5-p-bromophenacyl-2,2-dimethyl-5-chloro-1,3-dioxane-4,6-dione | 135578-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-p-bromophenacyl-2,2-dimethyl-5-chloro-1,3-dioxane-4,6-dione
• 英文别名: 2,2-dimethyl-5-(p-bromophenacyl)-5-chloro-1,3-dioxane-4,6-dione；5-[2-(4-Bromophenyl)-2-oxoethyl]-5-chloro-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 135578-10-8
• 化学式: C₁₄H₁₂BrClO₅
• mdl: MFCD00827929
• 分子量: 375.603
• InChiKey: TWSAAORAWFLYSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-p-bromophenacyl-2,2-dimethyl-5-chloro-1,3-dioxane-4,6-dione 在 水 、 溶剂黄146 作用下， 反应 1.5h， 以68%的产率得到(2E)-4-(4-溴苯基)-4-氧代丁2-烯酸
  参考文献：
  名称：

  Meldrum's acid ? A reagent for the synthesis of unsaturated ?-lactones and ?-acylacrylic acids

  摘要：

  The thermal cyclization of 2,2-dimethyl-5-(2-aryl-2-oxoethyl)-1,3-dioxan-4,6-diones forms 5-aryl-beta, gamma-butenolides. Regioselective chlorination of 2,2-di-methyl-5-[2-aryl(alkyl)-2-oxoethyl]-1,3-dioxane-4,6-diones by SO2Cl2 gives the 5-chloro derivatives; these are cleaved by aqueous AcOH to the E-beta-acylacrylic acids, which are synthones for unsaturated gamma-lactones.

  DOI：

  10.1007/bf00961384
• 作为产物：
  描述：

  2,2-dimethyl-4,6-dioxo-5-(p-bromophenacyl)-1,3-dioxane 在 potassium bromate 、 三甲基氯硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以90%的产率得到5-p-bromophenacyl-2,2-dimethyl-5-chloro-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Chlorinating properties of the trimethylchlorosilane-potassium bromate-DMF system

  摘要：

  Beta-dicarbonyl compounds such as ethyl acetoacetate, dimedone, and Meldrum's acid derivatives undergo monochlorination by the action of a mixture of ClSiMe3 and KBrO3 in DMF at approximately 20-degrees-C.

  DOI：

  10.1007/bf00869533

文献信息

• Chlorinating properties of the trimethylchlorosilane-potassium bromate-DMF system
  作者：S. I. Zav'yalov、I. V. Sitkareva、G. I. Ezhova

  DOI：10.1007/bf00869533

  日期：1992.2

  Beta-dicarbonyl compounds such as ethyl acetoacetate, dimedone, and Meldrum's acid derivatives undergo monochlorination by the action of a mixture of ClSiMe3 and KBrO3 in DMF at approximately 20-degrees-C.
• Meldrum's acid ? A reagent for the synthesis of unsaturated ?-lactones and ?-acylacrylic acids
  作者：S. I. Zav'yalov、A. G. Zavozin、N. E. Kravchenko

  DOI：10.1007/bf00961384

  日期：1991.5

  The thermal cyclization of 2,2-dimethyl-5-(2-aryl-2-oxoethyl)-1,3-dioxan-4,6-diones forms 5-aryl-beta, gamma-butenolides. Regioselective chlorination of 2,2-di-methyl-5-[2-aryl(alkyl)-2-oxoethyl]-1,3-dioxane-4,6-diones by SO2Cl2 gives the 5-chloro derivatives; these are cleaved by aqueous AcOH to the E-beta-acylacrylic acids, which are synthones for unsaturated gamma-lactones.
• Chlorination ofβ-dicarbonyl compounds
  作者：S. I. Zav'yalov、G. I. Ezhova、I. V. Sitkareva

  DOI：10.1007/bf00780549

  日期：1993.10