2-acetylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-(isopropylsulfanyl)propionamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-acetylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-(isopropylsulfanyl)propionamide
• 英文别名: 2-acetamido-N-[2-(4-hydroxyphenyl)ethyl]-3-propan-2-ylsulfanylpropanamide
• 化学式: C₁₆H₂₄N₂O₃S
• 分子量: 324.444
• InChiKey: GILCKQPTPAAEIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙酰氨基丙烯酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-acetylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-(isopropylsulfanyl)propionamide
  参考文献：
  名称：

  Michael Addition of Amines and Thiols to Dehydroalanine Amides:  A Remarkable Rate Acceleration in Water

  摘要：

  In water, the rate of Michael addition of amines and thiols to dehydroalanine amides was greatly accelerated, leading to shorter reaction times and higher yields. The scope of the new conditions was tested with a range of amines, thiols, and dehydroalanine amides. The ease and efficiency of this method provides an attractive route to the synthesis of natural and unnatural amino acid derivatives.

  DOI：

  10.1021/jo034762z

文献信息

• Organic reactions in frozen water: Michael addition of amines and thiols to the dehydroalanine side chain of nocathiacins
  作者：B.Narasimhulu Naidu、Wenying Li、Margaret E. Sorenson、Timothy P. Connolly、John A. Wichtowski、Yunhui Zhang、Oak K. Kim、John D. Matiskella、Kin S. Lam、Joanne J. Bronson、Yasutsugu Ueda

  DOI：10.1016/j.tetlet.2003.11.081

  日期：2004.1

  In order to overcome this problem, we developed unique conditions in which Michael addition of amine and thiol nucleophiles to the dehydroalanine moiety of nocathiacins was successfully achieved in frozen water. Under these conditions, the Michael addition was highly chemoselective, very efficient and provided good isolated yields of the desired products.

  Nocathiacins是密集功能化的环状噻唑基肽天然产物，对多种革兰氏阳性细菌（包括多种多重耐药菌株）具有强大的体外和体内抗菌活性。尝试在已知条件下制备迈克尔加合物导致形成复杂的产物混合物。为了克服这个问题，我们开发了独特的条件，其中在冷冻水中成功地实现了将胺和巯基亲核试剂的迈克尔加成到Nocathiacins的脱氢丙氨酸部分中。在这些条件下，迈克尔加成物具有高度的化学选择性，非常有效，并提供了所需产物的良好分离产率。
• Michael Addition of Amines and Thiols to Dehydroalanine Amides:  A Remarkable Rate Acceleration in Water
  作者：B. Narasimhulu Naidu、Margaret E. Sorenson、Timothy P. Connolly、Yasutsugu Ueda

  DOI：10.1021/jo034762z

  日期：2003.12.1

  In water, the rate of Michael addition of amines and thiols to dehydroalanine amides was greatly accelerated, leading to shorter reaction times and higher yields. The scope of the new conditions was tested with a range of amines, thiols, and dehydroalanine amides. The ease and efficiency of this method provides an attractive route to the synthesis of natural and unnatural amino acid derivatives.