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 | 141887-84-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 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
• CAS: 141887-84-5
• 化学式: C₂₇H₃₇IO₄
• 分子量: 552.493
• InChiKey: TVONLCRCVMBUQU-QFSYUIGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  32.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  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 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 5-[(1R,2R,3S,5R,6S,7R)-2-Iodo-6-((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：

  11,15-O-bisacetyl-13,14-epoxy-13,14-dihydroisocarbacyclin methyl ester 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium periodate 、 cerium(III) chloride 、 水 、 氢气 、 碘 、 亚膦酸 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 苯 为溶剂， 反应 11.3h， 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