7,9-dimethoxy-3,8-dimethylbenzo[g]isoquinoline-5,10-dione | 849667-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 7,9-dimethoxy-3,8-dimethylbenzo[g]isoquinoline-5,10-dione
• CAS: 849667-74-9
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: OXPWHUOXQYHRDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7,9-dimethoxy-3,8-dimethylbenzo[g]isoquinoline-5,10-dione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到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：

  2-acetonyl-5,7-dimethoxy-6-methyl-3-(phenoxymethyl)naphthoquinone 在 air 、 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以72%的产率得到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

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.