3-(Benzo[d]thiophen-3-yl)acrylic acid methyl ester | 477250-16-1

• 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-(Benzo[d]thiophen-3-yl)acrylic acid methyl ester
• 英文别名: methyl 3-(1-benzothiophen-3-yl)prop-2-enoate
• CAS: 477250-16-1
• 化学式: C₁₂H₁₀O₂S
• 分子量: 218.276
• InChiKey: SBHBQZMEVPCHFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  361.5±17.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(Benzo[d]thiophen-3-yl)acrylic acid methyl ester 在 5% Pd/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以96%的产率得到methyl 3-(benzothiophen-3-yl)propanoate
  参考文献：
  名称：

  A Palladium-Catalyzed Approach to Polycyclic Sulfur Heterocycles

  摘要：

  The synthesis of a variety of polycyclic thiophenes and benzothiophenes is accomplished via a palladium-catalyzed domino ortho-alkylation/direct arylation reaction. An examination of the intramolecular direct arylation of thiophenes suggests that an electrophilic metalation mechanism may be present. This method was further extended to include the synthesis of a (thieno)benzoxepine.

  DOI：

  10.1021/jo8020105
• 作为产物：
  描述：

  3-甲醛苯并噻吩 、 甲氧羰基亚甲基三苯基正膦 以 二氯甲烷 为溶剂， 以82%的产率得到3-(Benzo[d]thiophen-3-yl)acrylic acid methyl ester
  参考文献：
  名称：

  A Palladium-Catalyzed Approach to Polycyclic Sulfur Heterocycles

  摘要：

  The synthesis of a variety of polycyclic thiophenes and benzothiophenes is accomplished via a palladium-catalyzed domino ortho-alkylation/direct arylation reaction. An examination of the intramolecular direct arylation of thiophenes suggests that an electrophilic metalation mechanism may be present. This method was further extended to include the synthesis of a (thieno)benzoxepine.

  DOI：

  10.1021/jo8020105

文献信息

• Heterocyclic anti-epileptogenic agents and methods of use thereof
  申请人：Weaver F. Donald

  公开号：US20060014752A1

  公开（公告）日：2006-01-19

  Methods and compounds, such as β-heterocyclic-β-amino acids, useful for the inhibition of epileptogenesis are disclosed. Methods for preparing and using the β-heterocyclic-β-amino acids of the invention are also described.

  本发明公开了一种用于抑制癫痫发生的方法和化合物，例如β-杂环-β-氨基酸。还描述了制备和使用本发明中的β-杂环-β-氨基酸的方法。
• A Palladium-Catalyzed Approach to Polycyclic Sulfur Heterocycles
  作者：Andrew Martins、Mark Lautens

  DOI：10.1021/jo8020105

  日期：2008.11.21

  The synthesis of a variety of polycyclic thiophenes and benzothiophenes is accomplished via a palladium-catalyzed domino ortho-alkylation/direct arylation reaction. An examination of the intramolecular direct arylation of thiophenes suggests that an electrophilic metalation mechanism may be present. This method was further extended to include the synthesis of a (thieno)benzoxepine.