3-氯-4-(二氯甲基)-5H-呋喃-2-酮 | 122551-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 3-氯-4-(二氯甲基)-5H-呋喃-2-酮
• 英文名称: 3-Chloro-4-(dichloromethyl)-2(5H)-furanone
• 英文别名: 4-chloro-3-(dichloromethyl)-2H-furan-5-one
• CAS: 122551-89-7
• 化学式: C₅H₃Cl₃O₂
• 分子量: 201.437
• InChiKey: WNQKLIFDPFSPIZ-UHFFFAOYSA-N

物化性质

• 溶解度：
  In water, 6,602 mg/L at 25 °C (est)
• 蒸汽压力：
  2.34X10-3 mm Hg at 25 °C (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

毒理性

• 非人类毒性摘录

遗传毒性/ 最近在氯化饮用水中确定的氯化丁烯酸的致突变活性通过沙门氏菌微体试验和SOS色测试验进行了测定。使用了沙门氏菌typhimurium测试菌株TA97、TA98和TA100，有和没有S9混合物。在SOS色测试验中，以大肠杆菌PQ37为指示生物，进行有和无代谢激活的测试。此外，通过小鼠腹腔注射处理的微核试验，研究了极其强效的Ames试验致突变物（Z）-2-氯-3-(二氯甲基)-4-氧代丁烯酸（MX，开放形式）。沙门氏菌试验和SOS色测试验的结果显示，MX是所测试化合物中最强的致突变物。MX的还原形式（Z）-2-氯-3-(二氯甲基)-4-羟基丁-2-烯酸（red-MX）和MX的几何异构体（E）-2-氯-3-(二氯甲基)-4-氧代丁烯酸（EMX）也能诱导突变。然而，由于EMX的溶液中大约含有5%的MX，它的活性大部分可能归因于MX。EMX的氧化形式（E）-2-氯-3-(二氯甲基)-丁二酸（ox-EMX）仅在SOS色测试验中略微有活性。所有这些化合物都是直接作用的致突变物，在有代谢激活（S9混合物）的情况下，它们不会产生致突变性。MX的氧化形式（Z）-2-氯-3-(二氯甲基)-丁二酸（ox-MX）在所测试的剂量水平下没有致突变性。MX没有在小鼠骨髓中诱导微核。

/GENOTOXICITY/ The mutagenic activities of the chlorinated butenoic acids recently identified in chlorinated drinking waters were determined by the Salmonella microsome assay and by the SOS chromotest. The Salmonella typhimurium tester strains TA97, TA98 and TA100 were used without and with S9 mix. In the SOS chromotest Escherichia coli PQ37 was used as an indicator organism with and without metabolic activation. In addition, the extremely potent Ames test mutagen (Z)-2-chloro-3-(dichloromethyl)-4-oxobutenoic acid (MX, in the open form), was studied by the micronucleus test with mice using intraperitoneal treatment. The results of the Salmonella assay and the SOS chromotest showed that MX was by far the most potent mutagen of the compounds tested. Mutations were also induced by the reduced form of MX, (Z)-2-chloro-3-(dichloromethyl)-4-hydroxybut-2-enoic acid (red-MX), and by the geometric isomer of MX, (E)-2-chloro-3-(dichloromethyl)-4-oxobutenoic acid (EMX). However, since the solution of EMX contained approximately 5% MX, most of its activity might be attributable to MX. The oxidised form of EMX, (E)-2-chloro-3-(dichloromethyl)-butenedioic acid (ox-EMX), was marginally active in the SOS chromotest only. All these compounds were directly acting mutagens and in the presence of metabolic activation (S9 mix) they did not generate mutagenicity. The oxidized form of MX, (Z)-2-chloro-3-(dichloromethyl)-butenedioic acid (ox-MX), was not mutagenic at the dose levels tested. MX did not induce micronuclei in the bone marrow of mice.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

