(E)-3-(5-Methyl-benzo[b]thiophen-2-yl)-acrylic acid ethyl ester | 179728-94-0

• 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: (E)-3-(5-Methyl-benzo[b]thiophen-2-yl)-acrylic acid ethyl ester
• 英文别名: ethyl 3-(5-methyl-1-benzothiophen-2-yl)prop-2-enoate
• CAS: 179728-94-0
• 化学式: C₁₄H₁₄O₂S
• 分子量: 246.33
• InChiKey: FFVZNSKIXRDTEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(5-Methyl-benzo[b]thiophen-2-yl)-acrylic acid ethyl ester 在 镍 sodium hydroxide 、 氢气 、 苄基三甲基氢氧化铵 作用下， 以 乙醇 为溶剂， 25.0~80.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 4-Amino-3-(5-methyl-benzo[b]thiophen-2-yl)-butyric acid
  参考文献：
  名称：

  3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABAB ligands. Synthesis and structure-activity relationship studies

  摘要：

  Baclofen (beta-p-chlorophenyl GABA) is one of the selective agonists for the bicuculline-insensitive GABA(B) receptors. In the search for new compounds that bind to GABA(B) receptors it is very important to clarify the structural requirements. We report the syntheses of and binding studies on various S-heteroaromatic (benzo[b]furan and benzo[b]thiophen)aminobutyric acids. The 4-amino-3-(7-methyl-benzo[b]furan-2-yl)butanoic acid 8g is a potent and specific ligand for GABA(B) receptors, with an IC50 value of 5.4 mu M in the displacement of [H-3]GABA.

  DOI：

  10.1016/0223-5234(96)85165-8
• 作为产物：
  描述：

  5-甲基-1-苯并噻吩-2-甲醛 、 乙氧甲酰基亚甲基三苯基膦 以 苯 为溶剂， 反应 7.0h， 以58%的产率得到(E)-3-(5-Methyl-benzo[b]thiophen-2-yl)-acrylic acid ethyl ester
  参考文献：
  名称：

  3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABAB ligands. Synthesis and structure-activity relationship studies

  摘要：

  Baclofen (beta-p-chlorophenyl GABA) is one of the selective agonists for the bicuculline-insensitive GABA(B) receptors. In the search for new compounds that bind to GABA(B) receptors it is very important to clarify the structural requirements. We report the syntheses of and binding studies on various S-heteroaromatic (benzo[b]furan and benzo[b]thiophen)aminobutyric acids. The 4-amino-3-(7-methyl-benzo[b]furan-2-yl)butanoic acid 8g is a potent and specific ligand for GABA(B) receptors, with an IC50 value of 5.4 mu M in the displacement of [H-3]GABA.

  DOI：

  10.1016/0223-5234(96)85165-8

文献信息

• Benzo[c]carbazole derivatives produced by an effective Diels–Alder reaction: synthesis and structure–activity-relationship for surface coating
  作者：Xue-Qing Feng、Fei Zhang、Xiao-Peng He、Guo-Rong Chen、Xin-Yan Wu、Feng Sha

  DOI：10.1039/c6ra18398k

  日期：——

  We show the construction of a library of heteroatom-fused benzo[c]carbazole derivatives by a Diels–Alder reaction as effective surface-coating materials against copper corrosion in an acidic medium.

  我们展示了通过Diels-Alder反应构建杂原子稠合的苯并[ c ]咔唑衍生物库的方法，该库可有效抵抗酸性介质中的铜腐蚀。