5-{(3aS,5R,6R,6aS)-6-[(E)-(S)-7-(3-Amino-phenyl)-3-hydroxy-hept-1-enyl]-5-hydroxy-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid methyl ester | 141887-82-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-{(3aS,5R,6R,6aS)-6-[(E)-(S)-7-(3-Amino-phenyl)-3-hydroxy-hept-1-enyl]-5-hydroxy-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid methyl ester
• CAS: 141887-82-3
• 化学式: C₂₇H₃₉NO₄
• 分子量: 441.611
• InChiKey: RUVYCYNBZUUURI-CMEURKNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  32.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  92.78
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-{(3aS,5R,6R,6aS)-6-[(E)-(S)-7-(3-Amino-phenyl)-3-hydroxy-hept-1-enyl]-5-hydroxy-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid methyl ester 在 碘 、 亚膦酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 0.41h， 生成 5-[(1R,2R,3S,5R,6R,7R)-6-((E)-(S)-3-Hydroxy-7-phenyl-hept-1-enyl)-2-iodo-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：

  19-(3-azidophenyl)-15-dehydro-20-norisocarbacyclin methyl ester 在 palladium on activated charcoal sodium tetrahydroborate 、 cerium(III) chloride 、 氢气 作用下， 以 甲醇 为溶剂， 反应 7.22h， 生成 5-{(3aS,5R,6R,6aS)-6-[(E)-(S)-7-(3-Amino-phenyl)-3-hydroxy-hept-1-enyl]-5-hydroxy-1,3a,4,5,6,6a-hexahydro-pentalen-2-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