遗传毒性：强致突变剂3-氯-4-(二氯甲基)-5-羟基-2(5H)-呋喃酮(MX)及其几何异构体E-2-氯-3-(二氯甲基)-4-氧代丁烯酸(E-MX)已被发现在氯化饮水中存在。MX大约占总突变性的30%，而E-MX只占几个百分点。MX和E-MX在水中的稳定性不佳，会发生pH依赖性异构化（MX与E-MX达到平衡）和水解降解。MX类似物3-氯-4-(二氯甲基)-2(5H)-呋喃酮(红-MX)和2-氯-3-(二氯甲基)-2-丁烯二酸(氧-MX)也已在氯化水中被识别。然而，这些化合物的相对较低的致突变性表明，它们对氯化水总体致突变性的贡献仅为中等程度的重要性。

/GENOTOXICITY/ The strong Ames mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2 (5H)-furanone (MX) and its geometric isomer E-2-chloro-3-(dichloromethyl)-4-oxobutenoic acid (E-MX) have been shown to be present in chlorinated drinking waters. MX accounts for approximately 30% and E-MX for a few percent of the overall mutagenicity. MX and E-MX are unstable in water and undergo both pH dependent isomerization (MX in equilibrium E-MX) and hydrolytic degradation. ... The MX analogues 3-chloro-4-(dichloromethyl)-2 (5H)-furanone (red-MX) and 2-chloro-3-(dichloromethyl)-2-butenedioic acid (ox-MX) have also been identified in chlorinated water. However, the relatively low mutagenicity of these compounds suggests that their contribution to the overall mutagenicity of chlorinated water is of only moderate significance.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

遗传毒性/ 3-氯-4-(二氯甲基)-5-羟基-2(5H)-呋喃酮(MX,化合物1)、3-氯-4-(二氯甲基)-2(5H)-呋喃酮(RMX,化合物6)和2-(二氯甲基)-3,3-二氯丙烯醛(TCB,化合物7)的致突变性在同一试验中以及使用Salmonella typhimurium (TA100)且无需微粒体活化组分的情况下进行了重复测定。此外，尽管不是与MX、RMX和TCB同时进行，但2-甲基-3,3-二氯丙烯醛(化合物8)的致突变性也以同样的方式进行了检测。本研究旨在确定MX的开环和闭环形式在其致突变性中的作用。MX的致突变性大约是开环类似物TCB的100倍，是闭环类似物RMX的10倍。化合物8无活性。... MX相对于RMX和TCB的增强致突变性归因于MX固有的致突变性，而其更大的稳定性被认为只起到了较小的作用。此外，闭环类似物RMX相对于开环类似物TCB的更大致突变性表明，尽管在试验条件下MX的开环形式占主导，但MX的环形式是活性物种。

/GENOTOXICITY/ The mutagenicities of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX, compound 1), 3-chloro-4-(dichloromethyl)-2(5H)-furanone (RMX, compound 6), and 2-(dichloromethyl)-3,3-dichloropropenal (TCB, compound 7) were determined in the same assay and in repetitive determinations using Salmonella typhimurium (TA100) without microsomal fraction activation. In addition, the mutagenicity of 2-methyl-3,3-dichloropropenal (compound 8) was assayed in the same manner although not simultaneously with MX, RMX, and TCB. This study was undertaken to ascertain the role of open- and closed-ring forms of MX in the mutagenicity of MX. MX proved to be roughly 100 times more mutagenic than the open-ring analogue TCB and 10 times more mutagenic than the closed-ring analogue RMX. Compound 8 was inactive. ... The enhanced mutagenicity of MX relative to RMX and TCB is attributed to the intrinsic mutagenicity of MX and its greater stability is judged to play only a minor role. Moreover, the greater mutagenicity of the closed-ring analogue RMX relative to the open-ring analogue TCB points to the ring form of MX as the active species even though the open form of MX is predominant under assay conditions.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

遗传毒性/ 具有与强效细菌诱变剂3-氯-4-(二氯甲基)-5-羟基-2(5H)-呋喃酮(MX)结构相似性的化合物已经被合成，并且对化合物的诱变潜力进行了初步筛选。在没有代谢激活的情况下，这些化合物在Ames试验菌株TA100中诱导了突变。所有化合物都被发现比MX的诱变作用要弱。唯一可以被认为是强诱变剂的化合物是3-氯-4-(氯甲基)-5-羟基-2(5H)-呋喃酮(CMCF)，尽管每纳摩尔的CMCF产生的回复突变体数量仅为MX的五分之一。

