N-[(Benzyl-trimethylsilanylmethyl-carbamoyl)-methyl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-methyl-acetamide | 607741-01-5

• 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-[(Benzyl-trimethylsilanylmethyl-carbamoyl)-methyl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-methyl-acetamide
• 英文别名: N-[2-[benzyl(trimethylsilylmethyl)amino]-2-oxoethyl]-2-(1,3-dioxoisoindol-2-yl)-N-methylacetamide
• CAS: 607741-01-5
• 化学式: C₂₄H₂₉N₃O₄Si
• 分子量: 451.597
• InChiKey: CXDMVPIOJXEDLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(Benzyl-trimethylsilanylmethyl-carbamoyl)-methyl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-methyl-acetamide 在 四丁基氢氧化铵 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以40%的产率得到6-Benzyl-4b-hydroxy-9-methyl-5,6,8,9-tetrahydro-4bH-6,9,11a-triaza-cyclonona[a]indene-7,10,12-trione
  参考文献：
  名称：

  A Synthetic Strategy for the Preparation of Cyclic Peptide Mimetics Based on SET-Promoted Photocyclization Processes

  摘要：

  A novel method for the synthesis of cyclic peptide analogues has been developed. The general approach relies on the use of SET-promoted photocyclization reactions of peptides that contain N-terminal phthalimides as light absorbing electron acceptor moieties and C-terminal alpha-amidosilane or alpha-amidocarboxylate centers. Prototypical substrates are prepared by coupling preformed peptides with the acid chloride of N-phthalimidoglycine. Irradiation of these substrates results in the generation of cyclic peptide analogues in modest to good yields. The chemical efficiencies of these processes are not significantly affected by (1) the lengths of the peptide chains separating the phthalimide and alpha-amidosilane or alpha-amidocarboxylate centers and (2) the nature of the penultimate cation radical a-heterolytic fragmentation process (i.e., desilylation vs decarboxylation). An evaluation of the effects of N-alkyl substitution on the amide residues in the peptide chain showed that N-alkyl substitution does not have a major impact on the efficiencies of the photocyclization reactions but that it profoundly increases the stability of the cyclic peptide.

  DOI：

  10.1021/ja030297b
• 作为产物：
  描述：

  [(Benzyl-trimethylsilanylmethyl-carbamoyl)-methyl]-methyl-carbamic acid tert-butyl ester 在 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 N-[(Benzyl-trimethylsilanylmethyl-carbamoyl)-methyl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-methyl-acetamide
  参考文献：
  名称：

  A Synthetic Strategy for the Preparation of Cyclic Peptide Mimetics Based on SET-Promoted Photocyclization Processes

  摘要：

  A novel method for the synthesis of cyclic peptide analogues has been developed. The general approach relies on the use of SET-promoted photocyclization reactions of peptides that contain N-terminal phthalimides as light absorbing electron acceptor moieties and C-terminal alpha-amidosilane or alpha-amidocarboxylate centers. Prototypical substrates are prepared by coupling preformed peptides with the acid chloride of N-phthalimidoglycine. Irradiation of these substrates results in the generation of cyclic peptide analogues in modest to good yields. The chemical efficiencies of these processes are not significantly affected by (1) the lengths of the peptide chains separating the phthalimide and alpha-amidosilane or alpha-amidocarboxylate centers and (2) the nature of the penultimate cation radical a-heterolytic fragmentation process (i.e., desilylation vs decarboxylation). An evaluation of the effects of N-alkyl substitution on the amide residues in the peptide chain showed that N-alkyl substitution does not have a major impact on the efficiencies of the photocyclization reactions but that it profoundly increases the stability of the cyclic peptide.

  DOI：

  10.1021/ja030297b

文献信息

• A Synthetic Strategy for the Preparation of Cyclic Peptide Mimetics Based on SET-Promoted Photocyclization Processes
  作者：Ung Chan Yoon、Ying Xue Jin、Sun Wha Oh、Chan Hyo Park、Jong Hoon Park、Charles F. Campana、Xiaolu Cai、Eileen N. Duesler、Patrick S. Mariano

  DOI：10.1021/ja030297b

  日期：2003.9.1

  A novel method for the synthesis of cyclic peptide analogues has been developed. The general approach relies on the use of SET-promoted photocyclization reactions of peptides that contain N-terminal phthalimides as light absorbing electron acceptor moieties and C-terminal alpha-amidosilane or alpha-amidocarboxylate centers. Prototypical substrates are prepared by coupling preformed peptides with the acid chloride of N-phthalimidoglycine. Irradiation of these substrates results in the generation of cyclic peptide analogues in modest to good yields. The chemical efficiencies of these processes are not significantly affected by (1) the lengths of the peptide chains separating the phthalimide and alpha-amidosilane or alpha-amidocarboxylate centers and (2) the nature of the penultimate cation radical a-heterolytic fragmentation process (i.e., desilylation vs decarboxylation). An evaluation of the effects of N-alkyl substitution on the amide residues in the peptide chain showed that N-alkyl substitution does not have a major impact on the efficiencies of the photocyclization reactions but that it profoundly increases the stability of the cyclic peptide.