3-Methoxy-6-(phenylmethoxymethyl)cyclohex-2-en-1-one | 171624-96-7

• 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: 3-Methoxy-6-(phenylmethoxymethyl)cyclohex-2-en-1-one
• CAS: 171624-96-7
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: KEGRWZNFWCZFBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methoxy-6-(phenylmethoxymethyl)cyclohex-2-en-1-one 在 palladium on activated charcoal 氢气 、 二异丁基氢化铝 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 异丙醇 为溶剂， 反应 4.0h， 生成 4-(苄氧基甲基)环己酮
  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：

  3-甲氧基-2-环己烯-1-酮 、 苄基氯甲基醚 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到3-Methoxy-6-(phenylmethoxymethyl)cyclohex-2-en-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

文献信息

• Tremorgenic Indole Alkaloids. 9. Asymmetric construction of an Advanced F-G-H-ring Lactone precursor for the Synthesis of Penitrem D
  作者：Amos B. Smith、Ernest G. Nolen、Ryuichi Shirai、Frances R. Blase、Mitsuaki Ohta、Noritaka Chida、Richard A. Hartz、Duke M. Fitch、William M. Clark、Paul A. Sprengeler

  DOI：10.1021/jo00129a025

  日期：1995.12

  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.