(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-4-m-tolyloxy-but-1-enyl]-hexahydro-cyclopenta[b]furan-2-ol | 79124-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-4-m-tolyloxy-but-1-enyl]-hexahydro-cyclopenta[b]furan-2-ol
• CAS: 79124-53-1
• 化学式: C₂₈H₄₀O₇
• 分子量: 488.621
• InChiKey: DLDZZKPYTNJRHH-VTPCGUGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-4-m-tolyloxy-but-1-enyl]-hexahydro-cyclopenta[b]furan-2-ol 在 jones reagent 、 sodium methylsulfinylcarbanide 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 16.08h， 生成 N-(methanesulfonyl)-16-(m-methylphenoxy)-ω-tetranor-PGE2-carboxamide
  参考文献：
  名称：

  N-(Methanesulfonyl)-16-phenoxyprostaglandin carboxamides: tissue-selective, uterine stimulants

  摘要：

  In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro models. Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-omega-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).

  DOI：

  10.1021/jm00143a018
• 作为产物：
  描述：

  (3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3R)-3-hydroxy-4-(3-methylphenoxy)but-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.83h， 生成 (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-4-m-tolyloxy-but-1-enyl]-hexahydro-cyclopenta[b]furan-2-ol
  参考文献：
  名称：

  N-(Methanesulfonyl)-16-phenoxyprostaglandin carboxamides: tissue-selective, uterine stimulants

  摘要：

  In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro models. Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-omega-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).

  DOI：

  10.1021/jm00143a018