allyl {(3aS,5R,5aR,9aS,9bS)-5-[(tert-butyldimethylsilyl)oxy]-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-8-yl} carbonate | 1429033-56-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: allyl {(3aS,5R,5aR,9aS,9bS)-5-[(tert-butyldimethylsilyl)oxy]-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-8-yl} carbonate
• 英文别名: [(3aS,5R,5aR,9aS,9bS)-5-[tert-butyl(dimethyl)silyl]oxy-2,2,5a,9-tetramethyl-4,5,6,7,9a,9b-hexahydro-3aH-naphtho[1,2-d][1,3]dioxol-8-yl] prop-2-enyl carbonate
• CAS: 1429033-56-6
• 化学式: C₂₅H₄₂O₆Si
• 分子量: 466.69
• InChiKey: MVABTUKTSBDSSO-OAIJQJBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  allyl {(E)-4-[(4S,5S)-5-{2-[(tert-butyldimethylsilyl)oxy]-3-methylbut-3-en-1-yl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbuta-1,3-dien-2-yl} carbonate 在 2,6-二叔丁基-4-甲基苯酚 作用下， 以 邻二氯苯 为溶剂， 反应 72.0h， 以27.4%的产率得到allyl {(3aS,5R,5aR,9aS,9bS)-5-[(tert-butyldimethylsilyl)oxy]-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-8-yl} carbonate
  参考文献：
  名称：

  A Stereoconvergent Intramolecular Diels–Alder Cycloaddition Related to the Construction of the Decalin Core of neo-Clerodane Diterpenoids

  摘要：

  Several examples of a highly specific, stereoconvergent intramolecular Diels-Alder cycloaddition that led to the trans-decalin core of neo-clerodane diterpenoids are described. The relative configuration adjacent to the dienophile, which led to C4 of the decalin system, as well as the electron withdrawing effects of various substituents and conformational rigidity of the Diels-Alder precursors were explored.

  DOI：

  10.1021/jo400029u