1,3-二溴-1,3-二氯丙酮 | 62874-84-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,3-二溴-1,3-二氯丙酮
• 英文名称: 1,3-dibromo-1,3-dichloropropanone
• 英文别名: 1,3-dibromo-1,3-dichloroacetone；1,3-dibromo-1,3-dichloro-propan-2-one；1,3-dibromo-1,3-dichloropropan-2-one
• CAS: 62874-84-4
• 化学式: C₃H₂Br₂Cl₂O
• 分子量: 284.762
• InChiKey: PMKHEKMZTWMVJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

制备方法与用途

生物活性物质1,3-二溴-1,3-二氯乙酮是一种卤化臭氧-氯和臭氧氯胺消毒副产物（DBPs），主要在使用氯或氯胺作为辅助消毒剂时，由于溴化水平升高而产生。

反应信息

• 作为反应物：
  描述：

  2-(呋喃-2-基甲基)呋喃 、 1,3-二溴-1,3-二氯丙酮 在 diethylzinc 作用下， 以 甲苯 为溶剂， 生成 meso-1,1'-methylenedi[(1R,1'S,5S,5'R)-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-1-yl] 、 (+/-)-1,1'-Methylenedi[(1RS,1'RS,5SR,5'SR)-3-oxo-8-oxabicyclo[3.2.1]oct-6-ene]
  参考文献：
  名称：

  Scope and Limitations of the Double [4+3]-Cycloadditions of 2-Oxyallyl Cations to 2,2‘-Methylenedifuran and Derivatives

  摘要：

  The reactivity of various 2-oxyallyl cations toward 2,2'-methylenedifuran (1b), 2,2'-(hydroxymethyl)difuran (1c), 2,2'-(trimethylsilylmethylene)difuran (1d), and di(2-furyl)methanone (1e) has been explored. Difuryl derivatives 1c, 1d, and le refused to undergo formal double [4+3]-cycloadditions. Conditions have been found to convert 1b into meso-1,1'-methylenedi[(1R,1'S,5S,5'R)- (3) and (+/-)-1,1'- methylenedi[(1RS, 1'SR,5SR,5'RS)-8-oxabicyclo[3.2.1]oct-6-en-3-one] (4) that do not require CF3CH(OH)CF3 as solvent. High yields of meso-1,1'-methylenedi[(1R,1'S,2S,2'R,4R,4'S,5S,5'R)- (5) and (+/-)-1,1'-methylenedi[(1RS,1'RS,2SR,2'SR,4RS,4'RS,5SR,5'SR)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6- en-3-one] (6) have been obtained when 1b was reacted with 2,4-dibromopentan-3-one (7h) and NaI/Cu.

  DOI：

  10.1021/jo020678s
• 作为产物：
  描述：

  1,3-二氯丙酮 在 氢溴酸 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 144.0h， 以58%的产率得到1,3-二溴-1,3-二氯丙酮
  参考文献：
  名称：

  Scope and Limitations of the Double [4+3]-Cycloadditions of 2-Oxyallyl Cations to 2,2‘-Methylenedifuran and Derivatives

  摘要：

  The reactivity of various 2-oxyallyl cations toward 2,2'-methylenedifuran (1b), 2,2'-(hydroxymethyl)difuran (1c), 2,2'-(trimethylsilylmethylene)difuran (1d), and di(2-furyl)methanone (1e) has been explored. Difuryl derivatives 1c, 1d, and le refused to undergo formal double [4+3]-cycloadditions. Conditions have been found to convert 1b into meso-1,1'-methylenedi[(1R,1'S,5S,5'R)- (3) and (+/-)-1,1'- methylenedi[(1RS, 1'SR,5SR,5'RS)-8-oxabicyclo[3.2.1]oct-6-en-3-one] (4) that do not require CF3CH(OH)CF3 as solvent. High yields of meso-1,1'-methylenedi[(1R,1'S,2S,2'R,4R,4'S,5S,5'R)- (5) and (+/-)-1,1'-methylenedi[(1RS,1'RS,2SR,2'SR,4RS,4'RS,5SR,5'SR)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6- en-3-one] (6) have been obtained when 1b was reacted with 2,4-dibromopentan-3-one (7h) and NaI/Cu.

  DOI：

  10.1021/jo020678s