3-(2-Bromophenyl)-1,2-dioxaspiro[3.3]heptane | 1321621-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-Bromophenyl)-1,2-dioxaspiro[3.3]heptane
• CAS: 1321621-47-9
• 化学式: C₁₁H₁₁BrO₂
• 分子量: 255.111
• InChiKey: VOTDRGQUNVFEGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-bromo-2-(cyclobutylidenemethyl)benzene 在 ammonium cerium (IV) nitrate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以56%的产率得到3-(2-Bromophenyl)-1,2-dioxaspiro[3.3]heptane
  参考文献：
  名称：

  Cerium(IV) Ammonium Nitrate–Mediated Oxidation of Mono-aryl-substituted Methylenecyclobutanes: A Convenient Method for the Synthesis of Spirocyclobutyl-1,2-dioxethanes

  摘要：

  Cerium(IV) ammonium nitrate (CAN)-mediated oxidation of methylenecyclobutanes was investigated. Compared with the similar reactions of methylenecyclopropanes, the reaction products were quite different. Instead of the desired ring-enlarged product cyclopentanones, a cyclobutyl ring-intact product, spirocyclobutyl-1,2-dioxethane, was obtained. The structures of these spiroheterocycle-containing compounds are interesting, and the reactions are potentially valuable in both organic synthesis and mechanism research.

  DOI：

  10.1080/00397911.2010.505705

文献信息

• Cerium(IV) Ammonium Nitrate–Mediated Oxidation of Mono-aryl-substituted Methylenecyclobutanes: A Convenient Method for the Synthesis of Spirocyclobutyl-1,2-dioxethanes
  作者：Lei Yu、Lingfeng Ren、Rong Yi、Rong Guo

  DOI：10.1080/00397911.2010.505705

  日期：2011.9.1

  Cerium(IV) ammonium nitrate (CAN)-mediated oxidation of methylenecyclobutanes was investigated. Compared with the similar reactions of methylenecyclopropanes, the reaction products were quite different. Instead of the desired ring-enlarged product cyclopentanones, a cyclobutyl ring-intact product, spirocyclobutyl-1,2-dioxethane, was obtained. The structures of these spiroheterocycle-containing compounds are interesting, and the reactions are potentially valuable in both organic synthesis and mechanism research.