ethyl 2',3'-dihydro-2-methylthio-2',4-dioxospiro[cyclopent-2-ene-1,3'-imidazo[1,2-a]pyridine]-3-carboxylate | 1256269-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: ethyl 2',3'-dihydro-2-methylthio-2',4-dioxospiro[cyclopent-2-ene-1,3'-imidazo[1,2-a]pyridine]-3-carboxylate
• 英文别名: Ethyl 2-methylsulfanyl-2',5-dioxospiro[cyclopentene-3,3'-imidazo[1,2-a]pyridine]-1-carboxylate
• CAS: 1256269-70-1
• 化学式: C₁₅H₁₄N₂O₄S
• 分子量: 318.353
• InChiKey: HQMCCTZXLAMOLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  哌啶 、 ethyl 2',3'-dihydro-2-methylthio-2',4-dioxospiro[cyclopent-2-ene-1,3'-imidazo[1,2-a]pyridine]-3-carboxylate 以 氯仿 为溶剂， 反应 7.0h， 以79%的产率得到ethyl 2',3'-dihydro-2',4-dioxo-2-piperidinospiro[cyclopent-2-ene-1,3'-imidazo[1,2-a]pyridine]-3-carboxylate
  参考文献：
  名称：

  Synthesis of Spiro[2-cyclopentene-1,3’-imidazo[1,2-a]pyridine] Derivatives and Their Interesting Behavior in 1H-NMR Spectra in Deuteriochloroform

  摘要：

  Ethyl 2',3'-dihydro-2-methylthio-2',4-dioxospiro[2-cyclopentene-1,3'-imidazo[1,2-a]pyridine]-3-carboxylates were synthesized from the reactions of 3-[bis(methylthio)methylene]-2(3H)-imidazo[1,2-a]pyridinones with ethyl 4-chloroacetoacetate in the presence of a base. The 2-methylthio group in these Spiro compounds was easily replaced with some primary and secondary amines to afford the corresponding 2-amino derivatives. Very interestingly, the proton signals of these Spiro compounds in the H-1-NMR spectra in deuteriochloroform (CDCl3) changed with an increase in the sample concentration, and the analysis for the magnitude and the direction of each proton shift disclosed the conformational change of the cyclopentenone moiety in this molecule.

  DOI：

  10.3987/com-10-11985
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 、 3-[bis(methylthio)methylene]-2(3H)-imidazo[1,2-a]pyridinone 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 以69%的产率得到ethyl 2',3'-dihydro-2-methylthio-2',4-dioxospiro[cyclopent-2-ene-1,3'-imidazo[1,2-a]pyridine]-3-carboxylate
  参考文献：
  名称：

  Synthesis of Spiro[2-cyclopentene-1,3’-imidazo[1,2-a]pyridine] Derivatives and Their Interesting Behavior in 1H-NMR Spectra in Deuteriochloroform

  摘要：

  Ethyl 2',3'-dihydro-2-methylthio-2',4-dioxospiro[2-cyclopentene-1,3'-imidazo[1,2-a]pyridine]-3-carboxylates were synthesized from the reactions of 3-[bis(methylthio)methylene]-2(3H)-imidazo[1,2-a]pyridinones with ethyl 4-chloroacetoacetate in the presence of a base. The 2-methylthio group in these Spiro compounds was easily replaced with some primary and secondary amines to afford the corresponding 2-amino derivatives. Very interestingly, the proton signals of these Spiro compounds in the H-1-NMR spectra in deuteriochloroform (CDCl3) changed with an increase in the sample concentration, and the analysis for the magnitude and the direction of each proton shift disclosed the conformational change of the cyclopentenone moiety in this molecule.

  DOI：

  10.3987/com-10-11985

文献信息

• BRAIN FUNCTION IMPROVER
  申请人：Tohoku University

  公开号：EP2808021A1

  公开（公告）日：2014-12-03

  The present invention provides a pharmaceutical composition used in improving brain function including a compound of formula (I).

  本发明提供了一种用于改善脑功能的药物组合物，其中包括式（I）化合物。
• BRAIN FUNCTION IMPROVING AGENT
  申请人：Tohoku University

  公开号：EP2808021B1

  公开（公告）日：2017-08-23
• US9173878B2
  申请人：——

  公开号：US9173878B2

  公开（公告）日：2015-11-03