3-bromo-2,5-diiodo-4-methylthiophene | 617689-00-6

• 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: 3-bromo-2,5-diiodo-4-methylthiophene
• CAS: 617689-00-6
• 化学式: C₅H₃BrI₂S
• 分子量: 428.858
• InChiKey: QLIMKFSPYQTAOV-UHFFFAOYSA-N

物化性质

• 熔点：
  79.5 °C
• 沸点：
  337.5±42.0 °C(Predicted)
• 密度：
  2.757±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  3-bromo-2,5-diiodo-4-methylthiophene 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 正丁基锂 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 10.5h， 生成 1-[2,5-bis(5-formyl-2-thienylethynyl)-4-methyl-3-thienyl]-2-[2,4-dimethyl-5-phenyl-3-thienyl]hexafluorocyclopentene
  参考文献：
  名称：

  New Photoswitching Unit for Magnetic Interaction:  Diarylethene with 2,5-Bis(arylethynyl)-3-thienyl Group

  摘要：

  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).

  DOI：

  10.1021/ja053200p
• 作为产物：
  描述：

  3-溴-4-甲基噻吩 在 溶剂黄146 硫酸 、 碘 、 高碘酸 作用下， 反应 3.0h， 以92%的产率得到3-bromo-2,5-diiodo-4-methylthiophene
  参考文献：
  名称：

  New Photoswitching Unit for Magnetic Interaction:  Diarylethene with 2,5-Bis(arylethynyl)-3-thienyl Group

  摘要：

  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).

  DOI：

  10.1021/ja053200p

文献信息

• Phenyl substituted thiophenes as estrogenic agents
  申请人：——

  公开号：US20030199570A1

  公开（公告）日：2003-10-23

  This invention provides estrogen receptor modulators of formula I, having the structure 1 wherein, R 1 , R 2 , R 3 , X, and Y are as defined in the specification, or a pharmaceutically acceptable salt thereof.

  该发明提供了式I的雌激素受体调节剂，其具有以下结构：1 其中，R1、R2、R3、X和Y如规范中所定义，或其药学上可接受的盐。
• 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.