(rac)-4-benzyl-2-oxaspiro[4.7]dodecane-1,9-dione | 1383572-00-6

• 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: (rac)-4-benzyl-2-oxaspiro[4.7]dodecane-1,9-dione
• 英文别名: 4-Benzyl-2-oxaspiro[4.7]dodecane-1,9-dione；4-benzyl-2-oxaspiro[4.7]dodecane-1,9-dione
• CAS: 1383572-00-6
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: PHEIDAVJARVCSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氧代环戊羧酸乙酯 在 4-二甲氨基吡啶 、 三正丁基氢锡 、 sodium hydride 、 1,1'-偶氮(氰基环己烷) 作用下， 以 二甲基亚砜 、 氯苯 、 甲苯 为溶剂， 反应 60.0h， 生成 (rac)-4-benzyl-2-oxaspiro[4.7]dodecane-1,9-dione
  参考文献：
  名称：

  Synthesis of Spirocyclic γ-Lactones by Cascade Beckwith–Dowd Ring Expansion/Cyclization

  摘要：

  A range of spirocyclic gamma-lactones have been prepared exploiting a Beckwith-Dowd ring expansion cascade involving 1-, 3-, 4-, and 5-carbon expansion of cyclopentanone and cyclohexanone followed by 5-exo-trig or 5-exo-dig cyclization. This radical cascade reaction can be achieved with various substrates to provide a broad range of gamma-lactones spirofused to 6- to 10-membered cycloalkanones.

  DOI：

  10.1021/ol301386k

文献信息

• Synthesis of Spirocyclic γ-Lactones by Cascade Beckwith–Dowd Ring Expansion/Cyclization
  作者：Judith Hierold、David W. Lupton

  DOI：10.1021/ol301386k

  日期：2012.7.6

  A range of spirocyclic gamma-lactones have been prepared exploiting a Beckwith-Dowd ring expansion cascade involving 1-, 3-, 4-, and 5-carbon expansion of cyclopentanone and cyclohexanone followed by 5-exo-trig or 5-exo-dig cyclization. This radical cascade reaction can be achieved with various substrates to provide a broad range of gamma-lactones spirofused to 6- to 10-membered cycloalkanones.