methyl N-[3-phenyl-1-oxo-2-propen-1-yl] glycinate | 40778-04-9

• 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: methyl N-[3-phenyl-1-oxo-2-propen-1-yl] glycinate
• 英文别名: N-cinnamoyl-glycine methyl ether；N-Cinnamoyl-glycin-methylester；Cinnamoylglycinmethylester；Glycine,n-(1-oxo-3-phenyl-2-propen-1-yl)-, methyl ester；methyl 2-(3-phenylprop-2-enoylamino)acetate
• CAS: 40778-04-9
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: XFAGPDNLMRNSRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-[3-phenyl-1-oxo-2-propen-1-yl] glycinate 在 一水合肼 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 (E)-N-(5-Hydroxy-1H-pyrazol-4-yl)-3-phenyl-acrylamide
  参考文献：
  名称：

  Singh; Singh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 9, p. 688 - 693

  摘要：

  DOI：
• 作为产物：
  描述：

  甘氨酸甲酯盐酸盐 、 肉桂酸 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 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以90.2%的产率得到methyl N-[3-phenyl-1-oxo-2-propen-1-yl] glycinate
  参考文献：
  名称：

  Tyrosinase inhibitory effects and antioxidative activities of novel cinnamoyl amides with amino acid ester moiety

  摘要：

  Nine cinnamoyl amides with amino acid ester (CAAE) moiety were synthesized by the conjugation of the corresponding cinnamic acids (cinnamic acid, 4-hydroxy cinnamic acid, ferulic acid and caffeic acid) with amino acid esters, and their inhibitory effects on the activities of mushroom tyrosinase were investigated, using L-3,4-dihydroxyl-phenylalanine (L-DOPA) as the substrate. Among these CAAE amides, ethyl N-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-L-phenylalaninate (b(4)) showed the strongest inhibitory activity; the IC50 was 0.18 mu M. The IC50 values, inhibition types, inhibition mechanisms and kinetics of all these CAAE amides were evaluated. A structure-activity relationship (SAR) study found that the inhibitory effects were potentiated with the increasing length of hydrocarbon chains at the amino acid esters and also influenced by the substituents at the styrene groups. Furthermore, the hydroxyl radical scavenging and anti-lipid peroxidation activities of four CAAE derivatives were also investigated. Among these compounds, b(3) (ethyl N-[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-L-phenylalaninate) and b(4) exhibited potential antioxidant activities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2012.03.021

文献信息

• Derivatives of L-proline, their preparation and their biological uses
  申请人：Inorgan SA Recherche & Developpement Pharmaceutiques, CAS

  公开号：US05212158A1

  公开（公告）日：1993-05-18

  The L-proline derivatives of the invention correspond to the Formula I: ##STR1## in which R.sub.1 corresponds to the Formula II: ##STR2## in which R is a carbonyl group, an acyl group --Y--CO-- or an oxy-acyl group --O--Y--CO--, Y being an alkyl or an alkenyl chain, Z being one or more hydrogen atoms, or one or more substituents chosen from among halogen atoms, CF.sub.3, alkyl or alkoxy groups and an alkylenedioxy group in the case of two neighbouring substituents, R.sub.2 is --NH.sub.2, --OH, or a derivative of these groups, A.sub.1 and A.sub.2 are amino acid residues and B.sub.1 and B.sub.2 represents a hydrogen atom or a methyl group, and the pharmacologically acceptable salts of these derivatives. These derivatives are useful particularly as the active principles of medicines possessing, in particular, a nootropic action.

  本发明的L-脯氨酸衍生物对应于公式I：##STR1## 其中R.sub.1对应于公式II：##STR2## 其中R是一个羰基基团，一个酰基--Y--CO--或一个氧酰基--O--Y--CO--，其中Y是一个烷基或烯基链，Z是一个或多个氢原子，或一个或多个从卤素原子，CF.sub.3，烷基或烷氧基和两个相邻取代基的烷二氧基基团中选择的取代基，R.sub.2是--NH.sub.2，--OH或这些基团的衍生物，A.sub.1和A.sub.2是氨基酸残基，B.sub.1和B.sub.2代表氢原子或甲基基团，以及这些衍生物的药学上可接受的盐。这些衍生物特别有用作具有神经保护作用的药物的活性成分。
• Cinnamic acid derivative
  申请人：Seikagaku Kogyo Kabushiki Kaisha (Seikagaku Corporation)

  公开号：US06025444A1

  公开（公告）日：2000-02-15

  The invention provides a cinnamic acid derivative having a novel spacer introduced into cinnamic acid which is photodimerizable, a cinnamic acid-polysaccharide derivative photocurable with high sensitivity and efficiency obtainable by introducing the above cinnamic acid derivative into a host polysaccharide such as a glycosaminoglycan, and a photocrosslinked cinnamic acid-polysaccharide derivative obtainable by exposing the same cinnamic acid-polysaccharide derivative to ultraviolet light irradiation.

  本发明提供了一种在肉桂酸中引入新型间隔物的肉桂酸衍生物，该衍生物具有光二聚性；通过将上述肉桂酸衍生物引入宿主多糖（例如一种糖胺聚糖）中，可获得高灵敏度和高效性的肉桂酸-多糖衍生物光固化物；将同一肉桂酸-多糖衍生物暴露于紫外线照射下，可获得光交联的肉桂酸-多糖衍生物。
• Cyrene: a bio-based solvent for the Mizoroki–Heck reaction of aryl iodides
  作者：Naya A. Stini、Petros L. Gkizis、Christoforos G. Kokotos

  DOI：10.1039/d2ob02012b

  日期：——

  widely used organic reactions. Cyrene has appeared to be an excellent alternative solvent for a number of organic reactions. In this work, the development of a new, greener and more economical protocol for the Mizoroki–Heck reaction is described, using Cyrene as the green solvent and Pd/C as the palladium catalyst source. A wide substrate scope for the coupling of aryl iodides with acrylamides, acrylates

  开发更绿色和更可持续的方法，以及使现有协议适应更环保的程序，已成为有机合成的关键。引入和利用更环保的溶剂是一种非常有前途的替代品，特别是当它们可以在已知和广泛使用的有机反应中替代有毒有机溶剂时。Cyrene 似乎是许多有机反应的极佳替代溶剂。在这项工作中，描述了一种新的、更环保、更经济的 Mizoroki–Heck 反应方案的开发，使用 Cyrene 作为绿色溶剂，Pd/C 作为钯催化剂源。展示了芳基碘与丙烯酰胺、丙烯酸酯、丙烯酸、丙烯腈和苯乙烯偶联的广泛底​​物范围。Cyrene 的可回收性和最终产品中钯的浸出进行了检查，以提高该协议的工业适用性。此外，还报道了天然产物哌洛汀 A 的合成。
• Wei; Jiang; Zhang, Asian Journal of Chemistry, 2012, vol. 24, # 6, p. 2383 - 2388
  作者：Wei、Jiang、Zhang、Zhang、Guo

  DOI：——

  日期：——
• Singh; Singh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 9, p. 688 - 693
  作者：Singh、Singh

  DOI：——

  日期：——