2-bromo-5-styryl-thiophene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-5-styryl-thiophene
• 英文别名: (E)-2-bromo-5-styrylthiophene；trans-Phenyl-2-(5-bromthienyl)-ethylen；5-Brom-2-styrylthiophen；2-bromo-5-[(E)-2-phenylethenyl]thiophene
• 化学式: C₁₂H₉BrS
• 分子量: 265.173
• InChiKey: LUPPXPBBTCDTDR-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-ditosyl-1,5,2,6-dithiadiazocane 、 2-bromo-5-styryl-thiophene 在 甲烷磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以31%的产率得到
  参考文献：
  名称：

  C-和 N-取代的 1,5,2,6-二硫代二氮杂环烷的合成 - 亲电-亲核硫胺化 (ENTA) 试剂

  摘要：

  提出了一种从廉价且负担得起的材料开始形成 S-N 键的合成方法。我们表明，已使用此程序在几个步骤中制备了（未）取代的N保护的环状八元C 2对称次磺酰胺。这些双极性衍生物的合成效用已在各种合成转化中得到证明，这些合成转化可在一个或两个步骤中从简单的起始材料提供具有药物相关性的不同S,N-杂环。

  DOI：

  10.1002/adsc.202100424
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 三苯基苄基溴化膦 在 lithium methanolate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以59%的产率得到2-bromo-5-styryl-thiophene
  参考文献：
  名称：

  α,ω-Distyryl Oligothiophenes:  High Mobility Semiconductors for Environmentally Stable Organic Thin Film Transistors

  摘要：

  Critical to the development of organic electronics is the design and synthesis of new organic semiconductors with improved electrical performance and enhanced environmental stability. We present in this communication the synthesis of a series of simple oligothiophene derivatives that bear the styryl unit as terminal substituent. Thin film field-effect transistors incorporating these compounds show high electrical performance, such as mobilities as high as 0.1 cm2/Vs, along with exceptional stability under ambient conditions. Especially, the longer oligomer, DS-4T, containing the quaterthiophene core gives rise to devices that show no decrease in performance after more than 17 months of storage and under continuous operation. Such stability features are unprecedented in the oligothiophene series.

  DOI：

  10.1021/ja054358c

文献信息

• Dehydrogenative Heck Reaction of Furans and Thiophenes with Styrenes under Mild Conditions and Influence of the Oxidizing Agent on the Reaction Rate
  作者：Alexandre Vasseur、Jacques Muzart、Jean Le Bras

  DOI：10.1002/chem.201101992

  日期：2011.11.4

  CH vs. CBr in Heck: The direct dehydrogenative coupling of furans and thiophenes with styrenes occurs under mild conditions (see scheme). This method allows the coupling of brominated substrates through CH bond activation. In addition, DMSO and benzoquinone had a positive effect on the reaction rate.

  Ç  ħ对丙溴在Heck：呋喃和噻吩与苯乙烯的直接脱氢偶联在温和的条件（参见方案）下发生。该方法允许通过CH键活化来偶联溴化底物。此外，DMSO和苯醌对反应速率有积极影响。
• Synthesis of functionalized thiophenes and oligothiophenes by selective and iterative cross-coupling reactions using indium organometallics
  作者：M. Montserrat Martínez、Miguel Peña-López、José Pérez Sestelo、Luis A. Sarandeses

  DOI：10.1039/c2ob25123j

  日期：——

  The synthesis of unsymmetrical 2,5-disubstituted thiophenes by selective and sequential palladium-catalyzed cross-coupling reactions of indium organometallics with 2,5-dibromothiophene is reported. Following an iterative coupling sequence, α-oligothiophenes were synthesized in good yields and with high atom economy.

  铟有机金属化合物与钯的选择性和顺序钯催化交叉偶联反应合成不对称的2,5-二取代噻吩 2,5-二溴噻吩被报道。按照反复的偶联序列，以高收率和高原子经济性合成了α-低聚噻吩。
• [EN] CYCLOALKENYL-N-HYDROXYUREAS<br/>[FR] CYCLOALCENYL-N-HYDROXYUREES
  申请人：PFIZER PHARMACEUTICALS INC.

