6,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one | 126036-63-3

• 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: 6,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one
• 英文别名: 6,8-Dimethyl-1-oxaspiro[4.5]deca-3,7-dien-2-one
• CAS: 126036-63-3
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: KGWAWRXTGCXUJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  6,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one 在 palladium on activated charcoal 氢气 作用下， 以99%的产率得到6,8-Dimethyl-1-oxaspiro<4.5>decan-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
• 作为产物：
  描述：

  原白头翁素 、 trans-2-甲基戊二烯 在 对苯二酚 作用下， 反应 4.0h， 以80%的产率得到6,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-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

• 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：——
• 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.
• 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.