2-methyl-4-(2,3,4-trimethoxyphenyl)butan-2-ol | 848922-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-methyl-4-(2,3,4-trimethoxyphenyl)butan-2-ol
• CAS: 848922-44-1
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: DAIWMQJCYJTUIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-4-(2,3,4-trimethoxyphenyl)butan-2-ol 在 1,2-丙二醇 、 硫酸 、 三溴化硼 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.67h， 生成 6,7-dimethoxy-3,3-dimethylindan-5-ol
  参考文献：
  名称：

  Synthesis of the Core Structure of Acutumine

  摘要：

  The tricyclic core of the bioactive natural product acutumine has been synthesized. Key steps include an oxidative phenolic coupling to form a masked o-benzoquinone, an anionic oxy-Cope rearrangement to construct an all-carbon quaternary center, and a Michael-type cyclization to form an amine-bearing quaternary carbon. The target compound exists in solution as an enol, in contrast to related compounds that are ketones. A model explaining these observations is presented.

  DOI：

  10.1021/ol050020b
• 作为产物：
  描述：

  (E)-3-(2,3,4-trimethoxy-phenyl)-acrylic acid methyl ester 在 palladium on activated charcoal 氢气 、 碘 、 magnesium 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 18.83h， 生成 2-methyl-4-(2,3,4-trimethoxyphenyl)butan-2-ol
  参考文献：
  名称：

  Synthesis of the Core Structure of Acutumine

  摘要：

  The tricyclic core of the bioactive natural product acutumine has been synthesized. Key steps include an oxidative phenolic coupling to form a masked o-benzoquinone, an anionic oxy-Cope rearrangement to construct an all-carbon quaternary center, and a Michael-type cyclization to form an amine-bearing quaternary carbon. The target compound exists in solution as an enol, in contrast to related compounds that are ketones. A model explaining these observations is presented.

  DOI：

  10.1021/ol050020b

文献信息

• Synthesis of the Core Structure of Acutumine
  作者：Matthew D. Reeder、G. S. C. Srikanth、Spencer B. Jones、Steven L. Castle

  DOI：10.1021/ol050020b

  日期：2005.3.1

  The tricyclic core of the bioactive natural product acutumine has been synthesized. Key steps include an oxidative phenolic coupling to form a masked o-benzoquinone, an anionic oxy-Cope rearrangement to construct an all-carbon quaternary center, and a Michael-type cyclization to form an amine-bearing quaternary carbon. The target compound exists in solution as an enol, in contrast to related compounds that are ketones. A model explaining these observations is presented.