ethyl 5-carbamoylthiophene-2-carboxylate | 1239315-91-3

• 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: ethyl 5-carbamoylthiophene-2-carboxylate
• CAS: 1239315-91-3
• 化学式: C₈H₉NO₃S
• mdl: MFCD19982270
• 分子量: 199.23
• InChiKey: LMHAUNCZNUZVMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴噻吩-2-甲酸乙酯 、 三氯乙酰异氰酸酯 在 lithium chloro-isopropyl-magnesium chloride 、 zinc(II) chloride 、 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以61%的产率得到ethyl 5-carbamoylthiophene-2-carboxylate
  参考文献：
  名称：

  Preparation of Primary Amides from Functionalized Organozinc Halides

  摘要：

  Organozinc halides, which are prepared either by direct zinc insertion or halogen magnesium exchange and subsequent transmetalation with ZnCl2, react smoothly with commercially available trichloroacetyl isocyanate to give, after hydrolysis, the corresponding primary amides. This method is compatible with a variety of functional groups such as an ester or a cyano group. Also heterocyclic-, alkenyl, and acetylenic zinc reagents are converted to the corresponding primary amides under these conditions.

  DOI：

  10.1021/ol101469f

文献信息

• Preparation of Primary Amides from Functionalized Organozinc Halides
  作者：Matthias A. Schade、Georg Manolikakes、Paul Knochel

  DOI：10.1021/ol101469f

  日期：2010.8.20

  Organozinc halides, which are prepared either by direct zinc insertion or halogen magnesium exchange and subsequent transmetalation with ZnCl2, react smoothly with commercially available trichloroacetyl isocyanate to give, after hydrolysis, the corresponding primary amides. This method is compatible with a variety of functional groups such as an ester or a cyano group. Also heterocyclic-, alkenyl, and acetylenic zinc reagents are converted to the corresponding primary amides under these conditions.