2-[[(1R,2R,6S)-1-hydroxy-2,6-dimethyl-2-[(1E)-4-methylpenta-1,3-dienyl]cyclohexyl]methyl]benzene-1,4-diol | 179749-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[[(1R,2R,6S)-1-hydroxy-2,6-dimethyl-2-[(1E)-4-methylpenta-1,3-dienyl]cyclohexyl]methyl]benzene-1,4-diol
• CAS: 179749-23-6
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: JBTCYNPKTNKCKX-JMNLPZGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[[(1R,2R,6S)-1-hydroxy-2,6-dimethyl-2-[(1E)-4-methylpenta-1,3-dienyl]cyclohexyl]methyl]benzene-1,4-diol 在 吡啶 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 4.5h， 生成 [(4S,4aR,12aR)-4a-acetyloxy-4,12a-dimethyl-11-(2-methylprop-1-enyl)-2,3,4,5,11,12-hexahydro-1H-benzo[d][1]benzoxocin-7-yl] acetate
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Riccardiphenols A and B, Isolated from the Liverwort Riccardia crassa

  摘要：

  The title compounds were synthesized as optically active forms using chiral Michael addition of the imine, prepared from 2-methylcyclohexanone and (S)-(-)-phenylethylamine, to methyl propiolate. The etherification of the intermediate triol was accomplished by TsOH-catalyzed cyclization. The absolute configurations of the natural products, riccardiphenols A and B, were established as 1 and 2, respectively.

  DOI：

  10.1021/jo952253u
• 作为产物：
  描述：

  3-{(R)-1-Methyl-2-[(E)-(S)-1-phenyl-ethylimino]-cyclohexyl}-propionic acid methyl ester 在 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 苯基溴化硒 、 双氧水 、 对甲苯磺酸 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 反应 15.25h， 生成 2-[[(1R,2R,6S)-1-hydroxy-2,6-dimethyl-2-[(1E)-4-methylpenta-1,3-dienyl]cyclohexyl]methyl]benzene-1,4-diol
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Riccardiphenols A and B, Isolated from the Liverwort Riccardia crassa

  摘要：

  The title compounds were synthesized as optically active forms using chiral Michael addition of the imine, prepared from 2-methylcyclohexanone and (S)-(-)-phenylethylamine, to methyl propiolate. The etherification of the intermediate triol was accomplished by TsOH-catalyzed cyclization. The absolute configurations of the natural products, riccardiphenols A and B, were established as 1 and 2, respectively.

  DOI：

  10.1021/jo952253u