6-phenyl-5-azaspiro[2.5]oct-6-en-8-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-phenyl-5-azaspiro[2.5]oct-6-en-8-one
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: YRDUFYVBYZTOPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲腈 N-氧化物 以 邻二氯苯 、 苯 为溶剂， 反应 30.0h， 生成 6-phenyl-5-azaspiro[2.5]oct-6-en-8-one
  参考文献：
  名称：

  1,3-Dipolar cycloadditions to methylenespiro[2.2]pentane: a complementary access to spiro cyclopropanated azaheterocycles

  摘要：

  氰基氧化物与亚甲基螺[2.2]戊烷的环加成-热重排反应生成5-氮杂螺[2.5]辛-6-烯-8-酮衍生物；使用硝酮的过程补充了使用双(环丙烯)进行合成α-螺环丙烷化的杂环酮的方法。

  DOI：

  10.1039/a606434e

文献信息

• Studies on the Synthesis of Aza Analogues of Illudins by Cycloadditions to Highly Strained Methylenecyclopropanes
  作者：Chiara Zorn、Beatrice Anichini、Andrea Goti、Alberto Brandi、Sergei I. Kozhushkov、Armin de Meijere、Lorenzo Citti

  DOI：10.1021/jo990873f

  日期：1999.10.1

  A series of 3-spirocyclopropane-tetrahydropyrid-4-ones has been synthesized by the method consisting of nitrone cycloaddition to bicyclopropylidene and thermal rearrangement of the adducts. Regioisomeric 5-spirocyclopropanetetrahydropyrid-4-ones and 5-spirocyclopropanedihydropyrid-4 ones were instead obtained by cycloaddition of nitrones and nitrile oxides, respectively, to methylenespiropentane, followed by thermal rearrangement. Methylenedispiro[2.0.2.1]heptane gave, in turn, 5,6-bis(spirocyclopropane)dihydropyrid-4 The new compounds were prepared as simple aza analogues of the cytotoxic natural products illudins and ptaquiloside in order to study their activity in cleaving a DNA plasmid. The activities shown by several of the compounds are moderate, but from a comparative qualitative analysis of the results a useful structure-activity relationship for this new class of compounds could be derived.
• 1,3-Dipolar cycloadditions to methylenespiro[2.2]pentane: a complementary access to spiro cyclopropanated azaheterocycles
  作者：Beatrice Anichini、Andrea Goti、Alberto Brandi、Sergei I. Kozhushkov、Armin de Meijere

  DOI：10.1039/a606434e

  日期：——

  The domino cycloaddition–thermal rearrangement of nitrile oxides and methylenespiro[2.2]pentane gives 5-azaspiro[2.5]oct-6-en-8-one derivatives; with a nitrone the process complements the one using bi(cyclopropylidene) for the synthesis of α-spiro cyclopropanated heterocyclic ketones.

  氰基氧化物与亚甲基螺[2.2]戊烷的环加成-热重排反应生成5-氮杂螺[2.5]辛-6-烯-8-酮衍生物；使用硝酮的过程补充了使用双(环丙烯)进行合成α-螺环丙烷化的杂环酮的方法。