(3aR,4R,5R,6aS)-5-Hydroxy-4-vinyl-hexahydro-cyclopenta[b]furan-2-one | 906000-90-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aR,4R,5R,6aS)-5-Hydroxy-4-vinyl-hexahydro-cyclopenta[b]furan-2-one
• 英文别名: (3aR,4R,5R,6aS)-4-ethenyl-5-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS: 906000-90-6
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: FOIIZBCBQCDEKU-XUTVFYLZSA-N

物化性质

• 沸点：
  294.5±40.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,4R,5R,6aS)-5-Hydroxy-4-vinyl-hexahydro-cyclopenta[b]furan-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 咪唑 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Effect of allylic and homoallylic substituents on cross metathesis: syntheses of prostaglandins F2α and J2

  摘要：

  We describe the effect of allylic (C15) and homoallylic (C11) substituents on cross metathesis reactions with Corey lactone derivatives. This strategy has led to the successful syntheses of PGF(2 alpha) and PGJ(2). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.140
• 作为产物：
  描述：

  [3aR(3aα,4α,5β,6aα)]-(-)-5-(苯甲酰氧基)六氢-2-氧代-2H-环戊并[b]呋喃-4-甲醛 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (3aR,4R,5R,6aS)-5-Hydroxy-4-vinyl-hexahydro-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  Effect of allylic and homoallylic substituents on cross metathesis: syntheses of prostaglandins F2α and J2

  摘要：

  We describe the effect of allylic (C15) and homoallylic (C11) substituents on cross metathesis reactions with Corey lactone derivatives. This strategy has led to the successful syntheses of PGF(2 alpha) and PGJ(2). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.140

文献信息

• PROCESSES AND INTERMEDIATES FOR THE PREPARATIONS OF ISOMER FREE PROSTAGLANDINS
  申请人：CHIROGATE INTERNATIONAL INC.

  公开号：US20170015646A1

  公开（公告）日：2017-01-19

  Novel processes for the preparation of a compound of Formula I-2 substantially free of the 5,6-trans isomer: wherein R 2 , R 3 and R 4 are as defined in the specification are provided. Novel intermediates for the preparations of isomer free Prostaglandins and derivatives thereof are also provided.

  提供了制备公式I-2化合物的新工艺，该化合物基本上不含5,6-顺反异构体，其中R2，R3和R4如规范所定义。还提供了制备无异构体前列腺素及其衍生物的新中间体。
• METHOD FOR PRODUCING PKROSTAGLANDIN
  申请人：KYOWA PHARMA CHEMICAL CO., LTD.

  公开号：US20220169600A1

  公开（公告）日：2022-06-02

  The present invention provides a method for producing a compound represented by Formula (1a), (1b), or (1c), comprising a step of reducing a compound represented by Formula (3) in the presence of a metal complex represented by Formula (5), an inorganic base, and a solvent under a hydrogen atmosphere to obtain a compound represented by Formula (4). In the formula, Ar 1 is an aryl group, each Are is independently a phenyl group or the like, W is a biphenyl group or the like, Z is an ethylene group that is substituted with a phenyl group or the like, and L is a chlorine atom or if Z has a phenyl group or a C 1-3 alkoxyphenyl group, L is one of carbon atoms constituting the phenyl group or the C 1-3 alkoxyphenyl group.

  本发明提供了一种制备由公式（1a），（1b）或（1c）表示的化合物的方法，包括在氢气气氛下，在公式（5）表示的金属配合物，无机碱和溶剂的存在下，还原由公式（3）表示的化合物以获得由公式（4）表示的化合物。在该式中，Ar1是芳基基团，每个Are独立地是苯基或类似的基团，W是联苯基团或类似的基团，Z是被苯基或类似基团取代的乙烯基团，如果Z具有苯基或C1-3烷氧基苯基基团，则L是构成苯基或C1-3烷氧基苯基基团的碳原子之一。
• Cross Metathesis as a General Strategy for the Synthesis of Prostacyclin and Prostaglandin Analogues
  作者：Neil A. Sheddan、Johann Mulzer

  DOI：10.1021/ol061141u

  日期：2006.7.1

  [GRAPHICS]A cross metathesis ( CM) approach has been successfully applied to introduce fully functionalized omega-side chain appendages of various prostacyclin and prostaglandin analogues, resulting in high (E)-selectivities for the C13-C14 double bond and leading to the total syntheses of isocarbacyclin, 15R-TIC, carbacyclin, and PGF(2 alpha) and the formal syntheses of 15-deoxy-TIC and PGJ(2).
• US9828356B2
  申请人：——

  公开号：US9828356B2

  公开（公告）日：2017-11-28
• US9890135B1
  申请人：——

  公开号：US9890135B1

  公开（公告）日：2018-02-13