4,4-Dimethyl-1,3-dioxolan | 13372-33-3

• 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: 4,4-Dimethyl-1,3-dioxolan
• 英文别名: 4,4-dimethyl-1,3-dioxolane
• CAS: 13372-33-3
• 化学式: C₅H₁₀O₂
• 分子量: 102.133
• InChiKey: MVYGFAZZLWOFNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  重氮甲烷 、 3,3-Dimethyl-1,2-dioxetan 以 乙醚 为溶剂， 反应 22.0h， 以71%的产率得到4,4-Dimethyl-1,3-dioxolan
  参考文献：
  名称：

  1,3-Dioxolane Formation by Nucleophilic Attack of Diazoalkanes on the Peroxide Bond of 1,2-Dioxetanes

  摘要：

  The reaction of the 1,2-dioxetanes 1a-d with the diazoalkanes 2 alpha-eta was investigated. The two 3,3-disubstituted (3,3-dimethyl- and 3-(bromomethyl)-3-phenyl) dioxetanes (1a and 1b), trimethyldioxetane (1c), and tetramethyldioxetane (1d) gave with the various diazoalkanes 2 the corresponding 1,3-dioxolanes 3 (insertion products) and/or the dioxetane-derived ketones 4 (fragmentation). Nucleophilic attack by the negatively charged carbon pole of the diazoalkane on the sterically less hindered site of the dioxetane peroxide bond affords the 1,3-dioxolane 3 after cyclization with denitrogenation of the resulting O,N dipole. The O,C dipole, formed by the nucleophilic attack of the negatively charged nitrogen pole on the dioxetane, is proposed as precursor to the ketones 4 through Grob-type fragmentation with regeneration of the diazoalkane.

  DOI：

  10.1021/jo00083a027

文献信息

• Adam Waldemar, Treiber Alexander, J. Org. Chem, 59 (1994) N 4, S 840-844
  作者：Adam Waldemar, Treiber Alexander

  DOI：——

  日期：——
• 1,3-Dioxolane Formation by Nucleophilic Attack of Diazoalkanes on the Peroxide Bond of 1,2-Dioxetanes
  作者：Waldemar Adam、Alexander Treiber

  DOI：10.1021/jo00083a027

  日期：1994.2

  The reaction of the 1,2-dioxetanes 1a-d with the diazoalkanes 2 alpha-eta was investigated. The two 3,3-disubstituted (3,3-dimethyl- and 3-(bromomethyl)-3-phenyl) dioxetanes (1a and 1b), trimethyldioxetane (1c), and tetramethyldioxetane (1d) gave with the various diazoalkanes 2 the corresponding 1,3-dioxolanes 3 (insertion products) and/or the dioxetane-derived ketones 4 (fragmentation). Nucleophilic attack by the negatively charged carbon pole of the diazoalkane on the sterically less hindered site of the dioxetane peroxide bond affords the 1,3-dioxolane 3 after cyclization with denitrogenation of the resulting O,N dipole. The O,C dipole, formed by the nucleophilic attack of the negatively charged nitrogen pole on the dioxetane, is proposed as precursor to the ketones 4 through Grob-type fragmentation with regeneration of the diazoalkane.