(2R)-2-methyl-2-[(1E)-4-methylpenta-1,3-dienyl]cyclohexan-1-one | 179749-19-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2-methyl-2-[(1E)-4-methylpenta-1,3-dienyl]cyclohexan-1-one
• CAS: 179749-19-0
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: SNOWOUCAEYZQTH-BCRSCGJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R)-2-methyl-2-[(1E)-4-methylpenta-1,3-dienyl]cyclohexan-1-one 在 碘 、 magnesium 、 lithium diisopropyl amide 作用下， 反应 11.67h， 生成 (1S,2R,6R)-1-[[5-methoxy-2-(methoxymethoxy)phenyl]methyl]-2,6-dimethyl-2-[(1E)-4-methylpenta-1,3-dienyl]cyclohexan-1-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 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 苯基溴化硒 、 双氧水 、 对甲苯磺酸 、 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 5.25h， 生成 (2R)-2-methyl-2-[(1E)-4-methylpenta-1,3-dienyl]cyclohexan-1-one
  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.