12β-hydroxypicras-1-en-3-one | 112358-35-7

• 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: 12β-hydroxypicras-1-en-3-one
• CAS: 112358-35-7
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: SJJSCXWZSJZRGX-LABYYNJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  12β-hydroxypicras-1-en-3-one 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 chromium trioxide-pyridine complex 、 氢气 、 双氧水 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 60.0h， 生成 12β-hydroxypicrasan-1-one
  参考文献：
  名称：

  Total synthesis of (.+-.)-amarolide, a quassinoid bitter principle

  摘要：

  The first total synthesis of amarolide (1), a bitter tasting quassinoid having a picrasane skeleton with 10 chiral centers, is described in racemic form. The synthesis of (+/-)-1 was accomplished stereoselectively in 35 steps and 0.5% overall yield from a known tricyclic compound 7. An orthoester Claisen rearrangement and a lead tetraacetate oxidation were utilized as key reactions to prepare hydroxy ketone 14 with a complete picrasane skeleton. This hydroxy ketone was transformed into 1 in 18 steps that included 1,3-carbonyl transposition, introduction of hydroxyl groups at C-2 and C-11 positions, and oxidation of an ether to afford a delta-lactone.

  DOI：

  10.1021/jo00003a039
• 作为产物：
  描述：

  12β-hydroxypicrasan-3-one 在 吡啶 、 苯基氯化硒 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 生成 12β-hydroxypicras-1-en-3-one
  参考文献：
  名称：

  Total synthesis of (.+-.)-amarolide, a quassinoid bitter principle

  摘要：

  The first total synthesis of amarolide (1), a bitter tasting quassinoid having a picrasane skeleton with 10 chiral centers, is described in racemic form. The synthesis of (+/-)-1 was accomplished stereoselectively in 35 steps and 0.5% overall yield from a known tricyclic compound 7. An orthoester Claisen rearrangement and a lead tetraacetate oxidation were utilized as key reactions to prepare hydroxy ketone 14 with a complete picrasane skeleton. This hydroxy ketone was transformed into 1 in 18 steps that included 1,3-carbonyl transposition, introduction of hydroxyl groups at C-2 and C-11 positions, and oxidation of an ether to afford a delta-lactone.

  DOI：

  10.1021/jo00003a039