2-((4S,13S)-13-Amino-2,7-dioxo-15-oxa-3,8,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-thiazole-4-carboxylic acid | 474686-39-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 2-((4S,13S)-13-Amino-2,7-dioxo-15-oxa-3,8,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-thiazole-4-carboxylic acid
• CAS: 474686-39-0
• 化学式: C₁₇H₂₁N₅O₅S
• 分子量: 407.45
• InChiKey: FIJATCFJEMNJNO-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  160.44
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-((4S,13S)-13-Amino-2,7-dioxo-15-oxa-3,8,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-thiazole-4-carboxylic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以78%的产率得到(1S,8S,17S,24S)-37,45-dioxa-3,19-dithia-7,13,23,29,33,39,40,41,47,48-decazaheptacyclo[22.8.6.68,17.12,5.118,21.135,38.143,46]octatetraconta-2(47),4,18(40),20,35,38,43,46(48)-octaene-6,14,22,30,34,42-hexone
  参考文献：
  名称：

  Regioselective Synthesis of Antiparallel Loops on a Macrocyclic Scaffold Constrained by Oxazoles and Thiazoles

  摘要：

  [GRAPHICS]The regioselective syntheses and structures are reported for two tris-macrocylic compounds, each possessing two antiparallel loops on a macrocyclic scaffold constrained by two oxazoles and two thiazoles. NMR solution structures show the loops projecting from the same face of the macrocycle. Such molecules are shown to be prototypes for mimicking multiple loops of proteins.

  DOI：

  10.1021/ol026463m
• 作为产物：
  描述：

  2-((4S,13S)-13-Benzyloxycarbonylamino-2,7-dioxo-15-oxa-3,8,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-thiazole-4-carboxylic acid 在 对甲酚 、 氢氟酸 作用下， 以90%的产率得到2-((4S,13S)-13-Amino-2,7-dioxo-15-oxa-3,8,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-thiazole-4-carboxylic acid
  参考文献：
  名称：

  Regioselective Synthesis of Antiparallel Loops on a Macrocyclic Scaffold Constrained by Oxazoles and Thiazoles

  摘要：

  [GRAPHICS]The regioselective syntheses and structures are reported for two tris-macrocylic compounds, each possessing two antiparallel loops on a macrocyclic scaffold constrained by two oxazoles and two thiazoles. NMR solution structures show the loops projecting from the same face of the macrocycle. Such molecules are shown to be prototypes for mimicking multiple loops of proteins.

  DOI：

  10.1021/ol026463m