2-(N-methyl)benzylamino-3-methoxycarbonyl-5-phenylthiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-(N-methyl)benzylamino-3-methoxycarbonyl-5-phenylthiophene
• 英文别名: Methyl 2-[benzyl(methyl)amino]-5-phenylthiophene-3-carboxylate；methyl 2-[benzyl(methyl)amino]-5-phenylthiophene-3-carboxylate
• 化学式: C₂₀H₁₉NO₂S
• 分子量: 337.442
• InChiKey: AYFWTLHLWFALRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙炔酸甲酯 、 2-(N-methyl)benzylamino-3-(4-nitrophenyl)-5-phenyl-1,3-thiazolium-4-olate 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到6-(N-methyl)benzylamino-5-methoxycarbonyl-1-(4-nitrophenyl)-3-phenylpyridin-2-one
  参考文献：
  名称：

  [3+2]-Cycloadditions of 2-Aminothioisomünchnones to Alkynes: Synthetic Scope and Mechanistic Insights

  摘要：

  This manuscript describes the regiospecific 1,3-dipolar cycloadditions of 2-aminothioisomunchnones (1-3) with methyl propiolate. The structure of compound 4 has been unequivocally determined by X-ray crystallography. Based on these experimental arguments and a theoretical rationale that supports the regiochemistry observed, a mechanistic pathway is discussed to account for the formation of pyridone or thiophene derivatives. The protocol has also been extended to the cycloadditions of aminothioisomunchnones derived from carbohydrates with dimethyl acetylenedicarboxylate to afford interesting glycosylaminoheterocycles. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00022-3

文献信息

• [3+2]-Cycloadditions of 2-Aminothioisomünchnones to Alkynes: Synthetic Scope and Mechanistic Insights
  作者：Marı́a J Arévalo、Martı́n Avalos、Reyes Babiano、Pedro Cintas、Michael B Hursthouse、José L Jiménez、Mark E Light、Ignacio López、Juan C Palacios

  DOI：10.1016/s0040-4020(00)00022-3

  日期：2000.2

  This manuscript describes the regiospecific 1,3-dipolar cycloadditions of 2-aminothioisomunchnones (1-3) with methyl propiolate. The structure of compound 4 has been unequivocally determined by X-ray crystallography. Based on these experimental arguments and a theoretical rationale that supports the regiochemistry observed, a mechanistic pathway is discussed to account for the formation of pyridone or thiophene derivatives. The protocol has also been extended to the cycloadditions of aminothioisomunchnones derived from carbohydrates with dimethyl acetylenedicarboxylate to afford interesting glycosylaminoheterocycles. (C) 2000 Elsevier Science Ltd. All rights reserved.