(+/-)-4-<(Benzyloxy)methyl>-3-methyl-2-cyclohexen-1-one | 171624-95-6

• 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: (+/-)-4-<(Benzyloxy)methyl>-3-methyl-2-cyclohexen-1-one
• 英文别名: 3-methyl-4-(phenylmethoxymethyl)cyclohex-2-en-1-one
• CAS: 171624-95-6
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: RTARLOVOQHNUAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-4-<(Benzyloxy)methyl>-3-methyl-2-cyclohexen-1-one 在 copper(l) iodide 18-冠醚-6 、 四甲基乙二胺 、 甲基锂 、 potassium hydride 、 magnesium 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 10.66h， 生成
  参考文献：
  名称：

  Tremorgenic Indole Alkaloids. 9. Asymmetric construction of an Advanced F-G-H-ring Lactone precursor for the Synthesis of Penitrem D

  摘要：

  Lactone (+)-12 is envisioned as the precursor to the F-G-H rings of penitrem D (4) in our ongoing synthetic venture. The efficient, stereocontrolled introduction of the vicinal quaternary methyl groups present the major challenge in the construction of this subunit. Our first route to (+/-)-12 was marked by low overall yield (<2%) and the instability of several key intermediates; these deficiencies were rectified in a second-generation approach that produced optically active material (18 steps from 19a, 2.1% overall). The successful strategies exploited enolate generation via either conjugate additions to alpha,beta-enones or the Evans oxy-Cope rearrangement as key regiochemical control elements.

  DOI：

  10.1021/jo00129a025
• 作为产物：
  描述：

  苄基氯甲基醚 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.75h， 生成 (+/-)-4-<(Benzyloxy)methyl>-3-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  Tremorgenic Indole Alkaloids. 9. Asymmetric construction of an Advanced F-G-H-ring Lactone precursor for the Synthesis of Penitrem D

  摘要：

  Lactone (+)-12 is envisioned as the precursor to the F-G-H rings of penitrem D (4) in our ongoing synthetic venture. The efficient, stereocontrolled introduction of the vicinal quaternary methyl groups present the major challenge in the construction of this subunit. Our first route to (+/-)-12 was marked by low overall yield (<2%) and the instability of several key intermediates; these deficiencies were rectified in a second-generation approach that produced optically active material (18 steps from 19a, 2.1% overall). The successful strategies exploited enolate generation via either conjugate additions to alpha,beta-enones or the Evans oxy-Cope rearrangement as key regiochemical control elements.

  DOI：

  10.1021/jo00129a025