methyl (1R,2R,3R,7R,8S,11R)-11-allyl-10-hydroxy-3-isopropyl-6-methyl-12-oxatricyclo[6.3.1.0^2,7]dodeca-5,9-diene-9-carboxylate | 876748-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: methyl (1R,2R,3R,7R,8S,11R)-11-allyl-10-hydroxy-3-isopropyl-6-methyl-12-oxatricyclo[6.3.1.0^2,7]dodeca-5,9-diene-9-carboxylate
• 英文别名: methyl (1R,2R,3R,7R,8S,11R)-10-hydroxy-6-methyl-3-propan-2-yl-11-prop-2-enyl-12-oxatricyclo[6.3.1.02,7]dodeca-5,9-diene-9-carboxylate
• CAS: 876748-93-5
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: QAJJADTYHGYPRO-ODWBRZHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  methyl (1R,2R,3R,7R,8S,11R)-11-allyl-10-hydroxy-3-isopropyl-6-methyl-12-oxatricyclo[6.3.1.0^2,7]dodeca-5,9-diene-9-carboxylate 在 六氯丙酮 、 bis(cyclohexanyl)borane 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 8.83h， 生成 (1R,2R,6R,7R,8R,9R)-9-(3-chloropropyl)-6-isopropyl-3-methyl-12-oxatricyclo[6.3.1.0^2,7]dodec-3-en-10-one
  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：

  丙烯酰碘 、 (1S,2R,3R,7R,8S)-10-Hydroxy-3-isopropyl-6-methyl-12-oxa-tricyclo[6.3.1.0^2,7]dodeca-5,9-diene-9-carboxylic acid methyl ester 在 正丁基锂 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 以90%的产率得到methyl (1R,2R,3R,7R,8S,11R)-11-allyl-10-hydroxy-3-isopropyl-6-methyl-12-oxatricyclo[6.3.1.0^2,7]dodeca-5,9-diene-9-carboxylate
  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