乙基8'-甲基-2'，4-二氧-2-(哌啶-1-基)-2'H-螺[环戊[2]烯-1,3'-咪唑并[1,2-a]吡啶]-3-羧酸盐 | 1256269-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 乙基8'-甲基-2'，4-二氧-2-(哌啶-1-基)-2'H-螺[环戊[2]烯-1,3'-咪唑并[1,2-a]吡啶]-3-羧酸盐
• 英文名称: ethyl 8-methyl-2,4-dioxo-2-(piperidin-1-yl)-2H-spiro[cyclopentane-1,3-imidazo[1,2-a]pyridin]-2-ene-3-carboxylate
• 英文别名: SAK3；Ethyl 8'-methyl-2',4-dioxo-2-(piperidin-1-yl)-2'H-spiro[cyclopent[2]ene-1,3'-imidazo[1,2-a]pyridine]-3-carboxylate；ethyl 8'-methyl-2',5-dioxo-2-piperidin-1-ylspiro[cyclopentene-3,3'-imidazo[1,2-a]pyridine]-1-carboxylate
• CAS: 1256269-87-0
• 化学式: C₂₀H₂₃N₃O₄
• 分子量: 369.42
• InChiKey: WZHBYTVHUFURPY-UHFFFAOYSA-N

物化性质

• 沸点：
  539.3±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (bis(methylthio))methylidene-8-methylimidazo[1,2-a]pyridin-2(3H)-one 在 potassium tert-butylate 作用下， 以 氯仿 、 叔丁醇 为溶剂， 反应 17.0h， 生成 乙基8'-甲基-2'，4-二氧-2-(哌啶-1-基)-2'H-螺[环戊[2]烯-1,3'-咪唑并[1,2-a]吡啶]-3-羧酸盐
  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 IMPROVING AGENT
  申请人：Tohoku University

  公开号：US20150045385A1

  公开（公告）日：2015-02-12

  The present invention provides a pharmaceutical composition used in improving brain function including a compound of formula (I).
• US9173878B2
  申请人：——

  公开号：US9173878B2

  公开（公告）日：2015-11-03
• Synthesis of Spiro[2-cyclopentene-1,3’-imidazo[1,2-a]pyridine] Derivatives and Their Interesting Behavior in 1H-NMR Spectra in Deuteriochloroform
  作者：Akikazu Kakehi、Takashi Abe、Hiroyuki Suga、Yukihisa Okumura、Kennosuke Itoh

  DOI：10.3987/com-10-11985

  日期：——

  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.