isagarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异色满醌
• 英文名称: isagarin
• 英文别名: 13-Methyl-14,16-dioxatetracyclo[11.2.1.02,11.04,9]hexadeca-2(11),4,6,8-tetraene-3,10-dione
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: ZKIRNBLLNJPYKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-二甲氧基萘-2-甲醛 在 四氧化锇 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 44.25h， 生成 isagarin
  参考文献：
  名称：

  Synthesis of Isagarin, a New Type of Tetracyclic Naphthoquinone from Pentas longiflora

  摘要：

  Isagarin (1) was synthesized in four steps from 1,4-dimethoxynaphthaldehyde (4). The key intermediate 2-(1,2-dihydroxyethyl)-1,4-naphthoquinon (3) was found to react with acylated pyridinium ylides to afford, after spontaneous intramolecular condensation, the desired natural product isagarin (1). Depending on the type of acylated pyridinium ylides, different types of new pyranonaphthoquinone derivatives were obtained.

  DOI：

  10.1021/jo9813888

文献信息

• Synthesis of Isagarin, a New Type of Tetracyclic Naphthoquinone from <i>Pentas longiflora</i>
  作者：Bart Kesteleyn、Luc Van Puyvelde、Norbert De Kimpe

  DOI：10.1021/jo9813888

  日期：1999.1.1

  Isagarin (1) was synthesized in four steps from 1,4-dimethoxynaphthaldehyde (4). The key intermediate 2-(1,2-dihydroxyethyl)-1,4-naphthoquinon (3) was found to react with acylated pyridinium ylides to afford, after spontaneous intramolecular condensation, the desired natural product isagarin (1). Depending on the type of acylated pyridinium ylides, different types of new pyranonaphthoquinone derivatives were obtained.