(2S)-N-(3-hydroxybenzyl)-2-<3-(4-iodophenyl)propionamido>propionamide | 147949-88-0

• 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: (2S)-N-(3-hydroxybenzyl)-2-<3-(4-iodophenyl)propionamido>propionamide
• 英文别名: (2S)-N-(3-hydroxybenzyl)-2-[3-(4-iodophenyl)propionamido]propionamide；(2S)-N-[(3-hydroxyphenyl)methyl]-2-[3-(4-iodophenyl)propanoylamino]propanamide
• CAS: 147949-88-0
• 化学式: C₁₉H₂₁IN₂O₃
• 分子量: 452.292
• InChiKey: GZQGMVPZKQNPOX-ZDUSSCGKSA-N

物化性质

• 沸点：
  694.4±55.0 °C(predicted)
• 密度：
  1.516±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-N-(3-hydroxybenzyl)-2-<3-(4-iodophenyl)propionamido>propionamide 在 吡啶 、 sodium hydride 作用下， 生成 (11S)-10,13-Dioxo-2-oxa-11-methyl-9,12-diazatricyclo<14.2.2.1^3,7>heneicosa-3,5,7(21),16,18,19-hexaene 、 (11R)-10,13-Dioxo-2-oxa-11-methyl-9,12-diazatricyclo<14.2.2.1^3,7>heneicosa-3,5,7(21),16,18,19-hexaene
  参考文献：
  名称：

  Vancomycin and ristocetin models: synthesis via the Ullmann macrocyclization reaction

  摘要：

  The preparations of 2 and 3, the parent skeletons of the CD and DE diphenyl ether 16-membered ring systems of vancomycin and ristocetin, based on the implementation of an intramolecular Ullmann macrocyclization reaction are detailed. Additional studies which define the scope of substrates suitable for use in the Ullmann macrocyclization reaction are described including a limited study of those bearing centers capable of racemization. Within the limited series of agents examined, Ullmann macrocyclization closure of the DE ring system was found to occur at a faster rate and in higher overall yields than those providing the CD ring system. N-Methylation of the amide linking chain decelerates or inhibits Ullmann macrocyclization and a-substitution of the central amino acid of the linking chain significantly increases the cyclization conversions. Racemization of the central amino acid of the linking amide chain was found to be minimal (5%) under reaction conditions where the secondary amides are deliberately deprotonated prior to exposure of the substrate to the thermal, basic reaction conditions.

  DOI：

  10.1021/jo00058a024
• 作为产物：
  描述：

  3-(4-碘苯基)丙酸 在 氯甲酸乙酯 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.42h， 生成 (2S)-N-(3-hydroxybenzyl)-2-<3-(4-iodophenyl)propionamido>propionamide
  参考文献：
  名称：

  Vancomycin and ristocetin models: synthesis via the Ullmann macrocyclization reaction

  摘要：

  The preparations of 2 and 3, the parent skeletons of the CD and DE diphenyl ether 16-membered ring systems of vancomycin and ristocetin, based on the implementation of an intramolecular Ullmann macrocyclization reaction are detailed. Additional studies which define the scope of substrates suitable for use in the Ullmann macrocyclization reaction are described including a limited study of those bearing centers capable of racemization. Within the limited series of agents examined, Ullmann macrocyclization closure of the DE ring system was found to occur at a faster rate and in higher overall yields than those providing the CD ring system. N-Methylation of the amide linking chain decelerates or inhibits Ullmann macrocyclization and a-substitution of the central amino acid of the linking chain significantly increases the cyclization conversions. Racemization of the central amino acid of the linking amide chain was found to be minimal (5%) under reaction conditions where the secondary amides are deliberately deprotonated prior to exposure of the substrate to the thermal, basic reaction conditions.

  DOI：

  10.1021/jo00058a024