methyl (1S)-1-(6-methoxy-6-oxohex-4-ynyl)cyclohept-2-ene-1-carboxylate | 1588776-79-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (1S)-1-(6-methoxy-6-oxohex-4-ynyl)cyclohept-2-ene-1-carboxylate
• CAS: 1588776-79-7
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: RMFXLDXLZOHUEJ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1S)-1-(6-methoxy-6-oxohex-4-ynyl)cyclohept-2-ene-1-carboxylate 在 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 作用下， 以 丙酮 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  Expedient Construction of the ABEF Azatetracyclic Ring Systems of Lycoctonine-Type and 7,17-seco-Type C₁₉-Diterpenoid Alkaloids

  摘要：

  A synthetic strategy for the modeling construction of the highly bridged azatetracyclic ABEF ring system of numerous lycoctonine-type C-19-diterpenoid alkaloids bearing a characteristic oxygenated quaternary center at C-7 has been successfully developed. The tetracyclic core was constructed rapidly from a readily prepared 6,7-bicyclic AB ring precursor through a 13-step sequence via an advanced tetracyclic N,O-acetal intermediate, which belong to another core structure of natural 7,17-seco-type alkaloids. The key step involves an SmI2-promoted intramolecular radical coupling reaction of an N,O-acetal with a carbonyl group, mimicking a plausible biogenetic transformation.

  DOI：

  10.1021/ol500726x

文献信息

• Two new entries to the ABF tricyclic ring system of 7,17-seco-type C19-diterpenoid alkaloids via free radical cyclization and [3+2] cycloaddition of nitrile oxide
  作者：Yong-Li Li、Meng-Chen Liu、Yin-Juan Meng、Liang Xu

  DOI：10.1016/j.tet.2016.04.027

  日期：2016.6

  Two new approaches for the construction the ABF ring systems of 7,17-seco-type C19-diterpenoid alkaloids have been successfully developed by using free radical cyclization and intramolecular nitrile oxide cycloaddition, respectively, as the key steps. Both methods would probably provide alternative strategies for the elaboration of AEF-rings in the total synthesis of 7,17-seco-type C19-diterpenoid

  为建造两个新的方法中的7,17-的ABF环系开环型Ç 19种-diterpenoid生物碱已经分别通过使用自由基环化和分子内氧化腈环加成，作为关键步骤被研制成功。这两种方法都可能会提供AEF形环的阐述替代策略中的7,17-全合成开环型Ç 19种基于我们的先前准备的BCD环系统-diterpenoid生物碱。