1-[[3-methoxy-5-(2-methylpropyl)-4-oxido-6-phenylmethoxypyrazin-4-ium-2-yl]methyl]indole | 135074-03-2

• 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: 1-[[3-methoxy-5-(2-methylpropyl)-4-oxido-6-phenylmethoxypyrazin-4-ium-2-yl]methyl]indole
• CAS: 135074-03-2
• 化学式: C₂₅H₂₇N₃O₃
• 分子量: 417.508
• InChiKey: VUKKYKUOCWQSBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-(benzyloxy)-6-(hydroxymethyl)-3-isobutyl-5-methoxypyrazine 4-oxide 在 四丁基碘化铵 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 3.5h， 生成 1-[[3-methoxy-5-(2-methylpropyl)-4-oxido-6-phenylmethoxypyrazin-4-ium-2-yl]methyl]indole
  参考文献：
  名称：

  The first total synthesis of OPC-15161

  摘要：

  The first total synthesis of OPC-15161, a novel inhibitor of superoxide generation by guinea pig macrophages, has been accomplished via a convergent and efficient route exploiting the coupling of the fully functionalized pyrazine part with the indolyl group. 2-(Hydroxyimino)-4-methylpentanoic acid and ethyl aminocyanoacetate were condensed with DCC to afford the amide 3, which was converted to pyrazinone N-oxide 4 via intramolecular cyclization between the oxime and cyano groups. O-Benzylation of 4 followed by reduction of the ethoxycarbonyl group by DIBALH gave the aminopyrazine alcohol 7. The aryl chloride 8 was obtained by the direct substitutive deamination using isoamyl nitrite and copper salts. After protection of the hydroxyl group, the methoxy group was introduced at the 5-position via treatment of 2,5-bis(benzyloxy)pyrazine 4-oxide 10 with methoxide to afford 11. The methoxy compound 11 was converted to benzylic iodide 14 via deprotection, mesylation, and iodination. The functionalized pyrazine skeleton 14 was coupled with the zinc salt of indole to produce 17, which upon catalytic hydrogenolysis afforded OPC-15161.

  DOI：

  10.1021/jo00016a012