2-bromo-4-(2-(5-bromo-2,4-dimethylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-enyl)-3,5-dimethylthiophene | 1004751-29-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2-bromo-4-(2-(5-bromo-2,4-dimethylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-enyl)-3,5-dimethylthiophene
• 英文别名: 1,2-bis(5'-bromo-2',4'-dimethyl-3'-thienyl)perfluorocyclopentene；2-Bromo-4-[2-(5-bromo-2,4-dimethylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-3,5-dimethylthiophene；2-bromo-4-[2-(5-bromo-2,4-dimethylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-3,5-dimethylthiophene
• CAS: 1004751-29-4
• 化学式: C₁₇H₁₂Br₂F₆S₂
• 分子量: 554.213
• InChiKey: CTFBUSFUSIPTBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-bromo-4-(2-(5-bromo-2,4-dimethylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-enyl)-3,5-dimethylthiophene 在 正丁基锂 、 palladium on activated charcoal 、 氨 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 正己烷 为溶剂， -78.0~20.0 ℃ 、5.07 MPa 条件下， 反应 36.1h， 生成 Boc-Daa(m)
  参考文献：
  名称：

  Development of a new class of photochromic peptides by using diarylethene-based non-natural amino acids

  摘要：

  We synthesized novel photochromic non-natural amino acids based on diarylethene skeletons. The non-natural amino acids can be introduced at any positions in various types of peptides by solid/solution phase synthesis. In this study, linear and cyclic peptides including the diarylethene residues were prepared. Their peptides showed photochromism peculiar to original diarylethenes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.044
• 作为产物：
  描述：

  1,2-bis(2,4-dimethyl-5-trimethylsilyl-3-thienyl)perfluorocyclopentene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到2-bromo-4-(2-(5-bromo-2,4-dimethylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-enyl)-3,5-dimethylthiophene
  参考文献：
  名称：

  A fluorescent photochromic compound for labeling biomolecules

  摘要：

  研究人员开发了一种由二月烯、荧光素和琥珀酰亚胺酯单元组成的荧光光致变色化合物，用于以小分子为基础对生物大分子进行可控荧光标记。

  DOI：

  10.1039/b713663c

文献信息

• Photoswitchable, DNA-Binding Helical Peptides Assembled with Two Independently Designed Sequences for Photoregulation and DNA Recognition
  作者：Kazuhisa Fujimoto、Masaoki Kajino、Ikumi Sakaguchi、Masahiko Inouye

  DOI：10.1002/chem.201201431

  日期：2012.8.6

  Diarylethene‐bridged peptides were developed to photoregulate biomolecular interactions. The peptides are made up of diarylethene‐bridged and DNA‐binding regions at their N‐ and C termini, respectively. The two regions could be independently designed and combined as desired. The α‐helicities of the peptides were photoregulated in on/off or off/on manners, and the manner depended on the positions of two ornithine

  开发了二芳基乙烯桥联的肽来光调节生物分子之间的相互作用。这些肽分别在其N和C末端由二芳基乙烯桥连和DNA结合区域组成。这两个区域可以根据需要独立设计和组合。肽的α-螺旋以开/关或关/开的方式进行光调节，其方式取决于在二芳基乙烯桥连区域发生交联反应的两个鸟氨酸（Orn）残基的位置。在开/关方式下，当二芳基乙烯结构在肽上采用开放形式时，肽会折叠成稳定的α-螺旋。在UV辐射下，二芳基乙烯部分异构化成其封闭形式以使螺旋结构不稳定。石英晶体微天平（QCM）分析表明，与封闭的DNA相比，开放的异构体与目标DNA密切相关。在QCM监测的中间，用荧光灯照射DNA复合物中存在的封闭形式的肽时，频率变化（ΔF）通过二芳基乙烯的光异构化得到增强。
• Thiophene derivatives and polymers thereof
  申请人：RESEARCH DEVELOPMENT CORPORATION OF JAPAN

  公开号：EP0698605A1

  公开（公告）日：1996-02-28

  The present invention provides thiophene derivatives (and a polymer thereof) of the following formula, which will respond to light and electricity and which are best suited for use as photorecording materials and light-electricity conversion elements:    (Where n and m are independent integral numbers greater than 0; R₁ is a hydrogen atom, a halogen atom or a trialkylsilyl group; R₂ are an alkylene group which may possess a substitutent group to form a ring with an ethylenic linkage and a -COOCO- group, respectively, or exclusively a cyno group; and R₃, R₄ and R₅ are a hydrogen atom or an alkyl group, respectively.)

  本发明提供了下式的噻吩衍生物（及其聚合物），它们对光和电都有反应，最适合用作光记录材料和光电转换元件： (其中 n 和 m 是大于 0 的独立整数；R₁ 是氢原子、卤素原子或三烷基硅基；R₂ 是亚烷基，可分别具有一个取代基以形成具有乙烯基连接的环和一个 -COOCO- 基团，或完全是一个炔基；R₃、R₄ 和 R₅ 分别是氢原子或烷基)。
• US5734065A
  申请人：——

  公开号：US5734065A

  公开（公告）日：1998-03-31
• Development of a new class of photochromic peptides by using diarylethene-based non-natural amino acids
  作者：Kazuhisa Fujimoto、Tatsuya Maruyama、Yohei Okada、Tatsuya Itou、Masahiko Inouye

  DOI：10.1016/j.tet.2013.05.044

  日期：2013.7

  We synthesized novel photochromic non-natural amino acids based on diarylethene skeletons. The non-natural amino acids can be introduced at any positions in various types of peptides by solid/solution phase synthesis. In this study, linear and cyclic peptides including the diarylethene residues were prepared. Their peptides showed photochromism peculiar to original diarylethenes. (C) 2013 Elsevier Ltd. All rights reserved.
• A fluorescent photochromic compound for labeling biomolecules
  作者：Nobuaki Soh、Kenji Yoshida、Hizuru Nakajima、Koji Nakano、Toshihiko Imato、Tuyoshi Fukaminato、Masahiro Irie

  DOI：10.1039/b713663c

  日期：——

  A fluorescent photochromic compound, composed of diarylethene, fluorescein and succinimidyl ester units, was developed for the controllable fluorescent labeling of biomolecules based on a small molecule.

  研究人员开发了一种由二月烯、荧光素和琥珀酰亚胺酯单元组成的荧光光致变色化合物，用于以小分子为基础对生物大分子进行可控荧光标记。