cappariloside A | 229483-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cappariloside A
• 英文别名: 2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-indol-3-yl]acetonitrile
• CAS: 229483-41-4
• 化学式: C₁₆H₁₈N₂O₆
• 分子量: 334.329
• InChiKey: ZVFUTZQNUQUJLW-YMILTQATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  139
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 cappariloside A 在 吡啶 作用下， 生成 4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)indole-3-acetonitrile
  参考文献：
  名称：

  1H-Indole-3 acetonitrile glycosides from Capparis spinosa fruits

  摘要：

  Two new glucose-containing 1H-indole-3-acetonitrile compounds, capparilosides A and B, were isolated from mature fruits of Capparis spinosa. On the basis of spectral and chemical evidence, they were shown to be 1H-indole-3-acetonitrile 4-O-beta-glucopyranoside and 1H-indole-3-acetonitrile 4-O-beta-(6'-O-beta-glucopyranosyl)-glucopyranoside respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00669-4
• 作为产物：
  描述：

  4-苄氧基吲哚-3-乙腈 在 palladium on activated charcoal lithium hydroxide 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.5h， 生成 cappariloside A
  参考文献：
  名称：

  The First and Simple Total Synthesis of Cappariloside A

  摘要：

  A lithium hydroxide promoted simple glycosylation of 4-hydroxyindole-3-acetonitrile with 2,3,4, 6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide was developed. Utilizing the method, the first and five steps total synthesis of cappariloside A was achieved from indole-3-carbaldehyde in 41% overall yield.

  DOI：

  10.3987/com-00-8908

文献信息

• The First and Simple Total Synthesis of Cappariloside A
  作者：Masanori Somei、Fumio Yamada

  DOI：10.3987/com-00-8908

  日期：——

  A lithium hydroxide promoted simple glycosylation of 4-hydroxyindole-3-acetonitrile with 2,3,4, 6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide was developed. Utilizing the method, the first and five steps total synthesis of cappariloside A was achieved from indole-3-carbaldehyde in 41% overall yield.
• 1H-Indole-3 acetonitrile glycosides from Capparis spinosa fruits
  作者：İhsan Çaliş、Ayşe Kuruüzüm、Peter Rüedi

  DOI：10.1016/s0031-9422(98)00669-4

  日期：1999.4

  Two new glucose-containing 1H-indole-3-acetonitrile compounds, capparilosides A and B, were isolated from mature fruits of Capparis spinosa. On the basis of spectral and chemical evidence, they were shown to be 1H-indole-3-acetonitrile 4-O-beta-glucopyranoside and 1H-indole-3-acetonitrile 4-O-beta-(6'-O-beta-glucopyranosyl)-glucopyranoside respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.