(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 | 69610-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 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)cyclopenta[b]furan-2-one
• 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)cyclopenta[b]furan-2-one；(3aR, 4R, 5R, 6aS) Hexahydro-4-[(E)-(3S)-5-phenyl-3-(tetrahydropyran-2-yloxy)-1-pentenyl]-5-(tetrahydropyran-2-yloxy)-2H-cyclopenta[b]furan-2-one；(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-hexahydrocyclopenta[b]furan-2-one
• CAS: 69610-63-5
• 化学式: C₂₈H₃₈O₆
• 分子量: 470.606
• InChiKey: QEEIJGHAVJKRHH-FFJKWTLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 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)cyclopenta[b]furan-2-one 在 potassium tert-butylate 、 二异丁基氢化铝 、 苯甲酰氯 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 36.84h， 生成 比马前列素
  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
• 作为产物：
  描述：

  3-苯丙酸甲酯 在 甲醇 、 lithium aluminium tetrahydride 、 正丁基锂 、 (-)-(S)-BINAL-H 、 sodium hexamethyldisilazane 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 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)cyclopenta[b]furan-2-one
  参考文献：
  名称：

  Synthesis and in vitro evaluation of human FP-receptor selective prostaglandin analogues

  摘要：

  The in vitro evaluation of a series of saturated prostaglandins revealed that compounds with omega chain aromatic rings retain nanomolar potency for the human prostaglandin F receptor (hFP receptor), exemplified by compound 8. In contrast, the double bonds are required for activity in the series with an acyclic omega chain as in PGF(2 alpha). (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(00)00273-0

文献信息

• Use of 9-deoxy prostaglandin derivatives to treat glaucoma
  申请人：Alcon Laboratories, Inc.

  公开号：US05698733A1

  公开（公告）日：1997-12-16

  Disclosed are 9-deoxyprostaglandins which are useful in the treatment of glaucoma and ocular hypertension. Some of these 9-deoxyprostaglandins are novel. Also disclosed are ophthalmic, pharmaceutical compositions comprising such prostaglandins.

  本发明涉及一种可用于治疗青光眼和眼压增高的9-去氧前列腺素。其中一些9-去氧前列腺素是新颖的。本发明还涉及包含这种前列腺素的眼科、制药组合物。
• 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
• N-(Methanesulfonyl)-16-phenoxyprostaglandin carboxamides: tissue-selective, uterine stimulants
  作者：Thomas K. Schaaf、Jasjit S. Bindra、James F. Eggler、Jacob J. Plattner、A. James Nelson、M. Ross Johnson、Jay W. Constantine、Hans-Juergen Hess、Walter Elger

  DOI：10.1021/jm00143a018

  日期：1981.11

  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).
• 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：——