3-hydroxy-2-methylene-3-(thiazol-2-yl)propionamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-hydroxy-2-methylene-3-(thiazol-2-yl)propionamide
• 英文别名: 2-[Hydroxy(1,3-thiazol-2-yl)methyl]prop-2-enamide
• 化学式: C₇H₈N₂O₂S
• 分子量: 184.219
• InChiKey: BDSLCJHEERHCGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-醛基噻唑 、 丙烯酰胺 在 三乙烯二胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以99%的产率得到3-hydroxy-2-methylene-3-(thiazol-2-yl)propionamide
  参考文献：
  名称：

  Successful Baylis−Hillman Reaction of Acrylamide with Aromatic Aldehydes

  摘要：

  Acrylamide and aromatic aldehydes were found to undergo the Baylis-Hillman reaction at ambient temperature in an aqueous medium in the presence of a stoichiometric amount of base catalyst, DABCO, to give the corresponding 3-hydroxy-2-methylenepropionamides in 61-99% yield. A faster competing, but reverible, non-Baylis-Hillman reaction was initially observed under the conditions to form N-acylhemiaminals, which later disappeared, as the desired Baylis-Hillman adduct was formed as the major product over an extended period of time (12-48 h). This represents the first demonstration of the Baylis-Hillman reaction of aldehydes with acrylamides, which were thought to be inert under atmospheric pressure and at ambient temperature.

  DOI：

  10.1021/jo016004j

文献信息

• Successful Baylis−Hillman Reaction of Acrylamide with Aromatic Aldehydes
  作者：Chengzhi Yu、Longqin Hu

  DOI：10.1021/jo016004j

  日期：2002.1.1

  Acrylamide and aromatic aldehydes were found to undergo the Baylis-Hillman reaction at ambient temperature in an aqueous medium in the presence of a stoichiometric amount of base catalyst, DABCO, to give the corresponding 3-hydroxy-2-methylenepropionamides in 61-99% yield. A faster competing, but reverible, non-Baylis-Hillman reaction was initially observed under the conditions to form N-acylhemiaminals, which later disappeared, as the desired Baylis-Hillman adduct was formed as the major product over an extended period of time (12-48 h). This represents the first demonstration of the Baylis-Hillman reaction of aldehydes with acrylamides, which were thought to be inert under atmospheric pressure and at ambient temperature.