3-bromo-2-methoxy-4-methyl-5-phenylthiophene | 811830-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromo-2-methoxy-4-methyl-5-phenylthiophene
• 英文别名: 3-Bromo-2-methoxy-4-methyl-5-phenylthiophene
• CAS: 811830-43-0
• 化学式: C₁₂H₁₁BrOS
• 分子量: 283.189
• InChiKey: CFJGRXXJJZBDRO-UHFFFAOYSA-N

物化性质

• 熔点：
  57.8-58.6 °C
• 沸点：
  319.9±37.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-2-methoxy-4-methyl-5-phenylthiophene 在 正丁基锂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 21.5h， 生成 2-(4-ethynylphenyl)-4-(3,3,4,4,5,5-hexafluoro-2-(2-methoxy-4-methyl-5-phenylthiophen-3-yl)cyclopent-1-en-1-yl)-5-methoxy-3-methylthiophene
  参考文献：
  名称：

  Synthesis and characterization of non-symmetrical photoswitchable DTE(OMe) sensitizers

  摘要：

  DTE-BODIPY 2 and BTD-DTE 3 were designed for reversible light modulation of electron- and energy-transfer processes on TiO2, and showed almost complete ring closure. In BTD-DTE 3 the BTD is an acceptor group in the open form (OF), and an energy donor group in the closed form (CF), but this property is depending on the solvent. Quantum yields for ring closure decreased (BTD-DTE 3: factor 5; DTE-BODIPY 2: factor 12) compared to DTE 1, because of it-system elongation in OFs, and also cycloreversion quantum yields became smaller (BTD-DTE 3: factor 1.4; DTE-BODIPY 2: factor 2.2). (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.05.042
• 作为产物：
  描述：

  2-methoxy-4-methylthiophene 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 为溶剂， 反应 10.0h， 生成 3-bromo-2-methoxy-4-methyl-5-phenylthiophene
  参考文献：
  名称：

  Synthesis and characterization of non-symmetrical photoswitchable DTE(OMe) sensitizers

  摘要：

  DTE-BODIPY 2 and BTD-DTE 3 were designed for reversible light modulation of electron- and energy-transfer processes on TiO2, and showed almost complete ring closure. In BTD-DTE 3 the BTD is an acceptor group in the open form (OF), and an energy donor group in the closed form (CF), but this property is depending on the solvent. Quantum yields for ring closure decreased (BTD-DTE 3: factor 5; DTE-BODIPY 2: factor 12) compared to DTE 1, because of it-system elongation in OFs, and also cycloreversion quantum yields became smaller (BTD-DTE 3: factor 1.4; DTE-BODIPY 2: factor 2.2). (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.05.042

文献信息

• 1,3-Bicyclo[1.1.1]pentanediyl: The Shortest Rigid Linear Connector of Phenylated Photochromic Units and a 1,5-Dimethoxy-9,10-di(phenylethynyl)anthracene Fluorophore
  作者：Armin de Meijere、Ligang Zhao、Vladimir N. Belov、Mariano Bossi、Matthias Noltemeyer、Stefan W. Hell

  DOI：10.1002/chem.200601316

  日期：2007.3.16

  3-(4-iodophenyl)bicyclo[1.1.1]pentane, prepared in 63 % yield by iodination of 1,3-diphenylbicyclo[1.1.1]pentane, was selectively mono-coupled with 9-ethynyl-1,5-dimethoxy-10-phenylethynylanthracene (26), and subsequently with the zinc derivatives of 1-(2-methyl/methoxy-4-methyl-5-phenylthiophen-3-yl)-2-(2-methyl/methoxy-4-methylt hiophen-3-yl)perfluorocyclopentenes (38-H-41-H). Regioselective synthesis of the

