2-甲基-3-羟甲基苯并噻吩 | 55085-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2-甲基-3-羟甲基苯并噻吩
• 英文名称: 2-Methyl-3-hydroxymethylbenzothiophene
• 英文别名: (2-methyl-benzo[b]thiophen-3-yl)-methanol；(2-Methyl-1-benzothiophen-3-yl)methanol；(2-methyl-1-benzothiophen-3-yl)methanol
• CAS: 55085-93-3
• 化学式: C₁₀H₁₀OS
• 分子量: 178.255
• InChiKey: FAOIGRKLBGVLDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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

• 作为产物：
  描述：

  3-氯甲基-2-甲基苯并噻吩 生成 2-甲基-3-羟甲基苯并噻吩
  参考文献：
  名称：

  Transformations of six isomers of dimethylbenzothiophene by three Pseudomonas strains

  摘要：

  Dimethylbenzothiophenes are among the sulfur heterocycles in petroleum that are known to be degraded by microbial activity. Six of the 15 possible isomers of dimethylbenzothiophene were synthesized and used in biotransformation studies with three Pseudomonas isolates that oxidize a variety of condensed thiophenes including methylbenzothiophenes and methyldibenzothiophenes. The isomers of dimethylbenzothiophene were chosen to have a variety of substitution patterns: both methyl groups on the thiophene ring (the 2,3-isomer); a methyl group on each of the rings (the 2,7-, 3,5- and 3,7-isomers); and both methyl groups on the benzene ring (the 4,6- and 4,7-isomers). Each isolate was grown on l-methylnaphthalene or glucose in the presence of one of the dimethylbenzothiophenes and culture extracts were analyzed to identify nearly 30 sulfur-containing metabolites in total. Sulfoxides and sulfones were commonly found metabolites in culture extracts from the 2,3-, 2,7- and 3,7-isomers, whereas 2,3-diones, 3(2H)-ones and 2(3H)-ones were formed from the 4,6- and 4,7-isomers. High-molecular-weight products, some of which were tentatively identified as tetramethylbenzo[b]naphtho[1,2-d]thiophen were detected in the extracts of cultures incubated with 4,6- or 4,7-dimethylbenzothiophene. The methyl groups of all of the isomers, except 4,6-, were oxidized to give hydroxymethyl-methylbenzothiophenes and methylbenzothiophene-carboxylic acids, and these were the only products detected from the oxidation of 3,5-dimethylbenzothiophene.

  DOI：

  10.1007/bf00058180

文献信息

• Abnormal Reactions of 2-Thianaphthenylmethylmagnesium Chloride
  作者：Russell Gaertner

  DOI：10.1021/ja01123a054

  日期：1952.2
• Transformations of six isomers of dimethylbenzothiophene by three Pseudomonas strains
  作者：Kevin G. Kropp、Sanja Saftić、Jan T. Andersson、Phillip M. Fedorak

  DOI：10.1007/bf00058180

  日期：1996.6

  Dimethylbenzothiophenes are among the sulfur heterocycles in petroleum that are known to be degraded by microbial activity. Six of the 15 possible isomers of dimethylbenzothiophene were synthesized and used in biotransformation studies with three Pseudomonas isolates that oxidize a variety of condensed thiophenes including methylbenzothiophenes and methyldibenzothiophenes. The isomers of dimethylbenzothiophene were chosen to have a variety of substitution patterns: both methyl groups on the thiophene ring (the 2,3-isomer); a methyl group on each of the rings (the 2,7-, 3,5- and 3,7-isomers); and both methyl groups on the benzene ring (the 4,6- and 4,7-isomers). Each isolate was grown on l-methylnaphthalene or glucose in the presence of one of the dimethylbenzothiophenes and culture extracts were analyzed to identify nearly 30 sulfur-containing metabolites in total. Sulfoxides and sulfones were commonly found metabolites in culture extracts from the 2,3-, 2,7- and 3,7-isomers, whereas 2,3-diones, 3(2H)-ones and 2(3H)-ones were formed from the 4,6- and 4,7-isomers. High-molecular-weight products, some of which were tentatively identified as tetramethylbenzo[b]naphtho[1,2-d]thiophen were detected in the extracts of cultures incubated with 4,6- or 4,7-dimethylbenzothiophene. The methyl groups of all of the isomers, except 4,6-, were oxidized to give hydroxymethyl-methylbenzothiophenes and methylbenzothiophene-carboxylic acids, and these were the only products detected from the oxidation of 3,5-dimethylbenzothiophene.