(Z)-N-benzyl-3-(benzylamino)but-2-enamide | 738-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-N-benzyl-3-(benzylamino)but-2-enamide
• 英文别名: (2Z)-N-benzyl-3-(benzylamino)but-2-enamide
• CAS: 738-79-4
• 化学式: C₁₈H₂₀N₂O
• 分子量: 280.37
• InChiKey: PIBHBBWFZYOPDH-QINSGFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-N-benzyl-3-(benzylamino)but-2-enamide 在 氯甲酸乙酯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 28.0h， 生成 5-Acetylamino-1-benzyl-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid benzylamide
  参考文献：
  名称：

  Formation of Dihydropyridone- and Pyridone-Based Peptide Analogs through Aza-Annulation of β-Enamino Ester and Amide Substrates with α-Amido Acrylate Derivatives

  摘要：

  The aza-annulation of beta-enamino ester and amide substrates with the mixed anhydride of 2-acetamidoacrylic acid was used for the efficient construction of highly substituted alpha-acetamido delta-lactam products. With the alpha-acetamido substituent, lactam functionality, and gamma-carboxylate group, these delta-lactam products represent an interesting class of conformationally restricted dipeptide analogs. The framework of this lactam hub is structurally related to that of an alpha-amino acid coupled with a beta-amino acid. When alpha-amino esters derived from naturally occurring amino acids were used in the enamine formation step, subsequent aza-annulation led to branched peptide surrogates with two C-termini that extended from a common N-terminus. Oxidation of the aza-annulation products resulted in the generation of a planar system with peptide functionality radiating from the 1, 3, and 5 positions of the pyridone hub. Alternatively, pyridone products could be formed directly from the enamino amides by reaction with 2-phenyl-4-(ethoxymethylene)oxazolone. Subsequent hydrolysis of the acetamido and ester substituents of the N-benzylpyridones was selectively performed to access unique beta-amino acid products. Formation of the mixed anhydride of this acid, followed by amide bond formation with the ester of an alpha-amino acid, allowed extension of the peptide chain from the dihydropyridone structure.

  DOI：

  10.1021/jo9600520
• 作为产物：
  描述：

  乙酰乙酰苄胺（AABA） 、 苄胺 在 iron(III) trifluoromethanesulfonate 作用下， 以 neat (no solvent) 为溶剂， 以66%的产率得到(Z)-N-benzyl-3-(benzylamino)but-2-enamide
  参考文献：
  名称：

  烯胺的氧化还原性质。

  摘要：

  烯胺是具有有趣的氧化还原特性的富电子化合物。在此，合成了由伯胺和β-酮羰基缩合而成的一系列仲烯胺，并通过循环伏安法系统地研究了它们的电化学氧化性能。此外，还进行了烯胺特别是那些催化中间体的氧化电位的理论计算，以进一步拓宽研究范围。揭示和讨论了可能的结构因素对氧化和所得自由基阳离子中间体的性质。探索了氧化还原电势与分子特性（例如最大占据分子轨道能量和自然种群分析电荷）的相关性，并且似乎没有简单的线性相关性。另一方面，与Mayr'的相关性很好 在一系列催化相关的烯胺中注意到其亲核参数N。自旋种群分析表明，烯胺自由基阳离子主要表现出碳中心自由基的特征。综合实验数据和计算数据，可以得出有关烯胺的氧化还原特性的全面图片，这将为氧化烯胺催化和转化的发展提供指导。

  DOI：

  10.1021/acs.joc.9b02003

文献信息

• COMPOSITIONS COMPRISING A POLYMERIC NETWORK
  申请人：UNIVERSITEIT GENT

  公开号：US20170327625A1

  公开（公告）日：2017-11-16

  The present invention relates to a composition comprising a polymeric network having at least one unit of formula (I), (II), and/or (III); (I) (II) (III) wherein said composition is obtained by contacting at least one compound A comprising at least two functions selected from the group of function of formula X—C(═O)—CHR 1 —C(═O)—R 2 , —C(═O)—C—R 2 ; or —C(═O)—CR 1 ═CR 2 —NR 4 R 5 ; wherein at least 25% by weight of compounds A have a functionality ≦5, with % by weight relative to the total weight of compounds A; with at least one compound B comprising at least one NH 2 , or NH 3 + groups; wherein X, R 1 , R 2 , R 3 , R 4 , R 5 , L 1 and L 2 have the same meaning as that defined in the claims. The present invention also relates to a compound comprising at least two units and at most 5 units of formula (I), (II), and/or (III); wherein R 1 , R 2 , R 3 , X, L 1 and L 2 have the same meaning as that defined in the claims. The present invention also relates to processes for preparing said composition and said compounds, to material, articles, and polymers comprising or using said compositions and compounds, and the use thereof.

