5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-7-phenyl-3-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hept-1-enyl]-9-oxa-tricyclo[3.3.1.03,7]non-1-yl}-pentanoic acid methyl ester | 141887-85-6

• 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: 5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-7-phenyl-3-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hept-1-enyl]-9-oxa-tricyclo[3.3.1.03,7]non-1-yl}-pentanoic acid methyl ester
• CAS: 141887-85-6
• 化学式: C₃₇H₄₄F₃IO₆
• 分子量: 768.652
• InChiKey: FCUAAKMQKSJQNQ-NUEXVLTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  47.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-7-phenyl-3-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hept-1-enyl]-9-oxa-tricyclo[3.3.1.03,7]non-1-yl}-pentanoic acid methyl ester 在 二叔丁基过氧化物 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 5-[(1S,3S,4S,5R,7R)-4-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxymethyl)-9-oxa-tricyclo[3.3.1.03,7]non-1-yl]-pentanoic acid methyl ester
  参考文献：
  名称：

  An azido-functionalized isocarbacyclin analogue acting as an efficient photoaffinity probe for a prostacyclin receptor

  摘要：

  A stable prostacyclin analogue, (15S)-18c, having an azidophenyl, group as a photoaffinity labeling functionality has been synthesized. This compound has a sufficiently high affinity to the prostacyclin receptor protein in mastocytoma P-815 cells, exhibiting an IC50 value of 3 nM for the replacement of iloprost bound to the receptor protein. A photoaffinity probe compound, [H-3]-(15S)-18c, is obtainable by reduction of the ketone 16c with [H-3]NaBH4-CeCl3 followed by alkaline hydrolysis of the methyl ester.

  DOI：

  10.1016/s0040-4020(01)88526-4
• 作为产物：
  描述：

  5-[(3aS,5R,6R,6aS)-5-Hydroxy-6-((E)-(S)-3-hydroxy-7-phenyl-hept-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid methyl ester 在 吡啶 、 碘 作用下， 以 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 3.58h， 生成 5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-7-phenyl-3-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hept-1-enyl]-9-oxa-tricyclo[3.3.1.03,7]non-1-yl}-pentanoic acid methyl ester
  参考文献：
  名称：

  An azido-functionalized isocarbacyclin analogue acting as an efficient photoaffinity probe for a prostacyclin receptor

  摘要：

  A stable prostacyclin analogue, (15S)-18c, having an azidophenyl, group as a photoaffinity labeling functionality has been synthesized. This compound has a sufficiently high affinity to the prostacyclin receptor protein in mastocytoma P-815 cells, exhibiting an IC50 value of 3 nM for the replacement of iloprost bound to the receptor protein. A photoaffinity probe compound, [H-3]-(15S)-18c, is obtainable by reduction of the ketone 16c with [H-3]NaBH4-CeCl3 followed by alkaline hydrolysis of the methyl ester.

  DOI：

  10.1016/s0040-4020(01)88526-4