N-(3-氨基-3-氧代-1-丙烯-2-基)苯甲酰胺 | 478932-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3-氨基-3-氧代-1-丙烯-2-基)苯甲酰胺
• 英文名称: N-(1-carbamoylvinyl)benzamide
• 英文别名: N-(1-Carbamoyl-vinyl)-benzamide；N-(3-amino-3-oxoprop-1-en-2-yl)benzamide
• CAS: 478932-11-5
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: CZVJSDGIWSVXMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-氨基-3-氧代-1-丙烯-2-基)苯甲酰胺 在 氢碘酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以84%的产率得到苯甲酰胺
  参考文献：
  名称：

  Mild Method for Cleavage of Dehydroalanine Units:  Highly Efficient Conversion of Nocathiacin I to Nocathiacin IV

  摘要：

  Thiazolyl peptide antibacterial nocathiacin I (1) was converted to nocathiacin IV (4) in high yield using iodomethane and hydriodic acid in THF at 45 degreesC. Several simplified dehydroalanine-containing systems undergo dehydroalanine cleavage under the same conditions, although in these cases iodomethane is not needed for efficient conversion. The mild reaction conditions are in contrast with other methods described in the literature.

  DOI：

  10.1021/jo0261698
• 作为产物：
  描述：

  2-benzoylaminoacrylic acid methyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以45%的产率得到N-(3-氨基-3-氧代-1-丙烯-2-基)苯甲酰胺
  参考文献：
  名称：

  Mild Method for Cleavage of Dehydroalanine Units:  Highly Efficient Conversion of Nocathiacin I to Nocathiacin IV

  摘要：

  Thiazolyl peptide antibacterial nocathiacin I (1) was converted to nocathiacin IV (4) in high yield using iodomethane and hydriodic acid in THF at 45 degreesC. Several simplified dehydroalanine-containing systems undergo dehydroalanine cleavage under the same conditions, although in these cases iodomethane is not needed for efficient conversion. The mild reaction conditions are in contrast with other methods described in the literature.

  DOI：

  10.1021/jo0261698

文献信息

• Cobalt(III)‐Catalyzed C−H Amidation of Dehydroalanine for the Site‐Selective Structural Diversification of Thiostrepton
  作者：Ryan J. Scamp、Edward deRamon、Eric K. Paulson、Scott J. Miller、Jonathan A. Ellman

  DOI：10.1002/anie.201911886

  日期：2020.1.7

  Thiostrepton is a potent antibiotic against a broad range of Gram-positive bacteria, but its medical applications have been limited by its poor aqueous solubility. In this work, the first C(sp2 )-H amidation of dehydroalanine (Dha) residues was applied to the site selective modification of thiostrepton to prepare a variety of derivatives. Unlike all prior methods for the modification of thiostrepton

  硫链丝菌素是一种针对多种革兰氏阳性菌的有效抗生素，但其医疗应用因其水溶性差而受到限制。本工作首次将脱氢丙氨酸(Dha)残基的C(sp2)-H酰胺化应用于硫链丝菌肽的位点选择性修饰，制备了多种衍生物。与所有现有的硫链丝菌肽修饰方法不同，Dha 残基的烯烃骨架得以保留，并且对 Z-立体异构体具有完全选择性。此外，通过 CH 酰胺化引入醛基，使肟连接能够安装更广泛的功能。硫链丝菌素衍生物通常保持抗菌活性，重要的是，其中八种衍生物的水溶性得到改善（高达 28 倍），从而解决了这种抗生素的一个关键缺点。CoIII 催化的 C(sp2 )-H Dha 酰胺化的特殊官能团相容性和位点选择性表明该方法可以推广到含有 Dha 残基的其他天然产物和生物聚合物。
• Mild Method for Cleavage of Dehydroalanine Units:  Highly Efficient Conversion of Nocathiacin I to Nocathiacin IV
  作者：Alicia Regueiro-Ren、Yasutsugu Ueda

  DOI：10.1021/jo0261698

  日期：2002.11.1

  Thiazolyl peptide antibacterial nocathiacin I (1) was converted to nocathiacin IV (4) in high yield using iodomethane and hydriodic acid in THF at 45 degreesC. Several simplified dehydroalanine-containing systems undergo dehydroalanine cleavage under the same conditions, although in these cases iodomethane is not needed for efficient conversion. The mild reaction conditions are in contrast with other methods described in the literature.