4-methylene-5,5-dimethyl-1,2-dioxolan-3-one | 104848-77-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 4-methylene-5,5-dimethyl-1,2-dioxolan-3-one
• 英文别名: 1,2-Dioxolan-3-one, 5,5-dimethyl-4-methylene-；5,5-dimethyl-4-methylidenedioxolan-3-one
• CAS: 104848-77-3
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: PGFKTCGXTADJDX-UHFFFAOYSA-N

物化性质

• 沸点：
  44-47 °C(Press: 0.1 Torr)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methylene-5,5-dimethyl-1,2-dioxolan-3-one 在 三苯基膦 作用下， 以 氯仿 为溶剂， 生成 4,4-Dimethyl-3-methylene-1-oxetan-2-one
  参考文献：
  名称：

  Synthesis of .alpha.-methylene .beta.-lactones, novel heterocycles

  摘要：

  Triphenylphosphine deoxygenation of beta-alkyl, beta,beta-dialkyl-, and beta,beta-spirocycloalkyl-substituted alpha-methylene-beta-peroxy lactones 3a-k, which are readily available by photooxygenation of the corresponding alpha,beta-unsaturated carboxylic acids 1, and cyclization of the resulting alpha-methylene-beta-hydroperoxy acids 2 constitute a convenient method for the preparation of a variety of alpha-methylene beta-lactones 5. Alternatively, the alpha-methylene-beta-hydroxy carboxylic acids 4 can be directly cyclized by benzenesulfonyl chloride in pyridine into these novel four-membered ring heterocycles 5.

  DOI：

  10.1021/jo00020a016
• 作为产物：
  描述：

  2,3-二甲基丁-2-烯酸 在 氧气 、 tetraphenylporphyrin 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 12.0h， 以91%的产率得到4-methylene-5,5-dimethyl-1,2-dioxolan-3-one
  参考文献：
  名称：

  On the reaction of .alpha.-methylene-.beta.-peroxy lactones with olefins

  摘要：

  DOI：

  10.1021/jo00373a029

文献信息

• Intrazeolite Photooxidations of Electron-Poor Alkenes
  作者：Edward L. Clennan、Jakub P. Sram、Andrea Pace、Katie Vincer、Sophia White

  DOI：10.1021/jo025657c

  日期：2002.5.1

  The inability of the intrazeolite environment to influence the regiochemistry of addition of singlet oxygen to electron-poor olefins is reported. This divergent behavior with respect to electron-rich alkenes is rationalized with a multicomplexation model that emphasizes the importance of intrazeolite substrate-cation binding.
• ADAM W.; GRIESBECK A.; KAPPES D., J. ORG. CHEM., 51,(1986) N 23, 4479-4481
  作者：ADAM W.、 GRIESBECK A.、 KAPPES D.

  DOI：——

  日期：——
• On the reaction of .alpha.-methylene-.beta.-peroxy lactones with olefins
  作者：Waldemar Adam、Axel Griesbeck、Dag Kappes

  DOI：10.1021/jo00373a029

  日期：1986.11
• Synthesis of .alpha.-methylene .beta.-lactones, novel heterocycles
  作者：Waldemar Adam、Rainer Albert、Nuria Dachs Grau、Ludwig Hasemann、Bernd Nestler、Eva Maria Peters、Karl Peters、Frank Prechtl、Hans Georg Von Schnering

  DOI：10.1021/jo00020a016

  日期：1991.9

  Triphenylphosphine deoxygenation of beta-alkyl, beta,beta-dialkyl-, and beta,beta-spirocycloalkyl-substituted alpha-methylene-beta-peroxy lactones 3a-k, which are readily available by photooxygenation of the corresponding alpha,beta-unsaturated carboxylic acids 1, and cyclization of the resulting alpha-methylene-beta-hydroperoxy acids 2 constitute a convenient method for the preparation of a variety of alpha-methylene beta-lactones 5. Alternatively, the alpha-methylene-beta-hydroxy carboxylic acids 4 can be directly cyclized by benzenesulfonyl chloride in pyridine into these novel four-membered ring heterocycles 5.