(1'S,8a'R)-1'-tert-butoxyspiro(cyclopropane-1,8'octahydroindolizin)-7'-one | 186807-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (1'S,8a'R)-1'-tert-butoxyspiro(cyclopropane-1,8'octahydroindolizin)-7'-one
• 英文别名: (1S,8aR)-1-[(2-methylpropan-2-yl)oxy]spiro[1,2,3,5,6,8a-hexahydroindolizine-8,1'-cyclopropane]-7-one
• CAS: 186807-12-5
• 化学式: C₁₄H₂₃NO₂
• 分子量: 237.342
• InChiKey: JWNWLBNGLQDONQ-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'S,8a'R)-1'-tert-butoxyspiro(cyclopropane-1,8'octahydroindolizin)-7'-one 在 三氟乙酸 作用下， 以84%的产率得到(1'S,8a'R)-1'-hydroxyspiro(cyclopropane-1,8'octahydroindolizin)-7'-one
  参考文献：
  名称：

  Versatile Synthetic Approaches Towards Aza-analogues of Illudin and Ptaquilosin Sesquiterpenes

  摘要：

  通过手性吡咯烷硝基与双环亚丙基或亚甲基丙基丙烷的 1,3-二极环加成反应，以及加成物的热重排，合成了具有δ-螺环丙烷基团的吲哚嗪酮类化合物，它们是强致癌倍半萜类化合物哌喹罗苷和伊柳丁的杂环类似骨架。它们在 pUC18 DNA 质粒上具有适度的 DNA 裂解活性，为了解这类化合物的结构-活性关系提供了有用的线索。

  DOI：

  10.1055/s-1997-684
• 作为产物：
  描述：

  (4S)-4-tert-butoxy-3,4-dihydro-2H-pyrrole 1-oxide 以 xylene 、 苯 为溶剂， 反应 56.0h， 生成 (1'S,8a'R)-1'-tert-butoxyspiro(cyclopropane-1,8'octahydroindolizin)-7'-one
  参考文献：
  名称：

  Studies on the Synthesis of Aza Analogues of Illudins by Cycloadditions to Highly Strained Methylenecyclopropanes

  摘要：

  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.

  DOI：

  10.1021/jo990873f

文献信息

• Versatile Synthetic Approaches Towards Aza-analogues of Illudin and Ptaquilosin Sesquiterpenes
  作者：Beatrice Anichini、Andrea Goti、Alberto Brandi、Sergei Kozhushkov、Armin de Meijere

  DOI：10.1055/s-1997-684

  日期：——

  Indolizidinones with a α-spirocyclopropane group, obtained by 1,3-dipolar cycloaddition of chiral pyrroline nitrones to bicyclopropylidene, or methylenespiropentane, and thermal rearrangement of the adducts, have been synthesized as aza-analogous skeleton to the potent carcinogenic sesquiterpenes ptaquiloside and illudin. Their moderate DNA cleaving activity on a pUC18 DNA plasmid furnishes useful hints about structure-activity relationships for this class of compounds.

  通过手性吡咯烷硝基与双环亚丙基或亚甲基丙基丙烷的 1,3-二极环加成反应，以及加成物的热重排，合成了具有δ-螺环丙烷基团的吲哚嗪酮类化合物，它们是强致癌倍半萜类化合物哌喹罗苷和伊柳丁的杂环类似骨架。它们在 pUC18 DNA 质粒上具有适度的 DNA 裂解活性，为了解这类化合物的结构-活性关系提供了有用的线索。
• 3-Spirocyclopropanedihydro- and -tetrahydropyridin-4-ones from Nitrone Cycloadducts of Bicyclopropylidene via 1-(1′-Aminomethylcyclopropyl)cyclopropanol under PdII Catalysis
  作者：Julia Revuelta、Stefano Cicchi、Armin de Meijere、Alberto Brandi

  DOI：10.1002/ejoc.200700912

  日期：2008.2

  A series of 3-spirocyclopropanedihydro- and -tetrahydropyrid-4-ones have been synthesized by nitrone cycloaddition to 1,1′-bicyclopropylidene (BCP), chemoselective reduction of the N–O bond of the isoxazolidine ring, and PdII-catalyzed cascade rearrangement of the β-aminocyclopropanol derivatives into the final products. The new tetrahydropyridone derivatives were also prepared by thermal rearrangement

  通过硝酮环加成到 1,1'-双环亚丙基 (BCP)、异恶唑烷环的 N-O 键的化学选择性还原和 PdII 催化的级联重排合成了一系列 3-螺环丙烷二氢和 -四氢吡啶-4-酮β-氨基环丙醇衍生物转化为最终产品。新的四氢吡啶酮衍生物也是通过异恶唑烷的热重排制备的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• 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.