3-chloro-5-(dichloromethyl)-5-hydroxy-2-furanone | 154180-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-chloro-5-(dichloromethyl)-5-hydroxy-2-furanone
• 英文别名: 2(5H)-Furanone, 3-chloro-5-(dichloromethyl)-5-hydroxy-；3-chloro-5-(dichloromethyl)-5-hydroxyfuran-2-one
• CAS: 154180-04-8
• 化学式: C₅H₃Cl₃O₃
• 分子量: 217.436
• InChiKey: MTUBTRJWNBOSSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  441.2±45.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-5-(dichloromethyl)-5-hydroxy-2-furanone 在 硫酸 作用下， 反应 1.0h， 以53%的产率得到3-Chloro-5-dichloromethylene-2-furanone
  参考文献：
  名称：

  Occurrence of Some Chlorinated Enol Lactones and Cyclopentene-1,3-Diones in Chlorine-Treated Waters

  摘要：

  Enol lactones (5-dichloromethylene-2-furanones) and 2,2-dichlorocyclopentene-1,3-diones, a total of six compounds, were synthesized and subsequently qualitatively and quantitatively determined in a sample of chlorination stage liquor from the bleaching of softwood kraft pulp (CBL), in chlorine-treated natural humic water (HW), and in three samples of drinking water treated with various disinfectants (DW1-3). All the compounds could be observed in the samples, in concentrations ranging from 2 to 170 mu g/L in CBL, from 7 to 65 ng/L in HW, and at most a few nanograms per liter in DW1-3. The compounds were found to be weakly mutagenic in the Ames assay (strain TA100 without metabolic activation). The contribution of the compounds to the total mutagenicity in the studied samples was negligible. The compounds were unstable in aqueous solutions at pH 7.0, and under these conditions they were in part converted to 5-(dichloromethyl)-5-hydroxy-2-furanones In acidified methanol, the enol lactones were partially converted to 5-(dichloromethyl)-5-methoxy-2-furanones.

  DOI：

  10.1021/es00007a022
• 作为产物：
  描述：

  2,2,4-trichloro-4-cyclopentene-1,3-dione 在 potassium carbonate 作用下， 以 乙醚 为溶剂， 反应 0.02h， 以20%的产率得到3-chloro-5-(dichloromethyl)-5-hydroxy-2-furanone
  参考文献：
  名称：

  氯化的5-羟基-5-甲基-2-呋喃酮的合成方法

  摘要：

  描述了在C-5具有单，二和三氯甲基的氯化的5-羟基呋喃酮的合成。通过乙酰丙酸的氯化，然后三乙胺促进的氯化氢消除，获得了5-氯甲基羟基呋喃酮。氯化4-环戊烯-1，3-二酮的水解产生5-二氯甲基羟基呋喃酮。通过三氯乙酸钠的热分解将三氯甲基结合到马来酸酐中。

  DOI：

  10.1016/s0040-4020(01)80248-9

文献信息

• Synthetic approaches to chlorinated 5-hydroxy-5-methyl-2-furanones
  作者：Robert Franzén、Leif Kronberg

  DOI：10.1016/s0040-4020(01)80248-9

  日期：1993.1

  The syntheses of chlorinated 5 - hydroxy- furanones with a mono-, di-, and trichloromethyl group at C-5 are described. The 5-chloromethyl hydroxyfuranones were obtained by chlorination of levulinic acid followed by triethylamine promoted elimination of hydrogen chloride. Hydrolyses of chlorinated 4 - cyclopentene- 1,3 -diones yielded 5-dichloromethyl hydroxyfuranones. The trichloromethyl group was

  描述了在C-5具有单，二和三氯甲基的氯化的5-羟基呋喃酮的合成。通过乙酰丙酸的氯化，然后三乙胺促进的氯化氢消除，获得了5-氯甲基羟基呋喃酮。氯化4-环戊烯-1，3-二酮的水解产生5-二氯甲基羟基呋喃酮。通过三氯乙酸钠的热分解将三氯甲基结合到马来酸酐中。
• Occurrence of Some Chlorinated Enol Lactones and Cyclopentene-1,3-Diones in Chlorine-Treated Waters
  作者：Annika. Smeds、Robert. Franzen、Leif. Kronberg

  DOI：10.1021/es00007a022

  日期：1995.7.1

  Enol lactones (5-dichloromethylene-2-furanones) and 2,2-dichlorocyclopentene-1,3-diones, a total of six compounds, were synthesized and subsequently qualitatively and quantitatively determined in a sample of chlorination stage liquor from the bleaching of softwood kraft pulp (CBL), in chlorine-treated natural humic water (HW), and in three samples of drinking water treated with various disinfectants (DW1-3). All the compounds could be observed in the samples, in concentrations ranging from 2 to 170 mu g/L in CBL, from 7 to 65 ng/L in HW, and at most a few nanograms per liter in DW1-3. The compounds were found to be weakly mutagenic in the Ames assay (strain TA100 without metabolic activation). The contribution of the compounds to the total mutagenicity in the studied samples was negligible. The compounds were unstable in aqueous solutions at pH 7.0, and under these conditions they were in part converted to 5-(dichloromethyl)-5-hydroxy-2-furanones In acidified methanol, the enol lactones were partially converted to 5-(dichloromethyl)-5-methoxy-2-furanones.

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