8-hydroxy-6-methoxy-7-methyl-2-(phenoxymethyl)-naphthoquinone | 849667-75-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-hydroxy-6-methoxy-7-methyl-2-(phenoxymethyl)-naphthoquinone
• 英文别名: 8-Hydroxy-6-methoxy-7-methyl-2-(phenoxymethyl)naphthalene-1,4-dione
• CAS: 849667-75-0
• 化学式: C₁₉H₁₆O₅
• 分子量: 324.333
• InChiKey: SDTJZYIYIDLZQR-UHFFFAOYSA-N

物化性质

• 沸点：
  568.5±50.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-hydroxy-6-methoxy-7-methyl-2-(phenoxymethyl)-naphthoquinone 在 air 、 氨 、 三乙胺 、 silver(l) oxide 作用下， 以 乙醇 、 氯仿 、 水 、 乙腈 为溶剂， 反应 10.0h， 生成 7,9-dimethoxy-3,8-dimethylbenzo[g]isoquinoline-5,10-dione
  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：

  [(1Z)-1,3-dimethoxy-2-methylbuta-1,3-dienoxy]-trimethylsilane 、 2-bromo-6-(phenoxymethyl)benzo-1,4-quinone 在 silica gel 作用下， 以 甲苯 为溶剂， 以55%的产率得到8-hydroxy-6-methoxy-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.