N-{4-[N-(2-phenylethan-1-yl)carbamoyl]phenyl}phthalimide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-{4-[N-(2-phenylethan-1-yl)carbamoyl]phenyl}phthalimide
• 英文别名: 4-(1,3-dioxoisoindol-2-yl)-N-(2-phenylethyl)benzamide
• 化学式: C₂₃H₁₈N₂O₃
• 分子量: 370.408
• InChiKey: FFDCHHZDCULHOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-羰苯基)酞亚酸 在 三乙基硅烷 、 palladium on activated charcoal 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 25.22h， 生成 N-{4-[N-(2-phenylethan-1-yl)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

• Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives
  作者：Margareta Sohora、Tatjana Šumanovac Ramljak、Kata Mlinarić-Majerski、Nikola Basarić

  DOI：10.5562/cca2482

  日期：——

  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.