6,7-dimethoxy-3,3-dimethylindan-5-ol | 848922-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6,7-dimethoxy-3,3-dimethylindan-5-ol
• 英文别名: 6,7-Dimethoxy-3,3-dimethyl-1,2-dihydroinden-5-ol
• CAS: 848922-40-7
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: TUUNARYHHDUNHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  345.2±42.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-3,3-dimethylindan-5-ol 在 碘苯二乙酸 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.42h， 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：

  在 1,2-丙二醇 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以772 mg的产率得到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

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.