2,5,6-trihydroxy-1-(indol-3-yl)hexa-1E-en-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,5,6-trihydroxy-1-(indol-3-yl)hexa-1E-en-3-one
• 英文别名: (E)-2,5,6-trihydroxy-1-(1H-indol-3-yl)hex-1-en-3-one
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: GNGVXPNHDFBYPH-WLRTZDKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  93.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-C-(indol-3-yl)methyl-α-L-xylo-hex-3-ulofuranosonic acid 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 1-deoxy-1-(indol-3-yl)-α-L-sorbopyranose 、 1-deoxy-1-(indol-3-yl)-α-L-tagatopyranose 、 2-hydroxy-4-hydroxymethyl-5-(indol-3-yl)cyclopent-2-enone 、 2,5,6-trihydroxy-1-(indol-3-yl)hexa-1E-en-3-one
  参考文献：
  名称：

  摘要：

  Transformation of ascorbigen in an acidic medium, which affects the carbohydrate moiety of the molecule and results in the formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone, 5-hydroxymethyl-2-(indol-3-yl)methylidenetetrahydrofuran-3-one, and 2-(indol-3-yl)acetylfuran, was investigated. Isolation and identification of the intermediates allowed the elucidation of the mechanism of this domino-type reaction.

  DOI：

  10.1023/a:1014087630107

文献信息

• ——
  作者：L. N. Lysenkova、M. I. Reznikova、A. M. Korolev、M. N. Preobrazhenskaya

  DOI：10.1023/a:1014087630107

  日期：——

  Transformation of ascorbigen in an acidic medium, which affects the carbohydrate moiety of the molecule and results in the formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone, 5-hydroxymethyl-2-(indol-3-yl)methylidenetetrahydrofuran-3-one, and 2-(indol-3-yl)acetylfuran, was investigated. Isolation and identification of the intermediates allowed the elucidation of the mechanism of this domino-type reaction.