2',3'-dihydro-8'-methyl-2-methylthio-2',4-dioxospiro[2-cyclopenten-1,3'-imidazo[1,2-a]pyridin]-3-carboxylic acid ethyl ester | 1256269-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2',3'-dihydro-8'-methyl-2-methylthio-2',4-dioxospiro[2-cyclopenten-1,3'-imidazo[1,2-a]pyridin]-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2',3'-dihydro-8'-methyl-2-methylthio-2',4-dioxospiro[cyclopent-2-ene-1,3'-imidazo[1,2-a]pyridine]-3-carboxylate
• CAS: 1256269-71-2
• 化学式: C₁₆H₁₆N₂O₄S
• 分子量: 332.38
• InChiKey: UJAJEHUBOHKSJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76.04
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2',3'-dihydro-8'-methyl-2-methylthio-2',4-dioxospiro[2-cyclopenten-1,3'-imidazo[1,2-a]pyridin]-3-carboxylic acid ethyl ester 、 甘氨酸乙酯盐酸盐 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以99%的产率得到2',3'-dihydro-2-(ethoxycarbonylmethyl)amino-8'-methyl-2',4-dioxospiro[2-cyclopenten-1,3'-imidazo[1,2-a]pyridin]-3-carboxylic acid ethyl ester
  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 、 (bis(methylthio))methylidene-8-methylimidazo[1,2-a]pyridin-2(3H)-one 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 11.0h， 以90%的产率得到2',3'-dihydro-8'-methyl-2-methylthio-2',4-dioxospiro[2-cyclopenten-1,3'-imidazo[1,2-a]pyridin]-3-carboxylic acid ethyl ester
  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