(1R,2S,3R,6R,7R,8R,13R)-13-hydroxy-6-isopropyl-3,13-dimethyl-9-methylen-15-oxatricyclo[6.6.1.0^2,7]pentadec-3-yl acetate | 876748-89-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,3R,6R,7R,8R,13R)-13-hydroxy-6-isopropyl-3,13-dimethyl-9-methylen-15-oxatricyclo[6.6.1.0^2,7]pentadec-3-yl acetate
• 英文别名: [(1R,2S,3R,6R,7R,8R,13R)-13-hydroxy-3,13-dimethyl-9-methylidene-6-propan-2-yl-15-oxatricyclo[6.6.1.02,7]pentadecan-3-yl] acetate
• CAS: 876748-89-9
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: KTVYAKMPBDLPRM-RAKJYYOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,6R,7R,8R,13R)-13-hydroxy-6-isopropyl-3,13-dimethyl-9-methylen-15-oxatricyclo[6.6.1.0^2,7]pentadec-3-yl acetate 在 mercuric trifluoroacetate 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以60%的产率得到[(1R,2S,6R,8R,9S,10R,13R,14R)-2,6,10-trimethyl-13-propan-2-yl-15,16-dioxatetracyclo[6.6.1.12,6.09,14]hexadecan-10-yl] acetate
  参考文献：
  名称：

  A General Route toward the Synthesis of the Cladiellin Skeleton Utilizing a SmI₂-Mediated Cyclization

  摘要：

  [graphics]An efficient synthesis of the cladiellin skeleton is reported utilizing methods that were previously developed in this laboratory. The approach is based on a SmI2-mediated cyclization reaction for the construction of the oxacyclononane unit. A [4 + 3] annulation strategy was used to create the octahydroisobenzofuran moiety. This route provides the cladiellin skeleton in only 14 steps without the use of protecting groups. The present approach also enabled the synthesis of the 3,7-diastereomer of the natural product polyanthellin A.

  DOI：

  10.1021/jo052290d
• 作为产物：
  描述：

  (1R,2R,3S,6R,7R,8R,9R)-9-(3-chloropropyl)-6-isopropyl-3-methyl-10-oxo-12-oxatricyclo[6.3.1.0^2,7]dodec-3-yl acetate 在 六甲基磷酰三胺 、 samarium diiodide 、 伯吉斯试剂 、 potassium tert-butylate 、 臭氧 、 sodium iodide 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 16.17h， 生成 (1R,2S,3R,6R,7R,8R,13R)-13-hydroxy-6-isopropyl-3,13-dimethyl-9-methylen-15-oxatricyclo[6.6.1.0^2,7]pentadec-3-yl acetate
  参考文献：
  名称：

  A General Route toward the Synthesis of the Cladiellin Skeleton Utilizing a SmI₂-Mediated Cyclization

  摘要：

  [graphics]An efficient synthesis of the cladiellin skeleton is reported utilizing methods that were previously developed in this laboratory. The approach is based on a SmI2-mediated cyclization reaction for the construction of the oxacyclononane unit. A [4 + 3] annulation strategy was used to create the octahydroisobenzofuran moiety. This route provides the cladiellin skeleton in only 14 steps without the use of protecting groups. The present approach also enabled the synthesis of the 3,7-diastereomer of the natural product polyanthellin A.

  DOI：

  10.1021/jo052290d