(1R,2S,3R,6R,7R,8R)-6-isopropyl-3-methyl-9-methylen-13-oxo-15-oxatricyclo[6.6.1.0^2,7]pentadec-3-yl acetate | 876748-88-8

• 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)-6-isopropyl-3-methyl-9-methylen-13-oxo-15-oxatricyclo[6.6.1.0^2,7]pentadec-3-yl acetate
• 英文别名: [(1R,2S,3R,6R,7R,8R)-3-methyl-9-methylidene-13-oxo-6-propan-2-yl-15-oxatricyclo[6.6.1.02,7]pentadecan-3-yl] acetate
• CAS: 876748-88-8
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: BYTSPADSDQZHJA-OWQNAKTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,6R,7R,8R)-6-isopropyl-3-methyl-9-methylen-13-oxo-15-oxatricyclo[6.6.1.0^2,7]pentadec-3-yl acetate 在 mercuric trifluoroacetate 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 [(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：

  (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 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 samarium diiodide 、 伯吉斯试剂 、 六氯丙酮 、 偶氮二异丁腈 、 bis(cyclohexanyl)borane 、 potassium tert-butylate 、 水 、 三正丁基氢锡 、 臭氧 、 三乙胺 、 三苯基膦 、 sodium iodide 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 30.67h， 生成 (1R,2S,3R,6R,7R,8R)-6-isopropyl-3-methyl-9-methylen-13-oxo-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