3-methylbenzothiophene-7-methanol | 130220-06-3

• 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: 3-methylbenzothiophene-7-methanol
• 英文别名: (3-Methyl-1-benzothiophen-7-yl)methanol
• CAS: 130220-06-3
• 化学式: C₁₀H₁₀OS
• 分子量: 178.255
• InChiKey: UAULWITUJLWDGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  338.5±27.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  3-methylbenzothiophene-7-methanol 在 溴 、 1,2-双(二苯基膦)乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 7-(bromomethyl)-3-methylbenzothiophene
  参考文献：
  名称：

  Synthesis and structure-activity relationships of benzo[b]thienylallylamine antimycotics

  摘要：

  Benzo[b]thiophene analouges of the allylamine antimycotic terbinafine (2) bearing the side chain at various positions and optionally substituted by halogen have been prepared and their antifungal activity studied. Derivatives bearing the side chain at positions 3, 4, or 7 are bioequivalents of 2. Compounds containing the allylamine side chain at position 7, with a further substituent at position 3, showed significantly enhanced activity against Candida albicans, an effect which appears to be specifically linked only to this particular substitution pattern. 3-Chloro-7-benzo[b]thienyl derivative 7m was found to be the most potent allylamine antimycotic identified so far. In general, substituted benzo[b]thiophenes can be used not only as potential equivalents of naphthalene in bioactive compounds but also as a tool to selectively modify biological activities.

  DOI：

  10.1021/jm00105a011
• 作为产物：
  描述：

  methyl 3-methyl-7-benzothiophenecarboxylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以97%的产率得到3-methylbenzothiophene-7-methanol
  参考文献：
  名称：

  Synthesis and structure-activity relationships of benzo[b]thienylallylamine antimycotics

  摘要：

  Benzo[b]thiophene analouges of the allylamine antimycotic terbinafine (2) bearing the side chain at various positions and optionally substituted by halogen have been prepared and their antifungal activity studied. Derivatives bearing the side chain at positions 3, 4, or 7 are bioequivalents of 2. Compounds containing the allylamine side chain at position 7, with a further substituent at position 3, showed significantly enhanced activity against Candida albicans, an effect which appears to be specifically linked only to this particular substitution pattern. 3-Chloro-7-benzo[b]thienyl derivative 7m was found to be the most potent allylamine antimycotic identified so far. In general, substituted benzo[b]thiophenes can be used not only as potential equivalents of naphthalene in bioactive compounds but also as a tool to selectively modify biological activities.

  DOI：

  10.1021/jm00105a011

文献信息

• NUSSBAUMER, PETER;PETRANYI, GABOR;STUTZ, ANTON, J. MED. CHEM., 34,(1991) N, C. 65-73
  作者：NUSSBAUMER, PETER、PETRANYI, GABOR、STUTZ, ANTON

  DOI：——

  日期：——