  本发明涉及一种组合物，其包括至少一种具有式(I)、(II)和/或(III)的聚合网络单元；其中所述组合物是通过接触至少一种化合物A而获得的，所述化合物A包括至少两种选自以下功能组的功能：X—C(═O)—CHR1—C(═O)—R2，—C(═O)—C—R2；或—C(═O)—CR1═CR2—NR4R5；其中化合物A的至少25%的重量具有功能性≦5，以重量百分比相对于化合物A的总重量计算；以及至少一种包括至少一个NH2或NH3+基团的化合物B；其中X、R1、R2、R3、R4、R5、L1和L2的含义与权利要求书中定义的含义相同。本发明还涉及一种化合物，其包括至少两个单元和最多5个式(I)、(II)和/或(III)的单元；其中R1、R2、R3、X、L1和L2的含义与权利要求书中定义的含义相同。本发明还涉及制备所述组合物和所述化合物的方法，以及包括或使用所述组合物和化合物的材料、物品和聚合物，以及其用途。
• Compositions comprising a polymeric network
  申请人：UNIVERSITEIT GENT

  公开号：US10246548B2

  公开（公告）日：2019-04-02

  The present invention relates to a composition comprising a polymeric network having at least one unit of formula (I), (II), and/or (III); wherein the composition is obtained by contacting at least one compound A comprising at least two functions selected from the group of function of formula —X—C(═O)—CHR1-C(═O)—R2, —C(═O)—C≡C—R2; or —C(═O)—CR1═CR2—NR4R5; wherein at least 25% by weight of compounds A have a functionality ≤5, with % by weight relative to the total weight of compounds A; with at least one compound B comprising at least one —NH2, or —NH3+ groups; wherein X, R1, R2, R3, R4, R5, L1 and L2 have the same meaning as that defined in the claims. The present invention also relates to a compound comprising at least two units and at most 5 units of formula (I), (II), and/or (III), described hereinabove. The present invention also relates to processes for preparing the composition and the compounds, to material, articles, and polymers comprising or using the compositions and compounds, and the use thereof.

  本发明涉及一种组合物，该组合物由至少具有一个式（I）、（II）和/或（III）单元的聚合物网络组成； 其中该组合物是通过与至少一种化合物A接触而获得的，该化合物A包含至少两种选自式-X-C(═O)-CHR1-C(═O)-R2，-C(═O)-C≡C-R2；或-C(═O)-CR1═CR2-NR4R5的官能团；其中至少25%(重量)的化合物A的官能度≤5，以相对于化合物A总重量的%(重量)计；至少一种化合物B包含至少一个-NH2，或-NH3+基团；其中X、R1、R2、R3、R4、R5、L1和L2与权利要求书中所定义的含义相同。本发明还涉及一种包含至少两个单元和至多 5 个单元的式(I)、(II)和/或(III)化合物。本发明还涉及制备组合物和化合物的工艺，涉及包含或使用组合物和化合物的材料、物品和聚合物及其用途。
• EP3233978B1
  申请人：——

  公开号：EP3233978B1

  公开（公告）日：2021-03-03
• [EN] COMPOSITIONS COMPRISING A POLYMERIC NETWORK<br/>[FR] COMPOSITIONS COMPRENANT UN RÉSEAU POLYMÈRE
  申请人：UNIV GENT

  公开号：WO2016097169A1

  公开（公告）日：2016-06-23

  The present invention relates to a composition comprising a polymeric network having at least one unit of formula (I), (II), and/or (III); (I) (II) (III) wherein said composition is obtained by contacting at least one compound A comprising at least two functions selected from the group of function of formula X-C(=O)-CHR1-C(=O)-R2, -C(=O)-C -R2; or -C(=O)-CR1=CR2-NR4R5; wherein at least 25 % by weight of compounds A have a functionality ≤5, with % by weight relative to the total weight of compounds A; with at least one compound B comprising at least one NH2, or NH3+ groups; wherein X, R1, R2, R3, R4, R5, L1 and L2 have the same meaning as that defined in the claims. The present invention also relates to a compound comprising at least two units and at most 5 units of formula (I), (II), and/or (III); wherein R1, R2, R3, X, L1 and L2 have the same meaning as that defined in the claims. The present invention also relates to processes for preparing said composition and said compounds, to material, articles, and polymers comprising or using said compositions and compounds, and the use thereof.
• Formation of Dihydropyridone- and Pyridone-Based Peptide Analogs through Aza-Annulation of β-Enamino Ester and Amide Substrates with α-Amido Acrylate Derivatives
  作者：Lars G. Beholz、Petr Benovsky、Donald L. Ward、Nancy S. Barta、John R. Stille

  DOI：10.1021/jo9600520

  日期：1997.2.1

  The aza-annulation of beta-enamino ester and amide substrates with the mixed anhydride of 2-acetamidoacrylic acid was used for the efficient construction of highly substituted alpha-acetamido delta-lactam products. With the alpha-acetamido substituent, lactam functionality, and gamma-carboxylate group, these delta-lactam products represent an interesting class of conformationally restricted dipeptide analogs. The framework of this lactam hub is structurally related to that of an alpha-amino acid coupled with a beta-amino acid. When alpha-amino esters derived from naturally occurring amino acids were used in the enamine formation step, subsequent aza-annulation led to branched peptide surrogates with two C-termini that extended from a common N-terminus. Oxidation of the aza-annulation products resulted in the generation of a planar system with peptide functionality radiating from the 1, 3, and 5 positions of the pyridone hub. Alternatively, pyridone products could be formed directly from the enamino amides by reaction with 2-phenyl-4-(ethoxymethylene)oxazolone. Subsequent hydrolysis of the acetamido and ester substituents of the N-benzylpyridones was selectively performed to access unique beta-amino acid products. Formation of the mixed anhydride of this acid, followed by amide bond formation with the ester of an alpha-amino acid, allowed extension of the peptide chain from the dihydropyridone structure.