/GENOTOXICITY/ Compounds with structural similarities to the potent bacterial mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone, MX, have been synthesized and ... a preliminary screening of the mutagenic potency of the compounds was performed. ... The compounds induced mutagenicity in Ames tester strain TA100 in tests performed without metabolic activation. All the compounds were found to be less potent mutagens than MX. The only compound which could be considered as a strong mutagen was 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone (CMCF), although the revertants per nanomole of CMCF was only one-fifth of the revertants /for MX/.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  3-氯-4-(二氯甲基)-5H-呋喃-2-酮 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 盐酸 、 水 作用下， 以 四氯化碳 、 1,4-二氧六环 为溶剂， 反应 26.0h， 以50%的产率得到3-氯-4-(二氯甲基)-5-羟基-2(5H)-呋喃酮
  参考文献：
  名称：

  Facile synthesis of mutagen X (MX): 3-chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one

  摘要：

  3-Chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one (mutagen X, MX) was synthesized in six steps from commercially-available and inexpensive starting materials (27% overall yield). This synthesis enables the preparation of MX analogs and does not require the use of chlorine gas, as do previously reported methods. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.044
• 作为产物：
  描述：

  4-chloro-3-(hydroxymethyl)-2H-furan-5-one 在 pyridinium chlorochromate 、 sodium chloride 、 五氯化磷 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.33h， 以80%的产率得到3-氯-4-(二氯甲基)-5H-呋喃-2-酮
  参考文献：
  名称：

  Facile synthesis of mutagen X (MX): 3-chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one

  摘要：

  3-Chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one (mutagen X, MX) was synthesized in six steps from commercially-available and inexpensive starting materials (27% overall yield). This synthesis enables the preparation of MX analogs and does not require the use of chlorine gas, as do previously reported methods. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.044

文献信息

• Organic waste treatment
  申请人：——

  公开号：US20040251197A1

  公开（公告）日：2004-12-16

  A method of treatment of sewage comprising adding at least one cell signalling chemical (CSC) to a sewage substrate, wherein the at least one CSC regulates activity of a microbial population in the sewage substrate. In particular, methods of reducing odour in sewage treatment systems, preventing corrosion in sewage treatment systems, enhancing microbial digestion of sewage, managing methane gas production in a sewage treatment system, enhancing digestion of sewage sludge, resuscitating dormant microbes or microbes that are in a starvation or stationary phase in a sewage substrate and controlling the bacteria responsible for oxidation or reduction of nitrogenous compounds in a sewage substrate, are provided.

  一种污水处理方法，包括向污水基质中添加至少一种细胞信号化学物（CSC），其中至少一种 CSC 可调节污水基质中微生物种群的活性。特别是提供了减少污水处理系统中的臭味、防止污水处理系统中的腐蚀、加强污水的微生物消化、管理污水处理系统中甲烷气体的产生、加强污水污泥的消化、恢复污水基质中休眠的微生物或处于饥饿或静止阶段的微生物以及控制污水基质中负责氧化或还原含氮化合物的细菌的方法。
• Potentially mutagenic, chorine-substituted 2(5H)-furanones: studies of their synthesis and NMR properties
  作者：Robert T. LaLonde、Hannu Perakyla、Michael P. Hayes

  DOI：10.1021/jo00296a053

  日期：1990.4
• LALONDE, ROBERT T.;PERAKYLA, HANNU;HAYES, MICHAEL P., J. ORG. CHEM., 55,(1990) N, C. 2847-2855
  作者：LALONDE, ROBERT T.、PERAKYLA, HANNU、HAYES, MICHAEL P.

  DOI：——

  日期：——
• US7473363B2
  申请人：——

  公开号：US7473363B2

  公开（公告）日：2009-01-06
• Facile synthesis of mutagen X (MX): 3-chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one
  作者：Venkata Velvadapu、Mark E. McDonnell、Eileen K. Jaffe、Allen B. Reitz

  DOI：10.1016/j.tetlet.2012.04.044

  日期：2012.6

  3-Chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one (mutagen X, MX) was synthesized in six steps from commercially-available and inexpensive starting materials (27% overall yield). This synthesis enables the preparation of MX analogs and does not require the use of chlorine gas, as do previously reported methods. (C) 2012 Elsevier Ltd. All rights reserved.