epimeloscine | 24314-58-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 山橙属生物碱
• 英文名称: epimeloscine
• 英文别名: (1R,10R,12S,19S)-12-ethenyl-8,16-diazapentacyclo[10.6.1.01,10.02,7.016,19]nonadeca-2,4,6,13-tetraen-9-one
• CAS: 24314-58-7
• 化学式: C₁₉H₂₀N₂O
• 分子量: 292.381
• InChiKey: BEMFQIDPZLYEBJ-QZHFEQFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  epimeloscine 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 以83%的产率得到meloscine
  参考文献：
  名称：

  Highly functionalized donor–acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids

  摘要：

  A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodious alkaloids. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.016
• 作为产物：
  描述：

  tert-butyl 4-(2-(2,2-divinylcyclopropanecarboxamido)phenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate 在 Hoveyda-Grubbs catalyst second generation 、 偶氮二异丁腈 、 三正丁基氢锡 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 epimeloscine
  参考文献：
  名称：

  Highly functionalized donor–acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids

  摘要：

  A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodious alkaloids. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.016

文献信息

• Highly functionalized donor–acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids
  作者：Alexander F.G. Goldberg、Robert A. Craig、Nicholas R. O’Connor、Brian M. Stoltz

  DOI：10.1016/j.tetlet.2014.09.016

  日期：2015.6

  A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodious alkaloids. (C) 2014 Elsevier Ltd. All rights reserved.