(3aR,4R,5R,6aS)-hexahydro-4-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)-2H-cyclopenta[b]furan-2-ol | 856453-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (3aR,4R,5R,6aS)-hexahydro-4-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)-2H-cyclopenta[b]furan-2-ol
• 英文别名: (3aR,4R,5R,6aS)-hexahydro-4-((S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)-2H-cyclopenta[b]furan-2-ol；(3aR,4R,5R,6aS)-hexahydro-4-((S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy) pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)-2H-cyclopenta[b]furan-2-ol；(3aR,4R,5R,6aS)-5-(oxan-2-yloxy)-4-[(E,3S)-3-(oxan-2-yloxy)-5-phenylpent-1-enyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]furan-2-ol
• CAS: 856453-32-2
• 化学式: C₂₈H₄₀O₆
• 分子量: 472.622
• InChiKey: DFVFLVBKEFXAHN-LREJKMIYSA-N

物化性质

• 沸点：
  626.0±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,4R,5R,6aS)-hexahydro-4-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)-2H-cyclopenta[b]furan-2-ol 在 jones reagent 、 sodium methylsulfinylcarbanide 作用下， 以 丙酮 为溶剂， 反应 2.08h， 生成 N-{(Z)-7-[(1R,2R,3R)-5-Oxo-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoyl}-methanesulfonamide
  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)-hexahydro-4-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)cyclopenta[b]furan-2-one 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 生成 (3aR,4R,5R,6aS)-hexahydro-4-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)-2H-cyclopenta[b]furan-2-ol
  参考文献：
  名称：

  PROCESSES AND INTERMEDIATES FOR THE PREPARATIONS OF ISOMER FREE PROSTAGLANDINS

  摘要：

  提供了一种用于制备基本上不含5,6-顺式异构体的化合物I-2的新工艺：其中R2、R3和R4如规范中定义。还提供了用于制备无异构体前列腺素及其衍生物的新中间体。

  公开号：

  US20150051410A1

文献信息

• Method for preparing prostaglandin F analogue
  申请人：Yao Chi-Hsiang

  公开号：US20090259066A1

  公开（公告）日：2009-10-15

  A method for preparing a prostaglandin F analogue represented by the following formula (I) is disclosed, wherein R 1 , and are as defined in the specification.

  公开了一种制备以下式(I)所表示的前列腺素F类似物的方法，其中R1和R2如规范中所定义。
• Processes for the preparation of isomer free prostaglandins
  申请人：Chirogate International Inc.

  公开号：EP2837621A1

  公开（公告）日：2015-02-18

  Novel processes for the preparation of a compound of Formula I-2 substantially free of the 5,6-trans isomer: wherein R2, R3 and R4 are as defined in the specification are provided. Novel intermediates for the preparations of isomer free Prostaglandins and derivatives thereof are also provided.

  制备基本不含 5,6-反式异构体的式 I-2 化合物的新工艺： 其中 R2、R3 和 R4 如说明书中所定义。还提供了制备不含异构体的前列腺素及其衍生物的新型中间体。
• Processes and intermediates for the preparations of isomer free prostaglandins
  申请人：Chirogate International Inc.

  公开号：EP2837621B1

  公开（公告）日：2019-12-25
• [EN] PROSTAGLANDIN SYNTHESIS<br/>[FR] SYNTHESE DE LA PROSTAGLANDINE
  申请人：JOHNSON MATTHEY PLC

  公开号：WO2005058812A3

  公开（公告）日：2005-10-13
• JOHNSON, M. R.;SCHAAF, T. K.;HESS, H. -J. E.
  作者：JOHNSON, M. R.、SCHAAF, T. K.、HESS, H. -J. E.

  DOI：——

  日期：——