Riccardiphenol B | 179749-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Riccardiphenol B
• 英文别名: 2-[[(6R)-2,6-dimethyl-6-[(1E)-4-methylpenta-1,3-dienyl]cyclohexen-1-yl]methyl]benzene-1,4-diol
• CAS: 179749-28-1
• 化学式: C₂₁H₂₈O₂
• 分子量: 312.452
• InChiKey: QKLQKCMQTKRVJC-JVNGFTGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Riccardiphenol B 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 6.5h， 生成 (8R,10S)-4,8,12,12-tetramethyl-13-oxatetracyclo[8.7.1.03,8.014,18]octadeca-1(17),3,14(18),15-tetraen-17-ol
  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：

  (R)-(+)-2-(2-甲酯基乙基)-2-甲基环己酮 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 、 氯化亚砜 、 草酰氯 、 苯基溴化硒 、 双氧水 、 碘 、 对甲苯磺酸 、 magnesium 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 为溶剂， 反应 20.08h， 生成 Riccardiphenol B
  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

文献信息

• Total Synthesis and Absolute Configuration of Riccardiphenols A and B, Isolated from the Liverwort <i>Riccardia crassa</i>
  作者：Motoo Tori、Tomonobu Hamaguchi、Kumiko Sagawa、Masakazu Sono、Yoshinori Asakawa

  DOI：10.1021/jo952253u

  日期：1996.1.1

  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.