methyl (1R,5S,6S,7R)-6-formyl-7-hydroxybicyclo<3.3.0>oct-2-ene-3-pentanoate | 140900-71-6

• 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: methyl (1R,5S,6S,7R)-6-formyl-7-hydroxybicyclo<3.3.0>oct-2-ene-3-pentanoate
• 英文别名: methyl 5-[(3aS,5R,6R,6aS)-6-formyl-5-hydroxy-1,3a,4,5,6,6a-hexahydropentalen-2-yl]pentanoate
• CAS: 140900-71-6
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: VWANFJZNYLSARW-IGQOVBAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1R,5S,6S,7R)-6-formyl-7-hydroxybicyclo<3.3.0>oct-2-ene-3-pentanoate 在 palladium on activated charcoal sodium tetrahydroborate 、 cerium(III) chloride 、 氢气 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 7.22h， 生成 5-{(3aS,5R,6R,6aS)-6-[(S)-7-(3-Amino-phenyl)-3-hydroxy-heptyl]-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
• 作为产物：
  描述：

  13,14-dihydroxy-13,14-dihydroisocarbacyclin methyl ester 在 sodium periodate 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 1.0h， 生成 methyl (1R,5S,6S,7R)-6-formyl-7-hydroxybicyclo<3.3.0>oct-2-ene-3-pentanoate
  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

文献信息

• Suzuki, Masaaki; Kato, Koichi; Noyori, Ryoji, Angewandte Chemie, 1996, vol. 108, # 3, p. 366 - 369
  作者：Suzuki, Masaaki、Kato, Koichi、Noyori, Ryoji、Watanabe, Yumiko、Takechi, Hajime、et al.

  DOI：——

  日期：——