8-Methyl-1-oxaspiro<4.5>dec-7-en-2-one | 135974-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 8-Methyl-1-oxaspiro<4.5>dec-7-en-2-one
• 英文别名: 8-Methyl-1-oxaspiro[4.5]dec-7-en-2-one
• CAS: 135974-79-7
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: SMWMCNIJUHXQLU-UHFFFAOYSA-N

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：
  0.7
• 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>dec-7-en-2-one 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 22.0h， 生成 4,8-dimethyl-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
• 作为产物：
  描述：

  8-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one 在 红铝 、 copper(I) bromide 、 正丁醇 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到8-Methyl-1-oxaspiro<4.5>dec-7-en-2-one
  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

文献信息

• Process for preparing lactones and the use thereof as odoriferous material
  申请人：KAO CORPORATION

  公开号：EP1652845B1

  公开（公告）日：2007-11-14
• Synthesis of 5,5-disubstituted 2(3H)-dihydrofuranones containing side-chain carbonyl functions, and some derivatives.
  作者：Joan Bassa、Marta Planas、Cristóbal Segura、Montserrat Ventura、Rosa M. Ortuño

  DOI：10.1016/s0040-4020(01)85296-0

  日期：1994.1

  Several title compounds containing aldehyde, ketone or unsaturated ester functions in side-chains at C-5 position have been synthesized for the first time. The ability of some of these compounds as precursors in the preparation of polyfunctional cyclopentadiene or spiro[4.4]nonane derivatives has shown to be feasible.
• 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.