6-chloromethyl-1,4-dioxan-2-one | 22901-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 6-chloromethyl-1,4-dioxan-2-one
• 英文别名: 6-(chloromethyl)-1,4-dioxan-2-one
• CAS: 22901-29-7
• 化学式: C₅H₇ClO₃
• mdl: MFCD19233105
• 分子量: 150.562
• InChiKey: WWPUUZXTUDOBDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  6-chloromethyl-1,4-dioxan-2-one 在 potassium hydrogencarbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以62%的产率得到6-methylene-1,4-dioxan-2-one
  参考文献：
  名称：

  摘要：

  3-Alkyl-6-methyl-2,3-dihydro-1,4-dioxin-2-ones reacted with acetyl chloride in the presence of zinc(II) chloride to give 5-acetyl-3-alkyl-6-methyl-2,3-dihydro-1,4-dioxin-2-ones. Oxidation of the latter with hydrogen peroxide in formic acid, followed by treatment with magnesium bromide, afforded 3-alkyl-6-methyl-1,4-dioxane-2,5-diones. Chlorination of 6-hydroxymethyl-1,4-dioxan-2-ones with thionyl chloride and subsequent dehydrochlorination led to formation of 6-methylene-1,4-dioxan-2-ones.

  DOI：

  10.1023/a:1026021631923
• 作为产物：
  描述：

  6-(hydroxymethyl)-1,4-dioxan-2-one 在 氯化亚砜 作用下， 以 吡啶 为溶剂， 以82%的产率得到6-chloromethyl-1,4-dioxan-2-one
  参考文献：
  名称：

  Synthesis of New Substituted 2,3-Dihydro-1,4-dioxin-2-ones and 1,4-Dioxan-2-ones

  摘要：

  3-Alkyl-6-methyl-2,3-dihydro-1,4-dioxin-2-ones reacted with acetyl chloride in the presence of zinc(II) chloride to give the corresponding 3-alkyl-5-acetyl-6-methyl-2,3-dihydro-1,4-dioxin-2-ones. Oxidation of the latter with hydrogen peroxide in formic acid, followed by treatment with magnesium bromide, afforded 3-alkyl-6-methyl-1,4-dioxane-2,5-diones. Successive chlorination and dechlorination of 6-hydroxymethyl-1,4-dioxan-2-ones yielded 6-methylene-1,4-dioxan-2-ones.

  DOI：

  10.1023/b:rujo.0000003199.27202.93

文献信息

• Malinovskii,M.S. et al., Soviet progress in chemistry, 1971, vol. 37, # 4, p. 48 - 51
  作者：Malinovskii,M.S. et al.

  DOI：——

  日期：——
• Synthesis of New Substituted 2,3-Dihydro-1,4-dioxin-2-ones and 1,4-Dioxan-2-ones
  作者：S. M. Akopyan、A. G. Khachatryan

  DOI：10.1023/b:rujo.0000003199.27202.93

  日期：2003.7

  3-Alkyl-6-methyl-2,3-dihydro-1,4-dioxin-2-ones reacted with acetyl chloride in the presence of zinc(II) chloride to give the corresponding 3-alkyl-5-acetyl-6-methyl-2,3-dihydro-1,4-dioxin-2-ones. Oxidation of the latter with hydrogen peroxide in formic acid, followed by treatment with magnesium bromide, afforded 3-alkyl-6-methyl-1,4-dioxane-2,5-diones. Successive chlorination and dechlorination of 6-hydroxymethyl-1,4-dioxan-2-ones yielded 6-methylene-1,4-dioxan-2-ones.
• ——
  作者：S. M. Akopyan、A. G. Khachatryan

  DOI：10.1023/a:1026021631923

  日期：——

  3-Alkyl-6-methyl-2,3-dihydro-1,4-dioxin-2-ones reacted with acetyl chloride in the presence of zinc(II) chloride to give 5-acetyl-3-alkyl-6-methyl-2,3-dihydro-1,4-dioxin-2-ones. Oxidation of the latter with hydrogen peroxide in formic acid, followed by treatment with magnesium bromide, afforded 3-alkyl-6-methyl-1,4-dioxane-2,5-diones. Chlorination of 6-hydroxymethyl-1,4-dioxan-2-ones with thionyl chloride and subsequent dehydrochlorination led to formation of 6-methylene-1,4-dioxan-2-ones.