2-methoxy-6-(4-methylpent-3-en-1-yl)-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methoxy-6-(4-methylpent-3-en-1-yl)-1,4-naphthoquinone
• 英文别名: 2-Methoxy-6-(4-methylpent-3-enyl)naphthalene-1,4-dione；2-methoxy-6-(4-methylpent-3-enyl)naphthalene-1,4-dione
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: MWMHDNZNMIGFLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(3,7-dimethylocta-2,6-dienyl)-6-methoxybenzene-1,4-diol 在 吡啶 、 氧气 、 copper(l) chloride 作用下， 反应 0.5h， 以24%的产率得到2-methoxy-6-(3',7'-dimethylocta-2',6'-dienyl)[1,4]benzoquinone
  参考文献：
  名称：

  Bio-inspired dimerisation of prenylated quinones directed towards the synthesis of the meroterpenoid natural products, the scabellones

  摘要：

  Stirring 2-geranyl-6-methoxy-1,4-hydroquinone in pyridine/O-2 or 2-gerany1-6-methoxy-1,4-benzoquinone in pyridine/N-2 affords the dimeric meroterpenoid natural products, scabellones A-C in modest to low yields and also identifies 2-methoxy-6-(4-methylpent-3-en-1-yl)-1,4-naPhthoquinone (scabellone E) as a new natural product. The corresponding reaction of the des-methoxy analogue, 2-geranyl-1,4-benzoquinone in degassed pyridine for three days afforded the natural product cordiachromene A (15% yield) and 6-(4-methylpent-3-en-1-yl)-1,4-naphthoquinone (12%), the latter being a likely biosynthetic precursor to the marine meroterpenoid alkaloids, conicaquinones A and B. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.02.024