3-((1R^*,2S^*,4R^*)-2-Hydroxybicyclo<2.2.2>oct-5-en-2-yl)propanoic acid 1,4-lactone | 130619-40-8

• 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: 3-((1R^*,2S^*,4R^*)-2-Hydroxybicyclo<2.2.2>oct-5-en-2-yl)propanoic acid 1,4-lactone
• 英文别名: (1SR, 2RS, 4SR)-3-(2-hydroxybicyclo<2.2.2>oct-5-en-2-yl)prop-2-enoic acid lactone；(1SR, 2SR, 4SR)-3-(2-hydroxybicyclo<2.2.2>oct-5-en-2-yl)prop-2-enoic acid lactone；(1S,4S,5S)-spiro[bicyclo[2.2.2]oct-2-ene-5,5'-furan]-2'-one
• CAS: 130619-40-8；130696-40-1
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: NEAPZIJSTUZLBR-IQJOONFLSA-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：
  4.0
• 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：

  3-((1R^*,2S^*,4R^*)-2-Hydroxybicyclo<2.2.2>oct-5-en-2-yl)propanoic acid 1,4-lactone 在 palladium on activated charcoal 氢气 作用下， 以100%的产率得到3-(2-Hydroxybicyclo[2.2.2]octan-2-yl)propanoic acid 1,4-lactone
  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 、 1,3-环己二烯 以 二氯甲烷 为溶剂， 反应 70.2h， 生成 3-((1R^*,2S^*,4R^*)-2-Hydroxybicyclo<2.2.2>oct-5-en-2-yl)propanoic acid 1,4-lactone
  参考文献：
  名称：

  具有环二烯的Diels-Alder反应中的5-亚甲基-2（5 ）-呋喃酮：内/外选择性

  摘要：

  已经研究了5-亚甲基-2（5 ）-呋喃酮1与环状二烯的反应中的内/外选择性。环戊二烯之间的环加成反应的动力学和理论研究都可以解释所观察到的选择性，这是对该过程进行动力学控制的直接结果。

  DOI：

  10.1016/s0040-4020(01)86771-5

文献信息

• 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.
• 5-Methylene-2(5H)-furanone in Diels-Alder reactions with cyclic dienes: endo/exo selectivity
  作者：Daniel Alonzo、Vicen¢ Branchadell、Josep Font、Antonio Oliva、Rosa M. Ortuño、Francisco Sánchez-Ferrando

  DOI：10.1016/s0040-4020(01)86771-5

  日期：——

  Endo/exo selectivity in the reactions of 5-methylene-2(5)-furanone, 1, with cyclic dienes has been investigated. Both the kinetic and theoretical studies of the cycloaddition between and cyclopentadiene have permitted to explain the observed selectivity as a direct consequence of a kinetic control over the process.

  已经研究了5-亚甲基-2（5 ）-呋喃酮1与环状二烯的反应中的内/外选择性。环戊二烯之间的环加成反应的动力学和理论研究都可以解释所观察到的选择性，这是对该过程进行动力学控制的直接结果。