1β-Hydroxy-12β-methoxypicrasane-2,11,16-trione | 139346-55-7

• 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: 1β-Hydroxy-12β-methoxypicrasane-2,11,16-trione
• 英文别名: (1R,2S,3S,6R,7S,9R,13S,14R,15S,17S)-3-hydroxy-15-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadecane-4,11,16-trione
• CAS: 139346-55-7
• 化学式: C₂₁H₃₀O₆
• 分子量: 378.466
• InChiKey: CNVNALWHDVQWTF-QACIEHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1β-Hydroxy-12β-methoxypicrasane-2,11,16-trione 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 反应 16.0h， 以63%的产率得到12β-Methoxy-1β,2β,11β-trihydroxypicrasan-16-one
  参考文献：
  名称：

  A partial synthesis of (-)-shinjulactone H from (+)-quassin

  摘要：

  A partial synthesis of (-)-shinjulactone H (3) from (+)-quassin (1) required the selective manipulation of two similar O-methyldiosphenol groups. Protection of the delta-lactone in 1 as an ortho ester, selective reduction of the C-1 carbonyl group, hydrolysis of the resulting enol ether in the A ring, and catalytic hydrogenation of the O-methyldiosphenol in the C ring delivered an intermediate possessing an alpha-ketol group in the A ring and an alpha-methoxy ketone group in the C ring. Demethylation and concomitant alpha-ketol tautomerization in the A ring delivered (-)-shinjulactone H (3).

  DOI：

  10.1021/jo00034a008
• 作为产物：
  描述：

  2,12-Dimethoxy-2,12-picradiene-1,11,16-trione 16-(ethylene ketal) 在 platinum(IV) oxide sodium tetrahydroborate 、 cerium(III) chloride 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 13.75h， 生成 1β-Hydroxy-12β-methoxypicrasane-2,11,16-trione
  参考文献：
  名称：

  A partial synthesis of (-)-shinjulactone H from (+)-quassin

  摘要：

  A partial synthesis of (-)-shinjulactone H (3) from (+)-quassin (1) required the selective manipulation of two similar O-methyldiosphenol groups. Protection of the delta-lactone in 1 as an ortho ester, selective reduction of the C-1 carbonyl group, hydrolysis of the resulting enol ether in the A ring, and catalytic hydrogenation of the O-methyldiosphenol in the C ring delivered an intermediate possessing an alpha-ketol group in the A ring and an alpha-methoxy ketone group in the C ring. Demethylation and concomitant alpha-ketol tautomerization in the A ring delivered (-)-shinjulactone H (3).

  DOI：

  10.1021/jo00034a008