6,6,7-trimethoxy-3,3-dimethyl-1,2,3,6-tetrahydroinden-5-one | 848922-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6,7-trimethoxy-3,3-dimethyl-1,2,3,6-tetrahydroinden-5-one
• 英文别名: 6,6,7-Trimethoxy-3,3-dimethyl-1,2-dihydroinden-5-one
• CAS: 848922-39-4
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: ONDLAFVGSONYSB-UHFFFAOYSA-N

物化性质

• 沸点：
  398.8±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,6,7-trimethoxy-3,3-dimethyl-1,2,3,6-tetrahydroinden-5-one 、 烯丙基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.25h， 生成 5-allyl-6,6,7-trimethoxy-3,3-dimethyl-2,3,5,6-tetrahydro-1H-inden-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 1,2-丙二醇 、 碘苯二乙酸 、 硫酸 、 氢气 、 碘 、 三溴化硼 、 potassium hydrogencarbonate 、 对甲苯磺酸 、 magnesium 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 33.67h， 生成 6,6,7-trimethoxy-3,3-dimethyl-1,2,3,6-tetrahydroinden-5-one
  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.