8-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one | 126036-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 8-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one
• 英文别名: 8-Methyl-1-oxaspiro[4.5]deca-3,7-dien-2-one
• CAS: 126036-64-4
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: VDNKBGBKFBTIEM-UHFFFAOYSA-N

物化性质

• 沸点：
  324.5±41.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one 在 palladium on activated charcoal 锂硼氢 、 氢气 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、202.65 kPa 条件下， 反应 36.0h， 生成 4-methyl-1-(3-hydroxypropyl)-cyclohexanol
  参考文献：
  名称：

  General synthesis of 1-oxaspiro[4.5]decan-2-ones and 1-oxaspiro[4.5]decanes from 5-methylene-2(5H)-furanone

  摘要：

  5-Methylene-2(5H)-furanone underwent Diels-Alder cycloadditions to butadiene and several acyclic and cyclic C-substituted dienes, respectively, affording bicyclic and tricyclic spiroadducts in good yields. These compounds are precursors of other unsaturated and saturated spirolactones and also spiroethers, which were obtained through simple chemical reactions, i.e., hydrogenation of C-C double bonds, reduction of the carbonyl group, and Michael addition. The synthesis of 32 spirolactones and eight spiroethers illustrates the scope and efficiency of this method. Many of these products are suitable for use as components of perfumes and aromas owing to their olfactive properties.

  DOI：

  10.1021/jo00019a019
• 作为产物：
  描述：

  4-甲基-3-环己烯-1-酮 在 ammonium cerium(IV) nitrate 、 pentacarbonyl(tetrahydrofuran)chromium(0) 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 19.17h， 生成 8-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one
  参考文献：
  名称：

  过渡金属促进的乙炔异构化反应：-在合成（+/-）-和内酯内酯中的应用

  摘要：

  铬促进的乙炔-亚乙烯基重排已被用于（+/-）-和内酯内酯的合成中。

  DOI：

  10.1016/s0040-4039(00)78524-8

文献信息

• New Synthetic Entries to (±)-Andirolactone
  作者：Marta Planas、Cristobal Segura、Montserrat Ventura、Rosa M. OrtuñTo

  DOI：10.1080/00397919408012641

  日期：1994.3

  Abstract Two new and easy syntheses of (±)-andirolactone are reported, starting from the major Diels-Alder regio-adduct of 5-methylene-2(5H)-furanone and isoprene.

  摘要 从 5-亚甲基-2(5H)-呋喃酮和异戊二烯的主要 Diels-Alder 区域加合物开始，报道了 (±)-andirolactone 的两种新的和简单的合成。
• 5-Methylene-2(5H)-furanone as a dienophile in Diels-Alder cycloadditions: site-selectivity and regioselectivity
  作者：Daniel Alonso、Juan Orti、Vicenc Branchadell、Antonio Oliva、Rosa M. Ortuno、Juan Bertran、Josep Font

  DOI：10.1021/jo00297a021

  日期：1990.5
• ALONSO, DANIEL;ORTI, JUAN;BRANCHADELL, VICENC;OLIVA, ANTONIO;ORTUNO, ROSA+, J. ORG. CHEM., 55,(1990) N0, C. 3060-3063
  作者：ALONSO, DANIEL、ORTI, JUAN、BRANCHADELL, VICENC、OLIVA, ANTONIO、ORTUNO, ROSA+

  DOI：——

  日期：——
• Transition metal promoted acetylene isomerisation reactions:- Application to the synthesis of (+/-)-andirolactone
  作者：Peter Quayle、E.Lucy M. Ward、Philip Taylor

  DOI：10.1016/s0040-4039(00)78524-8

  日期：1994.11

  A chromium promoted acetylene-vinylidene rearrangement has been utilised in the synthesis of (+/-)-andirolactone.

  铬促进的乙炔-亚乙烯基重排已被用于（+/-）-和内酯内酯的合成中。
• General synthesis of 1-oxaspiro[4.5]decan-2-ones and 1-oxaspiro[4.5]decanes from 5-methylene-2(5H)-furanone
  作者：Daniel Alonso、Josep Font、Rosa M. Ortuno

  DOI：10.1021/jo00019a019

  日期：1991.9

  5-Methylene-2(5H)-furanone underwent Diels-Alder cycloadditions to butadiene and several acyclic and cyclic C-substituted dienes, respectively, affording bicyclic and tricyclic spiroadducts in good yields. These compounds are precursors of other unsaturated and saturated spirolactones and also spiroethers, which were obtained through simple chemical reactions, i.e., hydrogenation of C-C double bonds, reduction of the carbonyl group, and Michael addition. The synthesis of 32 spirolactones and eight spiroethers illustrates the scope and efficiency of this method. Many of these products are suitable for use as components of perfumes and aromas owing to their olfactive properties.