6,8-dimethoxy-7-methyl-2-(phenoxymethyl)-naphthoquinone | 849667-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,8-dimethoxy-7-methyl-2-(phenoxymethyl)-naphthoquinone
• 英文别名: 6,8-Dimethoxy-7-methyl-2-(phenoxymethyl)naphthalene-1,4-dione
• CAS: 849667-76-1
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: INHKLTUKPAMWGW-UHFFFAOYSA-N

物化性质

• 沸点：
  544.0±50.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,8-dimethoxy-7-methyl-2-(phenoxymethyl)-naphthoquinone 在 air 、 氨 、 三溴化硼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 7.5h， 生成 6-deoxy-8-methylbostrycoidin
  参考文献：
  名称：

  Total synthesis of four naturally occurring 2-azaanthraquinone antibiotics, 6-deoxy-8-methylbostrycoidin, 6-deoxybostrycoidin, 7-O-demethyl-6-deoxybostrycoidin and scorpinone

  摘要：

  A total synthesis of four natural 2-azaanthraquinones, 6-deoxy-8-methylbostrycoidin, 6-deoxybostrycoidin, 7-0-demethyl-6-deoxybostrycoidin and scorpinone was accomplished using an optimized procedure for 2-azaanthraquinone synthesis, involving a [4+2]-cycloaddition protocol, of a polyoxygenated diene with a suitably functionalized benzoquinone, acetonylation with pyridinium ylids, cyclisation with ammonia and O-demethylation with boron(III) bromide. 2-Azaanthraquinones are rarely found in nature and reveal interesting physiological properties. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.035
• 作为产物：
  描述：

  碘甲烷 、 8-hydroxy-6-methoxy-7-methyl-2-(phenoxymethyl)-naphthoquinone 在 silver(l) oxide 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以93%的产率得到6,8-dimethoxy-7-methyl-2-(phenoxymethyl)-naphthoquinone
  参考文献：
  名称：

  Total synthesis of four naturally occurring 2-azaanthraquinone antibiotics, 6-deoxy-8-methylbostrycoidin, 6-deoxybostrycoidin, 7-O-demethyl-6-deoxybostrycoidin and scorpinone

  摘要：

  A total synthesis of four natural 2-azaanthraquinones, 6-deoxy-8-methylbostrycoidin, 6-deoxybostrycoidin, 7-0-demethyl-6-deoxybostrycoidin and scorpinone was accomplished using an optimized procedure for 2-azaanthraquinone synthesis, involving a [4+2]-cycloaddition protocol, of a polyoxygenated diene with a suitably functionalized benzoquinone, acetonylation with pyridinium ylids, cyclisation with ammonia and O-demethylation with boron(III) bromide. 2-Azaanthraquinones are rarely found in nature and reveal interesting physiological properties. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.035

文献信息

• Total synthesis of four naturally occurring 2-azaanthraquinone antibiotics, 6-deoxy-8-methylbostrycoidin, 6-deoxybostrycoidin, 7-O-demethyl-6-deoxybostrycoidin and scorpinone
  作者：Tuyen Nguyen Van、Guido Verniest、Sven Claessens、Norbert De Kimpe

  DOI：10.1016/j.tet.2005.01.035

  日期：2005.2

  A total synthesis of four natural 2-azaanthraquinones, 6-deoxy-8-methylbostrycoidin, 6-deoxybostrycoidin, 7-0-demethyl-6-deoxybostrycoidin and scorpinone was accomplished using an optimized procedure for 2-azaanthraquinone synthesis, involving a [4+2]-cycloaddition protocol, of a polyoxygenated diene with a suitably functionalized benzoquinone, acetonylation with pyridinium ylids, cyclisation with ammonia and O-demethylation with boron(III) bromide. 2-Azaanthraquinones are rarely found in nature and reveal interesting physiological properties. (C) 2005 Elsevier Ltd. All rights reserved.