3-phenyl-2,3-dihydroimidazo[1,2-a]pyridine | 91954-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 3-phenyl-2,3-dihydroimidazo[1,2-a]pyridine
• 英文别名: 3-phenyl-2,3-dihydro-imidazo[1,2-a]pyridine；3-Phenyl-2,3-dihydro-imidazo[1,2-a]pyridin；3-Phenyl-2,3-dihydro-imidazo<1,2-a>pyridin；3-Phenyl-2,3-dihydro-pyrimidazol；3-Phenyl-2,3-dihydroimidazo[1,2-a]pyridine
• CAS: 91954-76-6
• 化学式: C₁₃H₁₂N₂
• 分子量: 196.252
• InChiKey: OENPWBMXGLKQGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  非尼拉朵 在 四甲基胍 作用下， 以 phosphate buffer 、 乙腈 为溶剂， 反应 9.0h， 生成 3-phenyl-2,3-dihydroimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Thermolytic Carbonates for Potential 5‘-Hydroxyl Protection of Deoxyribonucleosides

  摘要：

  Thermolytic groups structurally related to well-studied heat-sensitive phosphate/thiophosphate protecting groups have been evaluated for 5'-hydroxyl protection of deoxyribonucleosides as carbonates and for potential use in solid-phase oligonucleotide synthesis. The spatial arrangement of selected functional groups forming an asymmetric nucleosidic 5'-O-carbonic acid ester has been designed to enable heat-induced cyclodecarbonation reactions, which would result in the release of carbon dioxide and the generation of a nucleosidic 5'-hydroxyl group. The nucleosidic 5'-O-carbonates 3-8, 10-15, and 19-21 were prepared and were isolated in yields ranging from 45 to 83%. Thermolytic deprotection of these carbonates is preferably performed in aqueous organic solvent at 90 degreesC under near neutral conditions. The rates of carbonate deprotection are dependent on the nucleophilicity of the functional group involved in the postulated cyclodecarbonation reaction and on solvent polarity. Deprotection kinetics increase according to the following order: 4 < 5 < 10 < 6 < 12 < 7 < 13 < 8 < 14 congruent to 19-21 and CCl4 < dioxane < MeCN < t-BuOH < MeCN:phosphate buffer (3:1 v/v, pH 7.0) < EtOH:phosphate buffer (1:1 v/v, pH 7.0). Complete thermolytic deprotection of carbonates 7, 8, 13, and 14 is achieved within 20 min to 2 h under optimal conditions in phosphate buffer-MeCN. The 2-(2-pyridyl)amino-1-phenylethyl and 2-[N-methyl-N-(2-pyridyl)]aminoethyl groups are particularly promising for 5'-hydroxyl protection of deoxyribonucleosides as thermolytic carbonates.

  DOI：

  10.1021/jo035089g

文献信息

• Aminopyridines. II. The Preparation and Properties of 2-(Hydroxyalkylamino)-pyridines¹
  作者：Allan P. Gray、Donald E. Heitmeier、Ernest E. Spinner

  DOI：10.1021/ja01525a062

  日期：1959.8
• Reynaud et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 247, p. 2159
  作者：Reynaud et al.

  DOI：——

  日期：——
• Thermolytic Carbonates for Potential 5‘-Hydroxyl Protection of Deoxyribonucleosides
  作者：Marcin K. Chmielewski、Vicente Marchán、Jacek Cieślak、Andrzej Grajkowski、Victor Livengood、Ursula Münch、Andrzej Wilk、Serge L. Beaucage

  DOI：10.1021/jo035089g

  日期：2003.12.1

  Thermolytic groups structurally related to well-studied heat-sensitive phosphate/thiophosphate protecting groups have been evaluated for 5'-hydroxyl protection of deoxyribonucleosides as carbonates and for potential use in solid-phase oligonucleotide synthesis. The spatial arrangement of selected functional groups forming an asymmetric nucleosidic 5'-O-carbonic acid ester has been designed to enable heat-induced cyclodecarbonation reactions, which would result in the release of carbon dioxide and the generation of a nucleosidic 5'-hydroxyl group. The nucleosidic 5'-O-carbonates 3-8, 10-15, and 19-21 were prepared and were isolated in yields ranging from 45 to 83%. Thermolytic deprotection of these carbonates is preferably performed in aqueous organic solvent at 90 degreesC under near neutral conditions. The rates of carbonate deprotection are dependent on the nucleophilicity of the functional group involved in the postulated cyclodecarbonation reaction and on solvent polarity. Deprotection kinetics increase according to the following order: 4 < 5 < 10 < 6 < 12 < 7 < 13 < 8 < 14 congruent to 19-21 and CCl4 < dioxane < MeCN < t-BuOH < MeCN:phosphate buffer (3:1 v/v, pH 7.0) < EtOH:phosphate buffer (1:1 v/v, pH 7.0). Complete thermolytic deprotection of carbonates 7, 8, 13, and 14 is achieved within 20 min to 2 h under optimal conditions in phosphate buffer-MeCN. The 2-(2-pyridyl)amino-1-phenylethyl and 2-[N-methyl-N-(2-pyridyl)]aminoethyl groups are particularly promising for 5'-hydroxyl protection of deoxyribonucleosides as thermolytic carbonates.