5-formyl-4,4-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine | 1254344-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 5-formyl-4,4-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
• 英文别名: 4,4-Dimethyl-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carbaldehyde；4,4-dimethyl-6,7-dihydrothieno[3,2-c]pyridine-5-carbaldehyde
• CAS: 1254344-55-2
• 化学式: C₁₀H₁₃NOS
• 分子量: 195.285
• InChiKey: QIDUTWKAIOUAIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-formyl-4,4-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以67%的产率得到4,4-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
  参考文献：
  名称：

  An Efficient and Convenient Synthesis of 4,5,6,7-Tetrahydrothieno[3,2-c]pyridines by a Modified Pictet-Spengler Reaction via a Formyliminium Ion Intermediate

  摘要：

  A synthesis of N-formyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridines (5) was achieved in a highly efficient manner via trifluoroacetic acid catalyzed cyclization of formyliminium ion (4), which was produced by imination of 2-(2-thienyl)ethylamine (1) and a carbonyl compound (2) using titanium(IV) tetraisopropoxide followed by formylation with acetic-formic anhydride in a one-pot procedure. This modified Pictet-Spengler reaction provides a convenient method for preparing 4,5,6,7-tetahydrothieno[3,2-c]pyridines (6) possessing various substituents at C-4.

  DOI：

  10.3987/com-10-11992
• 作为产物：
  描述：

  噻吩乙胺 在 titanium(IV) isopropylate 、 乙酸酐 作用下， 反应 6.0h， 生成 5-formyl-4,4-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
  参考文献：
  名称：

  An Efficient and Convenient Synthesis of 4,5,6,7-Tetrahydrothieno[3,2-c]pyridines by a Modified Pictet-Spengler Reaction via a Formyliminium Ion Intermediate

  摘要：

  A synthesis of N-formyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridines (5) was achieved in a highly efficient manner via trifluoroacetic acid catalyzed cyclization of formyliminium ion (4), which was produced by imination of 2-(2-thienyl)ethylamine (1) and a carbonyl compound (2) using titanium(IV) tetraisopropoxide followed by formylation with acetic-formic anhydride in a one-pot procedure. This modified Pictet-Spengler reaction provides a convenient method for preparing 4,5,6,7-tetahydrothieno[3,2-c]pyridines (6) possessing various substituents at C-4.

  DOI：

  10.3987/com-10-11992

文献信息

• An Efficient and Convenient Synthesis of 4,5,6,7-Tetrahydrothieno[3,2-c]pyridines by a Modified Pictet-Spengler Reaction via a Formyliminium Ion Intermediate
  作者：Yoshie Horiguchi、Michikazu Kitabatake、Aki Hashimoto、Toshiaki Saitoh、Takehiro Sano、Kunihiko Mohri

  DOI：10.3987/com-10-11992

  日期：——

  A synthesis of N-formyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridines (5) was achieved in a highly efficient manner via trifluoroacetic acid catalyzed cyclization of formyliminium ion (4), which was produced by imination of 2-(2-thienyl)ethylamine (1) and a carbonyl compound (2) using titanium(IV) tetraisopropoxide followed by formylation with acetic-formic anhydride in a one-pot procedure. This modified Pictet-Spengler reaction provides a convenient method for preparing 4,5,6,7-tetahydrothieno[3,2-c]pyridines (6) possessing various substituents at C-4.