2-acetylamino-N-[2-(4-hydroxyphenyl)ethyl]acrylamide | 646071-98-9

• 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]acrylamide
• 英文别名: 2-Propenamide, 2-(acetylamino)-N-[2-(4-hydroxyphenyl)ethyl]-；2-acetamido-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
• CAS: 646071-98-9
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: USEGPMXTEKYCHH-UHFFFAOYSA-N

物化性质

• 沸点：
  610.4±55.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetylamino-N-[2-(4-hydroxyphenyl)ethyl]acrylamide 在 ammonium hydroxide 作用下， 反应 168.0h， 以98%的产率得到2-乙酰氨基-3-氨基-N-[2-(4-羟基苯基)乙基]丙酰胺
  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
• 作为产物：
  描述：

  对羟基苯乙胺 、 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 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以60%的产率得到2-acetylamino-N-[2-(4-hydroxyphenyl)ethyl]acrylamide
  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。
• Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids
  作者：Hanna M. Key、Scott J. Miller

  DOI：10.1021/jacs.7b08775

  日期：2017.11.1

  potassium salts as applied in the case of thiostrepton leads to a nearly full reversal of the enantioselectivity of the reaction. As such, this study of site-selective catalysis in a complex molecular setting also delivered synergistic insights in the arena of enantioselective catalysis. In addition, these studies greatly expand the number of known thiostrepton analogues obtained by any method and reveal a

  通过复杂分子的催化剂控制、选择性功能化来合成复杂的生物活性分子是一种新兴的能力。我们描述了 Rh 催化的共轭芳基化在硫链丝菌素修饰中的应用，硫链丝菌素是一种复杂的分子，具有强效抗菌特性，已知的类似物很少。通过这种方法，我们实现了硫链丝菌肽中存在的一个亚末端脱氢丙氨酸残基 (Dha16) 的位点和立体选择性功能化。这种方法的广泛范围使得能够制备和分离 24 种新的硫链丝菌素类似物，其生物学测试表明，硫链丝菌素的抗菌活性可以耐受 Dha16 到一系列氨基酸的改变。对该 Rh 催化过程的进一步分析表明，钠盐或钾盐的使用对于实现高立体选择性至关重要。通过应用于从脱氢丙氨酸单体合成氨基酯和酰胺，进一步研究了催化剂体系，发现该过程在比先前报道的类似反应更温和的条件下以高达 93:7 的 er 发生。此外，在硫链丝菌肽的情况下添加相同的钠盐和钾盐导致反应的对映选择性几乎完全逆转。因此，这项复杂分子环境中
• 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.