(+)-melohenine B | 1415983-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (+)-melohenine B
• 英文别名: (-)-melohenine B；melodinine B；melohenine B；(15S,17R,19S)-15-ethyl-17-hydroxy-1,11-diazatetracyclo[9.6.2.02,7.015,19]nonadeca-2,4,6-triene-8,18-dione
• CAS: 1415983-10-6
• 化学式: C₁₉H₂₄N₂O₃
• 分子量: 328.411
• InChiKey: QUTCWFPVUVMVTM-LMMKCTJWSA-N

物化性质

• 沸点：
  534.6±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-melohenine B 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (10R,12S,17S)-12-ethyl-10-hydroxy-9,16-diazapentacyclo[14.2.1.03,8.09,18.012,17]nonadeca-1(18),3,5,7-tetraen-2-one 、
  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
• 作为产物：
  描述：

  长春布宁 在 lithium aluminium tetrahydride 、 亚甲基蓝 、 氧气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (+)-melohenine 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.