1,5-二氯-2,3-二甲氧基苯 | 90283-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,5-二氯-2,3-二甲氧基苯
• 英文名称: 3,5-dichloro-1,2-dimethoxybenzene
• 英文别名: 1,5-Dichloro-2,3-dimethoxybenzene
• CAS: 90283-01-5
• 化学式: C₈H₈Cl₂O₂
• 分子量: 207.056
• InChiKey: BCWABYVHGXOWHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-二氯-2,3-二甲氧基苯 在 硝酸 、 乙酸酐 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 40.0h， 生成 2,3-dimethoxy-1,7,8-trichlorodibenzo-p-dioxin
  参考文献：
  名称：

  Synthesis of oxygenated derivatives of 2,3,7,8-tetrachlorodibenzo-p-dioxin

  摘要：

  Four monomethoxy, five dimethoxy and four dihydroxy derivatives of polychlorodibenzo-p-dioxin been synthesized, and their physical and spectral properties (NMR and MS) have been reported. The general method for the synthesis of specific mono- and dimethoxy derivatives in reasonable yields has been found to be the condensation of 4,5-dichlorocatechol with appropriately substituted o-chloro-nitrobenzenes. The monomethoxy derivatives thus prepared were demethylated by boron tribromide-dimethyl sulfide. Several mono- and dihydroxypolychlorodibenzo-p-dioxins have been identified as metabolites of the highly toxic environmental contaminant 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). However, most of these metabolites have not been fully characterized due to the lack of appropriate standards. The availability of these synthetic oxygenated derivatives of TCDD can be used to establish the structure and the potential toxicity associated with these metabolites.

  DOI：

  10.1021/jf00033a030
• 作为产物：
  描述：

  3,5-二氯儿茶酚 、 硫酸二甲酯 在 sodium hydroxide 作用下， 反应 4.0h， 以50%的产率得到1,5-二氯-2,3-二甲氧基苯
  参考文献：
  名称：

  Synthesis of oxygenated derivatives of 2,3,7,8-tetrachlorodibenzo-p-dioxin

  摘要：

  Four monomethoxy, five dimethoxy and four dihydroxy derivatives of polychlorodibenzo-p-dioxin been synthesized, and their physical and spectral properties (NMR and MS) have been reported. The general method for the synthesis of specific mono- and dimethoxy derivatives in reasonable yields has been found to be the condensation of 4,5-dichlorocatechol with appropriately substituted o-chloro-nitrobenzenes. The monomethoxy derivatives thus prepared were demethylated by boron tribromide-dimethyl sulfide. Several mono- and dihydroxypolychlorodibenzo-p-dioxins have been identified as metabolites of the highly toxic environmental contaminant 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). However, most of these metabolites have not been fully characterized due to the lack of appropriate standards. The availability of these synthetic oxygenated derivatives of TCDD can be used to establish the structure and the potential toxicity associated with these metabolites.

  DOI：

  10.1021/jf00033a030

文献信息

• Halogenated volatiles from the fungus <i>Geniculosporium</i> and the actinomycete <i>Streptomyces chartreusis</i>
  作者：Tao Wang、Patrick Rabe、Christian A Citron、Jeroen S Dickschat

  DOI：10.3762/bjoc.9.311

  日期：——

  Two unidentified chlorinated volatiles X and Y were detected in headspace extracts of the fungus Geniculosporium. Their mass spectra pointed to the structures of a chlorodimethoxybenzene for X and a dichlorodimethoxybenzene for Y. The mass spectra of some constitutional isomers for X and Y were included in our databases and proved to be very similar, thus preventing a full structural assignment. For unambiguous structure elucidation all possible constitutional isomers for X and Y were obtained by synthesis or from commercial suppliers. Comparison of mass spectra and GC retention times rigorously established the structures of the two chlorinated volatiles. Chlorinated volatiles are not very widespread, but brominated or even iodinated volatiles are even more rare. Surprisingly, headspace extracts from Streptomyces chartreusis contained methyl 2-iodobenzoate, a new natural product that adds to the small family of iodinated natural products.

