒等，特别是通过双光子显微镜对它们进行检测，并且标记有上述衍生物的生物分子。
• NOUVEAUX DERIVES DE LA TRIPHENYLAMINE UTILES COMME FLUOROPHORES EN BIOLOGIE, NOTAMMENT POUR LA MICROSCOPIE BIPHOTONIQUE
  申请人：Commissariat à l'Energie Atomique

  公开号：EP2086937A1

  公开（公告）日：2009-08-12
• US8664400B2
  申请人：——

  公开号：US8664400B2

  公开（公告）日：2014-03-04
• [EN] NOVEL TRIPHENYLAMINE DERIVATIVES FOR USE AS FLUOROPHORES IN BIOLOGY, IN PARTICULAR FOR TWO-PHOTON MICROSCOPY<br/>[FR] NOUVEAUX DERIVES DE LA TRIPHENYLAMINE UTILES COMME FLUOROPHORES EN BIOLOGIE, NOTAMMENT POUR LA MICROSCOPIE BIPHOTONIQUE
  申请人：COMMISSARIAT ENERGIE ATOMIQUE

  公开号：WO2008055969A1

  公开（公告）日：2008-05-15

  [EN] The invention relates to novel triphenylamine derivatives for use as fluorophores, in particular for two-photon microscopy in biology. It also relates to compositions containing these derivatives, to the use of these compositions and also the derivatives themselves for labelling biological molecules (or 'biomolecules') such as nucleic acids, oligonucleotides, proteins, polypeptides, plasmids, etc., with a view to observing them in particular by two-photon microscopy, and to biomolecules labelled with said derivatives. Applications: biological and medical imaging (fundamental research for the structural or functional study of biological systems, applied research for clinical or therapeutic purposes, diagnosis and medical screening, etc.).
  [FR] L'invention se rapporte à de nouveaux dérivés de la triphénylamine utiles comme fluorophores, notamment pour la microscopie biphotonique en biologie. Elle se rapporte également à des compositions contenant ces dérivés, à l'utilisation de ces compositions ainsi que des dérivés eux-mêmes pour le marquage de molécules biologiques (ou "biomolécules") telles que les acides nucléiques, les oligonucléotides, les protéines, les polypeptides, les plasmides, etc, en vue de leur observation notamment par microscopie biphotonique, et à des biomolécules marquées par lesdits dérivés. Applications: imagerie biologique et médicale (recherche fondamentale pour l'étude structurelle ou fonctionnelle des systèmes biologiques, recherche appliquée à visée clinique ou thérapeutique, diagnostic et dépistage médical,...).