6-hydroxy-2,3,4,7-tetramethylbenzo[b]thiophene | 569653-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 6-hydroxy-2,3,4,7-tetramethylbenzo[b]thiophene
• 英文别名: 2,3,4,7-Tetramethyl-1-benzothiophen-6-ol
• CAS: 569653-21-0
• 化学式: C₁₂H₁₄OS
• 分子量: 206.309
• InChiKey: YEWITTKSUIJQOS-UHFFFAOYSA-N

物化性质

• 熔点：
  136-138 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  362.8±37.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-双(4-甲氧基苯基)-2-丙炔-1-醇 、 6-hydroxy-2,3,4,7-tetramethylbenzo[b]thiophene 在 aluminum oxide 作用下， 以 甲苯 为溶剂， 反应 0.67h， 以20%的产率得到2,3,4,9-tetramethyl-7,7-bis(4-methoxyphenyl)-[7H]-chromene[7,6-b]thiophene
  参考文献：
  名称：

  Synthesis and photochromic behaviour of new methyl induced linear and angular thieno-2H-chromenes

  摘要：

  New methyl induced linear and angular thieno-2H-chromenes 4, 5 and 6 were prepared by reaction of new methylated 6-hydroxybenzo[b]thiophenes 2 (a, b and c) and propargylic alcohols 3a and 3b, using acidic Alumina Brockmann I as catalyst and drying agent. Compounds 2 were prepared in good to excellent yields in a 'one pot' three step reaction from the corresponding bromo compounds 1. The photochromic behaviour of compounds 4, 5 and 6b was evaluated with the aid of a classical set of spectrokinetic parameters, and compared to reference compounds that are benzoannellated in the 5,6 and 6,7 positions of the chromene (naphthopyrans) and also to thieno-2H-chromenes 7 and 8, previously prepared, which are analogues of 5a. The resistance to fatigue (photodegradation) under continuous irradiation was also evaluated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00262-x
• 作为产物：
  描述：

  6-bromo-2,3,4,7-tetramethylbenzo[b]thiophene 在 正丁基锂 、 硼酸三丁酯 、 双氧水 、 溶剂黄146 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 4.33h， 以73%的产率得到6-hydroxy-2,3,4,7-tetramethylbenzo[b]thiophene
  参考文献：
  名称：

  Synthesis and photochromic behaviour of new methyl induced linear and angular thieno-2H-chromenes

  摘要：

  New methyl induced linear and angular thieno-2H-chromenes 4, 5 and 6 were prepared by reaction of new methylated 6-hydroxybenzo[b]thiophenes 2 (a, b and c) and propargylic alcohols 3a and 3b, using acidic Alumina Brockmann I as catalyst and drying agent. Compounds 2 were prepared in good to excellent yields in a 'one pot' three step reaction from the corresponding bromo compounds 1. The photochromic behaviour of compounds 4, 5 and 6b was evaluated with the aid of a classical set of spectrokinetic parameters, and compared to reference compounds that are benzoannellated in the 5,6 and 6,7 positions of the chromene (naphthopyrans) and also to thieno-2H-chromenes 7 and 8, previously prepared, which are analogues of 5a. The resistance to fatigue (photodegradation) under continuous irradiation was also evaluated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00262-x