(3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-vinylhexahydro-2H-cyclopenta[b]furan-2-one | 906000-82-6

• 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-(tert-butyldimethylsilyloxy)-4-vinylhexahydro-2H-cyclopenta[b]furan-2-one
• 英文别名: (3aR,4R,5R,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-4-ethenyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS: 906000-82-6
• 化学式: C₁₅H₂₆O₃Si
• 分子量: 282.455
• InChiKey: FYGJMHPHXZLLJS-FVCCEPFGSA-N

物化性质

• 沸点：
  342.4±42.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-vinylhexahydro-2H-cyclopenta[b]furan-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 盐酸 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 地诺前列素
  参考文献：
  名称：

  Cross Metathesis as a General Strategy for the Synthesis of Prostacyclin and Prostaglandin Analogues

  摘要：

  [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).

  DOI：

  10.1021/ol061141u
• 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 咪唑 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-vinylhexahydro-2H-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

• 一种卡前列素氨丁三醇及其中间体的制备方法
  申请人：广州楷石医药有限公司

  公开号：CN115160202A

  公开（公告）日：2022-10-11

  本发明提供了一种卡前列素氨丁三醇及其中间体的制备方法，所述方法以科里内酯为原料，经过氧化、烯烃偶联化反应、烯烃复分解反应、还原、脱保护、接侧链反应等步骤得到卡前列素氨丁三醇。本发明的方法改善了中间体的制备过程，所述方法操作简便、生产成本低、产率较高、适合工业化生产。
• Iridium-Catalyzed Enantioselective Fluorination of Racemic, Secondary Allylic Trichloroacetimidates
  作者：Qi Zhang、David P. Stockdale、Jason C. Mixdorf、Joseph J. Topczewski、Hien M. Nguyen

  DOI：10.1021/jacs.5b07492

  日期：2015.9.23

  The Ir-catalyzed enantioselective fluorination of racemic, branched allylic trichloroacetiinidates with Et3N center dot 3HF is a mild and efficient route for selective incorporation of fluoride ion into allylic systems. We herein describe the asymmetric fluorination of racemic, secondary allylic electrophiles with Et3N center dot 3HF using a chiral-diene-ligated Ir complex. The methodology enables the formation of acyclic fluorine-containing compounds in good yields with excellent levels of asymmetric induction and overcomes the limitations previously associated with the eiiantioselective construction of secondary allylic fluorides bearing alpha-linear substituents.
• Effect of allylic and homoallylic substituents on cross metathesis: syntheses of prostaglandins F2α and J2
  作者：Neil A. Sheddan、Vladimir B. Arion、Johann Mulzer

  DOI：10.1016/j.tetlet.2006.06.140

  日期：2006.9

  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.
• 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).