  公开号：WO1996016054A1

  公开（公告）日：1996-05-30

  (EN) Certain novel cycloalkenyl-$i(N)-hydroxyurea compounds having the ability to inhibit the 5-lipoxygenase enzyme and having formula (I), and the pharmaceutically acceptable salts thereof, wherein A is selected from optionally substituted phenyl, naphthyl, biphenyl, fluorenyl, furyl, benzo[b]furyl, thienyl, benzo[b]thienyl, pyridyl, quinolyl, indolyl; B is selected from optionally substituted phenylene, furylene, thienylene, pyridylene, thiazolylene, oxazolylene, benzoxazolylene and benzo-thienylene; p is 0, 1 or 2; X is C1-4 alkylene, C2-6 alkenylene, C2-6 alkenylene or the like; Y is selected from hydrogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, C2-6 alkoxyalkoxy, C1-6 alkylthio, OH, halo, cyano and amino; and Z is selected from H and C1-3 alkyl. These compounds are useful in the treatment or alleviation of inflammatory diseases, allergy and cardiovascular diseases in mammals and as the active ingredient in pharmaceutical compositions for treating such conditions.(FR) L'invention concerne certains composés cycloalcényl-$i(N)-hydroxyurée de formule (I) ayant la capacité d'inhiber l'enzyme 5-lipoxygénase, ainsi que leur sels pharmaceutiquement acceptables. Dans la formule (I), A est choisi parmi naphtyle, biphényle, fluorényle, furyle, benzo[b]furyle, thiényle, benzo[b]thiényle, pyridyle, quinolyle, indolyle et phényle éventuellement substitués; B est choisi parmi furylène, thiénylène, pyridylène, thiazolylène, oxazolylène, benzoxazolylène, benzo-thiénylène et phénylène éventuellement substitués; p vaut 0, 1 ou 2; X représente alkylène C1-4, alcénylène C2-6, alcynylène ou similaire; Y est choisi parmi hydrogène, alkyle C1-6, haloalkyle C1-6, alcoxy C2-6, alcoxyalkyle C2-6, alcoxyalcoxy C2-6, alkylthio C1-6, OH, halo, cyano et amino; et Z est choisi parmi H et alkyle C1-3. Ces composés sont utiles dans le traitement ou l'atténuation de maladies inflammatoires, allergiques et cardio-vasculaires chez les mammifères et en tant que principe actif dans des compositions pharmaceutiques destinées à traiter ces états.
• Synthesis of <i>C</i> ‐ and <i>N</i> ‐Substituted 1,5,2,6‐Dithiadiazocanes –Electrophilic‐Nucleophilic Thioamination (ENTA) Reagents
  作者：Tomas Javorskis、Arminas Jurys、Gintautas Bagdžiūnas、Edvinas Orentas

  DOI：10.1002/adsc.202100424

  日期：2021.7

  A synthetic method is presented for S−N bond formation starting from cheap and affordable materials. We show that (un)substituted N-protected cyclic eight-membered C2-symmetric sulfenamides have been prepared in a few steps using this procedure. The synthetic utility of these ambipolar derivatives was demonstrated in a variety of synthetic transformations affording different S,N-heterocyles of pharmaceutical

  提出了一种从廉价且负担得起的材料开始形成 S-N 键的合成方法。我们表明，已使用此程序在几个步骤中制备了（未）取代的N保护的环状八元C 2对称次磺酰胺。这些双极性衍生物的合成效用已在各种合成转化中得到证明，这些合成转化可在一个或两个步骤中从简单的起始材料提供具有药物相关性的不同S,N-杂环。
• α,ω-Distyryl Oligothiophenes:  High Mobility Semiconductors for Environmentally Stable Organic Thin Film Transistors
  作者：Christine Videlot-Ackermann、Jörg Ackermann、Hugues Brisset、Koji Kawamura、Noriyuki Yoshimoto、Pascal Raynal、Ahmed El Kassmi、Frédéric Fages

  DOI：10.1021/ja054358c

  日期：2005.11.30

  Critical to the development of organic electronics is the design and synthesis of new organic semiconductors with improved electrical performance and enhanced environmental stability. We present in this communication the synthesis of a series of simple oligothiophene derivatives that bear the styryl unit as terminal substituent. Thin film field-effect transistors incorporating these compounds show high electrical performance, such as mobilities as high as 0.1 cm2/Vs, along with exceptional stability under ambient conditions. Especially, the longer oligomer, DS-4T, containing the quaterthiophene core gives rise to devices that show no decrease in performance after more than 17 months of storage and under continuous operation. Such stability features are unprecedented in the oligothiophene series.