  将过量的1,3-二苯基双环[1.1.1]戊烷碘化，以63％的收率制得的双1,3-（4-碘苯基）双环[1.1.1]戊烷与9-乙炔基-1,5-二甲氧基-10-苯基乙炔基蒽（26），随后带有1-（2-甲基/甲氧基-4-甲基-5-苯基噻吩-3-基）-2-（2-甲基）的锌衍生物/甲氧基-4-甲基噻吩-3-基）全氟环戊烯（38-H-41-H）。区域选择性合成2-未取代的噻吩38-H-41-H需要中间体制备2-三甲基甲硅烷基-3,5-二甲基-4-溴噻吩（37）或2-三甲基甲硅烷基-5-甲氧基-3-甲基-4-溴噻吩（40）。用2-三甲基甲硅烷基保护噻吩环的α-位可阻止4-硫代衍生物重排成相应的2-锂化的噻吩。与双环[1.1。1]戊烷片段连接光致变色单元1-3和1,5-二甲氧基-9,10-二（苯基乙炔基）蒽作为荧光部分，荧光团（供体）的激发态与封闭形式之间的定量共振能量转移观察到了光致变色单元1-3（受体）
• Digital Photoswitching of Fluorescence Based on the Photochromism of Diarylethene Derivatives at a Single-Molecule Level
  作者：Tuyoshi Fukaminato、Takatoshi Sasaki、Tsuyoshi Kawai、Naoto Tamai、Masahiro Irie

  DOI：10.1021/ja047169n

  日期：2004.11.1

  digital on/off switching between two discrete states was observed at the single-molecule level. The "on"- and "off"-times were dependent on the power of UV and visible light. When the power of UV and visible light was increased, the average on- and off-times became short in proportion to the reciprocal power of the light. The response-times were found to show distribution. The distribution of the on- and

  通过使用荧光技术在单分子水平上检测二芳基乙烯衍生物的光致变色反应。合成了荧光光开关分子，其中光致变色二芳基乙烯和荧光双（苯乙炔基）蒽单元通过金刚烷基间隔键连接，并在溶液中以及在单分子聚合物膜上跟踪紫外线和可见光照射后的荧光转换等级。尽管在溶液中荧光强度在紫外线和可见光照射下逐渐改变，但在单分子水平上观察到两个离散状态之间的数字开/关切换。“开”和“关”时间取决于紫外线和可见光的功率。当紫外线和可见光的功率增加时，平均开启和关闭时间与光的相互功率成比例地变短。发现响应时间显示分布。通断时间的分布被认为反映了微环境和分子构象的差异。
• New Photoswitching Unit for Magnetic Interaction:  Diarylethene with 2,5-Bis(arylethynyl)-3-thienyl Group
  作者：Naoki Tanifuji、Masahiro Irie、Kenji Matsuda

  DOI：10.1021/ja053200p

  日期：2005.9.28

  Photoswitching of the intramolecular magnetic interaction was demonstrated using diarylethenes with 2,5-bis(arylethynyl)-4-methyi-3-thienyl side group. Two nitroxide radicals were placed at each end of the 2,5-bis(arylethynyl)-4-methyl-3-thienyI group. Three kinds of aryl groups, 2,5-thienylene, p-phenylene, and m-phenylene groups, were used in the arylethynyl moiety. The diarylethene photoswitching units have an extended pi-conjugated chain on one side of the diarylethene. The photochromic reactivity was dependent on the arylethynyl group. Diarylethenes with m-phenylene group showed an efficient photochromic reactivity. Along with the photochromic reaction the diarylethenes showed photoswitching of an ESR spectrum originating from the change in the magnetic interaction between two unpaired electrons. The open-ring isomer showed stronger exchange interaction than the photogenerated closed-ring isomer. The magnetic interaction between two radicals via the pi-conjugated chain was altered by photocyclization due to the change of the hybrid orbital at the 2-position of the thiophene ring from sp(2) to sp(3).
• Conformational Control of Photochromic Reactivity in a Diarylethene Single Crystal
  作者：Seiya Kobatake、Yoshimichi Matsumoto、Masahiro Irie

  DOI：10.1002/anie.200462426

  日期：2005.3.29
• Synthesis of New Photochromic Diarylethenes Having 2,5-Bis(trimethylsilylethynyl)-3-Thienyl Unit
  作者：Naoki Tanifuji、Kenji Matsuda、Masahiro Irie

  DOI：10.1080/15421400590946190

  日期：2005.5.1

  New diarylethenes having a trimethylsilylethynyl substituent at the 2,5-position of the thiophene ring were synthesized. Diarylethene moiety are located in the middle of the pi-conjugated chain. These molecules underwent a photochromic reaction in solution. This molecule can be used as a switching unit in the it-conjugated polymer or oligomer.