1,8-dihydroxy-6-methoxy-2-methoxycarbonyl-3-methyl-9,10-anthraquinone | 38907-43-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-dihydroxy-6-methoxy-2-methoxycarbonyl-3-methyl-9,10-anthraquinone
• 英文别名: Endocrocin-methylester-6-methylether；Cinnaluteinmethylester；Methyl 1,8-dihydroxy-6-methoxy-3-methyl-9,10-dioxoanthracene-2-carboxylate；methyl 1,8-dihydroxy-6-methoxy-3-methyl-9,10-dioxoanthracene-2-carboxylate
• CAS: 38907-43-6
• 化学式: C₁₈H₁₄O₇
• 分子量: 342.305
• InChiKey: WDBPHVXOFDKHKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,8-dihydroxy-6-methoxy-2-methoxycarbonyl-3-methyl-9,10-anthraquinone 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以98%的产率得到cinnalutein
  参考文献：
  名称：

  An integrated approach to the synthesis of contiguously substituted xanthopurpurins, pachybasins and purpurins.

  摘要：

  Alkylation, hydroxyalkylation and acylation of 3-methyl-, 3-methoxy- and 3,4-dimethoxycrotonates can be induced to occur exclusively in the alpha-Position. Conversion of the products to dienes then provides, through cycloaddition, a wide variety of substitution patterns. This approach is illustrated by simplified syntheses of a number of naturally occurring quinones and confirms the structures proposed for vismiaquinone C, 7-geranylemodin, cinnalutein, 4,5-dihydroxydigitolutein, 2-hydroxyislandicin 1-methyl ether and calyculatone 1-methyl ether.

  DOI：

  10.1016/s0040-4020(01)80322-7
• 作为产物：
  描述：

  3-氯-5-羟基-7-甲氧基萘醌 、 1-methoxy-2-methoxycarbonyl-3-methyl-1-trimethylsiloxy-1,3-butadiene 在 盐酸 作用下， 生成 1,8-dihydroxy-6-methoxy-2-methoxycarbonyl-3-methyl-9,10-anthraquinone
  参考文献：
  名称：

  An integrated approach to the synthesis of contiguously substituted xanthopurpurins, pachybasins and purpurins.

  摘要：

  Alkylation, hydroxyalkylation and acylation of 3-methyl-, 3-methoxy- and 3,4-dimethoxycrotonates can be induced to occur exclusively in the alpha-Position. Conversion of the products to dienes then provides, through cycloaddition, a wide variety of substitution patterns. This approach is illustrated by simplified syntheses of a number of naturally occurring quinones and confirms the structures proposed for vismiaquinone C, 7-geranylemodin, cinnalutein, 4,5-dihydroxydigitolutein, 2-hydroxyislandicin 1-methyl ether and calyculatone 1-methyl ether.

  DOI：

  10.1016/s0040-4020(01)80322-7