2-chloro-1,4-dimethoxy-5,6-dimethylbenzene | 158669-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-1,4-dimethoxy-5,6-dimethylbenzene
• 英文别名: 1-Chloro-2,5-dimethoxy-3,4-dimethylbenzene
• CAS: 158669-22-8
• 化学式: C₁₀H₁₃ClO₂
• 分子量: 200.665
• InChiKey: RKRVZAPFTSGBCO-UHFFFAOYSA-N

物化性质

• 沸点：
  283.7±35.0 °C(predicted)
• 密度：
  1.102±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-chloro-1,4-dimethoxy-5,6-dimethylbenzene 在 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 乙酰氯 、 三氟乙酸 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 408.0h， 生成 2-(aminomethyl)-3-chloro-5,6-dimethyl-2,5-cyclohexadiene-1,4-dione hydrochloride
  参考文献：
  名称：

  醌铵盐的一般合成

  摘要：

  已经开发了将取代的对二甲氧基苯转化为醌铵盐的三步程序。用该程序制备了五个醌铵盐的例子。在第一步中，芳族物质与 N-(羟甲基)三氟乙酰胺和三氟乙酸反应。然后将三氟乙酰胺产物氧化去甲基化，最后水解得到醌铵盐。

  DOI：

  10.1055/s-2005-865296
• 作为产物：
  描述：

  1,4-二甲氧基-2,3-甲基苯 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 2-chloro-1,4-dimethoxy-5,6-dimethylbenzene
  参考文献：
  名称：

  Cation Radicals as Intermediates in Aromatic Halogenation with Iodine Monochloride: Solvent and Salt Effects on the Competition between Chlorination and Iodination

  摘要：

  Three distinct classes of substitutional reactivity can be discerned in the halogenation of a series of methyl-substituted methoxybenzenes (ArH) with iodine monochloride (ICl), namely, exclusive iodination, exclusive chlorination, and mixed iodination/chlorination. Spectral studies establish the prior formation of the charge-transfer complex [ArH,ICl] which suffers electron transfer to afford the reactive triad [ArH.+, I-., Cl-] according to Scheme 1. Separate reactivity studies show that chlorination and iodination can result from the quenching of the aromatic cation radical by chloride and iodine (atom), respectively. Iodination versus chlorination thus represents the competition between radical-pair and ion-pair collapse from the reactive triad, and it is predictably modulated by solvent polarity and added salt.

  DOI：

  10.1021/jo00100a025

文献信息

• Unexpected dimeric products from the amidomethylation of pentasubstituted benzenes
  作者：David Wiedenfeld、Mark A. Minton、Vladimir N. Nesterov、David R. Glass、Crystal L. Montoya

  DOI：10.1016/j.tetlet.2004.03.175

  日期：2004.5

  An isomeric series of unexpected diarylmethane products with flexible substituents, isolated from amidomethylation reactions of p-dimethoxybenzene derivatives, was analyzed by X-ray crystallography to reveal novel solid-state structures, two of which have identical elemental cell parameters.

  异构体系列意想不到二芳基甲烷产品具有灵活的取代基，从反应amidomethylation分离p -dimethoxybenzene衍生物，通过X射线晶体学分析以揭示新颖的固态结构，其中两个具有相同的元素细胞参数。
• Radical cation mechanism of aromatic halogenation by halogens or iodine chloride in 1,1,1,3,3,3-hexafluoropropan-2-ol
  作者：Lennart Eberson、Michael P. Hartshorn、Finn Radner、Ola Persson

  DOI：10.1039/a705393b

  日期：——

  The reaction between aromatic compounds ArH and halogenating agents, viz. iodine chloride, chlorine, bromine, iodine, N-bromosuccinimide and N-chlorosuccinimide, in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFP) has been investigated. EPR spectroscopy established that these reagents produced persistent radical cations ArH˙+ from ArH with Erev(ArH˙+/ArH) up to 1.6, 1.3, 1.4, 1.1, 1.5 and 1.2 V vs. Ag/AgCl

  芳族化合物ArH与卤化剂之间的反应，即。研究了1,1,1,3,3,3-六氟丙烷-2-醇（HFP）中的氯化碘，氯，溴，碘，N-溴琥珀酰亚胺和N-氯琥珀酰亚胺。EPR光谱法确定，这些试剂从ArH产生持久的自由基阳离子ArH˙ +，E rev（ArH˙ + / ArH）最高可达1.6、1.3、1.4、1.1、1.5和1.2V 。Ag / AgCl。卤代物质的循环伏安法表明，在HFP中未观察到与卤离子络合的作用，这是从其显着减弱亲核反应性的能力所预期的，并且阴极峰值电势E pc（参考内部三价铁/二茂铁氧化还原对）在HFP中的含量显着或显着高于乙腈。对于N-溴代琥珀酰亚胺，其差值几乎为1V。
• Cation Radicals as Intermediates in Aromatic Halogenation with Iodine Monochloride: Solvent and Salt Effects on the Competition between Chlorination and Iodination
  作者：S. M. Hubig、W. Jung、J. K. Kochi

  DOI：10.1021/jo00100a025

  日期：1994.10

  Three distinct classes of substitutional reactivity can be discerned in the halogenation of a series of methyl-substituted methoxybenzenes (ArH) with iodine monochloride (ICl), namely, exclusive iodination, exclusive chlorination, and mixed iodination/chlorination. Spectral studies establish the prior formation of the charge-transfer complex [ArH,ICl] which suffers electron transfer to afford the reactive triad [ArH.+, I-., Cl-] according to Scheme 1. Separate reactivity studies show that chlorination and iodination can result from the quenching of the aromatic cation radical by chloride and iodine (atom), respectively. Iodination versus chlorination thus represents the competition between radical-pair and ion-pair collapse from the reactive triad, and it is predictably modulated by solvent polarity and added salt.
• A General Synthesis of Quinone Ammonium Salts
  作者：David Wiedenfeld、Mark A. Minton、David R. Glass、Vladimir N. Nesterov、Kila D. Nsamenang、Dong Han

  DOI：10.1055/s-2005-865296

  日期：——

  substituted p-dimethoxybenzenes to quinone ammonium salts. Five examples of quinone ammonium salts have been prepared with this procedure. In the first step, the aromatic species is reacted with N-(hydroxymethyl)trifluoroacetamide and trifluoroacetic acid. The trifluoroacetamide product is then oxidatively demethylated and finally hydrolyzed to afford the quinone ammonium salt.

  已经开发了将取代的对二甲氧基苯转化为醌铵盐的三步程序。用该程序制备了五个醌铵盐的例子。在第一步中，芳族物质与 N-(羟甲基)三氟乙酰胺和三氟乙酸反应。然后将三氟乙酰胺产物氧化去甲基化，最后水解得到醌铵盐。