(-)-O-ethyl-14-epimelohenine B | 1415841-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (-)-O-ethyl-14-epimelohenine B
• 英文别名: (10S,12S,17S)-10-ethoxy-12-ethyl-9,16-diazapentacyclo[14.2.1.03,8.09,18.012,17]nonadeca-1(18),3,5,7-tetraen-2-one
• CAS: 1415841-67-6
• 化学式: C₂₁H₂₆N₂O₂
• 分子量: 338.45
• InChiKey: ZTFSEQSAIJFNOD-WMQCIHAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  eburnamine 在 四丁基溴化铵 、 氧气 、 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.17h， 生成 (-)-O-ethyl-14-epimelohenine B
  参考文献：
  名称：

  The Synthesis of Melohenine B and a Related Natural Product

  摘要：

  A concise synthesis of melohenine B and O-ethyl-14-epimelohenine B, from eburnamonine, was achieved via a biomimetic diastereoselective singlet oxygen-mediated oxidative cleavage of the indole C2-C7 bond. These studies enabled the assignment of the absolute configuration of the natural products. In line with a proposed biosynthetic pathway, the resulting nine-membered ring containing products could be converted to the corresponding quinolones.

  DOI：

  10.1021/ol302859j

文献信息

• The Synthesis of Melohenine B and a Related Natural Product
  作者：Christopher S. Lancefield、Linna Zhou、Tomas Lébl、Alexandra M. Z. Slawin、Nicholas J. Westwood

  DOI：10.1021/ol302859j

  日期：2012.12.21

  A concise synthesis of melohenine B and O-ethyl-14-epimelohenine B, from eburnamonine, was achieved via a biomimetic diastereoselective singlet oxygen-mediated oxidative cleavage of the indole C2-C7 bond. These studies enabled the assignment of the absolute configuration of the natural products. In line with a proposed biosynthetic pathway, the resulting nine-membered ring containing products could be converted to the corresponding quinolones.