N-{4-[N-(carboxymethyl)carbamoyl]phenyl}phthalimide | 115978-01-3

• 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: N-{4-[N-(carboxymethyl)carbamoyl]phenyl}phthalimide
• 英文别名: 2-(4-(1,3-dioxoisoindolin-2-yl)benzamido)acetic acid；Glycine, N-[4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)benzoyl]-；2-[[4-(1,3-dioxoisoindol-2-yl)benzoyl]amino]acetic acid
• CAS: 115978-01-3
• 化学式: C₁₇H₁₂N₂O₅
• 分子量: 324.293
• InChiKey: ZXHHFWIHGLCKOP-UHFFFAOYSA-N

物化性质

• 密度：
  1.485±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-{4-[N-(carboxymethyl)carbamoyl]phenyl}phthalimide 在 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.17h， 以15%的产率得到N-{4-[(N-methyl)carbamoyl]phenyl}phthalimide
  参考文献：
  名称：

  Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives

  摘要：

  New dipeptide derivatives 1 and 3 were synthesized and their reactivity in the photochemical reaction of decarboxylation was investigated. The photodecarboxylation of N-adamantyl derivatives la and 1b and N-phenylphthalimide derivatives 3a and 3b probably takes place from the triplet excited state. The triplet excited state of la, 3a and 3b was characterized by laser flash photolysis. N-phenylphthalimides 3a and 3b undergo 2-5 times more efficient photodecarboxylation than N-adamantylphthalimides la and lb. The aminoacid residue (Phe or Gly) at the C-terminus of the dipeptide does not influence the photodecarboxylation efficiency. Product selectivity in the photoreactions is determined by the conformation of the molecules. N-phenylphthalimides with the separated electron donor (carboxylate) and acceptor moiety (phthalimide) give only simple decarboxylation products, whereas N-adamantyl derivatives also give cyclization products.

  DOI：

  10.5562/cca2482
• 作为产物：
  描述：

  N-(4-羰苯基)酞亚酸 在 三乙基硅烷 、 palladium on activated charcoal 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.17h， 生成 N-{4-[N-(carboxymethyl)carbamoyl]phenyl}phthalimide
  参考文献：
  名称：

  Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives

  摘要：

  New dipeptide derivatives 1 and 3 were synthesized and their reactivity in the photochemical reaction of decarboxylation was investigated. The photodecarboxylation of N-adamantyl derivatives la and 1b and N-phenylphthalimide derivatives 3a and 3b probably takes place from the triplet excited state. The triplet excited state of la, 3a and 3b was characterized by laser flash photolysis. N-phenylphthalimides 3a and 3b undergo 2-5 times more efficient photodecarboxylation than N-adamantylphthalimides la and lb. The aminoacid residue (Phe or Gly) at the C-terminus of the dipeptide does not influence the photodecarboxylation efficiency. Product selectivity in the photoreactions is determined by the conformation of the molecules. N-phenylphthalimides with the separated electron donor (carboxylate) and acceptor moiety (phthalimide) give only simple decarboxylation products, whereas N-adamantyl derivatives also give cyclization products.

  DOI：

  10.5562/cca2482

文献信息

• Synthesis and Biological Evaluation of New Multifunctional Oxazolone Scaffolds Incorporating Phenyl Benzoate Moiety
  作者：Ebrahim Abdel-Galil、Evelin B. Moawad、Ahmed El-Mekabaty、Gehad E. Said

  DOI：10.1002/jhet.3139

  日期：2018.5

  Oxazolone derivative 3a was utilized as a versatile precursor for the construction of new heterocyclic scaffolds containing imidazole, oxazine, triazine, and triazole rings (compounds 20, 21, 23, and 24, respectively). Furthermore, 4‐aminohippuric acid (2b) was used in the synthesis of various new oxazolone derivatives (13–19) by utilizing of its amino group in several transformations followed by heterocyclization

  恶唑酮衍生物3a中被（化合物用作含咪唑，恶嗪，三嗪，和三唑环新杂环的支架的结构的多功能前体20，21，23，和24分别）。此外，4-氨基马尿酸（图2b）中的溶液在各种新的恶唑酮衍生物（的合成中使用13 - 19）通过在几个变换其氨基的利用随后用醛这些化合物的heterocyclization 1通过经典的Erlenmeyer缩合方法得到目标恶唑酮。上这些化合物作为抗氧化剂和抗菌剂的评价，化合物20和24表现出良好的抗氧化活性，而化合物20，23和24表现出对良好的抗菌活性的大肠杆菌和金黄色葡萄球菌。