  在真菌Geniculosporium的头空间提取物中检测到了两种未经鉴定的氯化挥发性化合物X和Y。它们的质谱指向X为氯二甲氧基苯，Y为二氯二甲氧基苯的结构。X和Y的一些构造异构体的质谱已包含在我们的数据库中，证明它们非常相似，因此无法完全确定结构。为了明确结构，我们通过合成或从商业供应商处获得了X和Y的所有可能的构造异构体。质谱和气相色谱保留时间的比较严格确定了这两种氯化挥发性化合物的结构。氯化挥发性化合物并不是很常见，但溴化或甚至碘化的挥发性化合物更为罕见。令人惊讶的是，从Streptomyces chartreusis的头空间提取物中发现了甲基2-碘苯甲酸酯，这是一种新的天然产物，丰富了碘化天然产物家族。
• 13C and17O NMR study of methoxy groups in chlorinated Di- and trimethoxybenzenes
  作者：J. Knuutinen、E. Kolehmainen

  DOI：10.1002/mrc.1260280407

  日期：1990.4

  and 1,4‐dimethoxybenzenes, 1,2,3‐trimethoxybenzenes and most of their chlorinated derivatives and some related brominated compounds were measured for CDCl3 solutions. The 17O NMR chemical shifts show up to 60 ppm dispersion. Comparison between the compounds with and without adjacent chlorine atoms (2,6‐di‐ and 2,4,6‐tri‐substitution) also showed a clear methoxy carbon chemical shift change. The number

  异构体 1,2-、1,3- 和 1,4-二甲氧基苯、1,2,3-三甲氧基苯及其大部分氯化衍生物中甲氧基的 13C 和 17O NMR 数据 [化学位移和 1J(CH) 值]并对CDCl3 溶液中的一些相关溴化化合物进行了测量。17O NMR 化学位移显示高达 60 ppm 的分散。具有和不具有相邻氯原子（2,6-二取代和 2,4,6-三取代）的化合物之间的比较也显示出明显的甲氧基碳化学位移变化。如果甲氧基与芳香平面共面，则芳香环中氯原子的数量和位置对甲氧基的 17O NMR 化学位移产生很小但可观察到的影响。类似地，替代的程度和性质对 1J(CH) 直接耦合值的影响很小（约 1 Hz）。
• Smith, John R. Lindsay; McKeer, Linda C.; Taylor, Jonathan M., Journal of the Chemical Society. Perkin transactions II, 1988, p. 385 - 392
  作者：Smith, John R. Lindsay、McKeer, Linda C.、Taylor, Jonathan M.

  DOI：——

  日期：——
• Mass spectra of chlorinated veratroles (1,2-dimethoxybenzenes)
  作者：J. Knuutinen、I. O. O. Korhonen

  DOI：10.1002/oms.1210220204

  日期：1987.2

  AbstractThe behaviour of all nine chlorinated veratroles (1,2‐dimethoxybenzenes) under electron impact has been investigated. The most common fragmentation processes are interpreted using metastable ion analysis and deuterium labelled compounds. For all compounds studied, the most common fragmentation route seems to be the primary loss of a methyl radical followed by loss of carbon monoxide. The ion formed has a well‐known quinonoid structure and fragments by several routes elucidated by metastable ion analysis. In general, the spectra of the positional isomers are shown to be practically similar and it is apparent that e.g. the 3‐ and 4‐chloro isomers can be differentiated only from the abundance ratio of the [MCH3COCH3]+ and [MCH3COH2O]+ ions.
• Synthesis of oxygenated derivatives of 2,3,7,8-tetrachlorodibenzo-p-dioxin
  作者：Sudhir K. Singh、Subodh. Kumar

  DOI：10.1021/jf00033a030

  日期：1993.9.1

  Four monomethoxy, five dimethoxy and four dihydroxy derivatives of polychlorodibenzo-p-dioxin been synthesized, and their physical and spectral properties (NMR and MS) have been reported. The general method for the synthesis of specific mono- and dimethoxy derivatives in reasonable yields has been found to be the condensation of 4,5-dichlorocatechol with appropriately substituted o-chloro-nitrobenzenes. The monomethoxy derivatives thus prepared were demethylated by boron tribromide-dimethyl sulfide. Several mono- and dihydroxypolychlorodibenzo-p-dioxins have been identified as metabolites of the highly toxic environmental contaminant 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). However, most of these metabolites have not been fully characterized due to the lack of appropriate standards. The availability of these synthetic oxygenated derivatives of TCDD can be used to establish the structure and the potential toxicity associated with these metabolites.

表征谱图