N-(2,6-dimethylphenyl)-5-chloro-2-nitrosoaniline | 1264688-46-1

• 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: N-(2,6-dimethylphenyl)-5-chloro-2-nitrosoaniline
• 英文别名: N-(5-chloro-2-nitrosophenyl)-2,6-dimethylaniline
• CAS: 1264688-46-1
• 化学式: C₁₄H₁₃ClN₂O
• 分子量: 260.723
• InChiKey: LYAQZQBUHYTJSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,6-dimethylphenyl)-5-chloro-2-nitrosoaniline 以 二氯甲烷 、 乙腈 为溶剂， 生成 N-butyl-6-chloro-1-(2,6-dimethylphenyl)benzimidazol-2-amine
  参考文献：
  名称：

  Simple Synthesis of 2-Aminoaryliminophosphoranes from N-Aryl-2-nitroso­anilines and Their Application in 2-Aminobenzimidazole Synthesis

  摘要：

  Condensation of N-aryl-2-nitrosoanilines with triphenylphosphine leads efficiently to substituted aryliminophosphoranes which, in turn, react with alkyl isocyanates furnishing 2-alkylaminobenzimidazole derivatives in high yields.

  DOI：

  10.1055/s-0033-1340055
• 作为产物：
  描述：

  对硝基氯苯 、 2,6-二甲基苯胺 在 potassium tert-butylate 、 盐酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 水 为溶剂， 以84%的产率得到N-(2,6-dimethylphenyl)-5-chloro-2-nitrosoaniline
  参考文献：
  名称：

  Simple Synthesis of N-Aryl-2-nitrosoanilines in the Reaction of Nitroarenes with Aniline Anion Derivatives

  摘要：

  由伯芳香胺生成的阴离子与取代硝基苯反应，形成σH加合物，在碱性反应条件下，这些加合物转化为N-芳基-2-亚硝基胺。在某些情况下观察到的硝基芳烃中反应性卤素的竞争性取代可以通过选择的溶剂来控制。

  DOI：

  10.1055/s-0030-1258230

文献信息

• Efficient Synthesis of 1-Arylquinoxalin-2(1<i>H</i>)-ones<i>via</i>Cyclocondensation of<i>N</i>-Aryl-Substituted 2-Nitrosoanilines with Functionalized Alkyl Acetates
  作者：Zbigniew Wróbel、Karolina Stachowska、Andrzej Kwast、Agata Gościk、Magdalena Królikiewicz、Robert Pawłowski、Izabela Turska

  DOI：10.1002/hlca.201200304

  日期：2013.5

  N‐Aryl‐substituted 2‐nitrosoanilines (=2‐nitrosobenzenamines) 1, readily available by nucleophilic substitution of the ortho‐H‐atom in nitroarenes with arenamines, react with 2‐substituted acetic acid esters in the presence of a weak base giving 1‐arylquinoxalin‐2(1H)‐ones (Scheme 2). This cyclocondensation allows for the synthesis of compounds 2–4, unsubstituted at C(3) or substituted by alkyl, aryl

  N-芳基取代的2-亚硝基苯胺（= 2-亚硝基苯甲胺）1可通过芳烃将硝基芳烃中的邻-H-原子进行亲核取代而容易获得，可在弱碱存在下与2-取代的乙酸酯反应，得到1 -芳基喹喔啉-2（1 H）-1 （方案2）。此环化缩合允许化合物的合成2 - 4，在C（3）未取代的或者被烷基，芳基，酯，酰胺，和酮基取代的，以良好至优异的产率（表1 - 4）。
• A Two-Step Synthesis of Selected 1,2,3,4-Tetrahydroquinoxaline Derivatives from N-Aryl-2-nitrosoanilines and Arylidenecyanoacetic Esters
  作者：Zbigniew Wróbel、Magdalena Królikiewicz、Kacper Błaziak、Witold Danikiewicz

  DOI：10.1055/s-0033-1339467

  日期：——

  Reaction of N-aryl-2-nitrosoanilines with alkyl aryl­idenecyanoacetates in the presence of Et3N in MeCN leads to substituted 1,2,3,4-tetrahydroquinoxaline derivatives in reasonable yields. The reaction comprises nucleophilic addition of the nitrosoaniline to the Michael acceptor followed by cyclization involving the nitroso group. Since the reactive nitrogen groups in N-aryl-2-­nitrosoanilines are

  N-芳基-2-亚硝基苯胺与亚芳基氰基乙酸烷基酯在 Et3N 存在下在 MeCN 中反应以合理的产率生成取代的 1,2,3,4-四氢喹喔啉衍生物。该反应包括亚硝基苯胺与迈克尔受体的亲核加成，然后是涉及亚硝基的环化。由于 N-芳基-2-亚硝基苯胺中的活性氮基团具有相反的特性，该反应具有区域选择性，此外还发现它具有非对映选择性。
• Simple Synthesis of Quinoxalin-2(1<i>H</i>)-one<i>N</i>-Oxides from<i>N</i>-Aryl-2-nitrosoanilines and Alkylated Cyanoacetic Esters
  作者：Magdalena Królikiewicz、Zbigniew Wróbel

  DOI：10.1002/jhet.1947

  日期：2014.1

  N‐Aryl‐2‐nitrosoanilines, available from the reaction of N‐arylamines with nitroarenes, condense under alkaline conditions with alkylated derivatives of cyanoacetic esters furnishing quinoxalin‐2(1H)‐one N‐oxides in good to excellent yields. The reaction involves the condensation of the carbanion with the nitroso group leading to the nitrone intermediate, followed by intramolecular acylation of the

  N-芳基-2-亚硝基苯胺可从N-芳基胺与硝基芳烃的反应中获得，在碱性条件下与氰基乙酸酯的烷基化衍生物缩合，可提供喹喔啉-2（1H）-一N-氧化物，收率良好至优异。该反应涉及碳负离子与亚硝基的缩合，生成硝酮中间体，然后分子内将胺官能团酰化。
• A Short Preparation of Pyrroloquinoxalinones via a Cascade Reaction of N-Aryl-5-alkylamino-2-nitrosoanilines with Methyl 2-Cyanoalkanoates: Unexpected Direction of Nucleophilic Substitution of Hydrogen
  作者：Zbigniew Wróbel、Magdalena Królikiewicz、Piotr Cmoch

  DOI：10.1055/s-0032-1316903

  日期：——

  N-Aryl-2-nitrosoanilines possessing 5-alkylamino groups undergo a bisheteroannulation reaction with anions of 2-cyanoalkanecarboxylates resulting in pyrroloquinoxalinone derivatives. The cascade reaction involves condensation of the cyanoester anions with the nitroso group, unusual nucleophilic substitution of hydrogen in the nitrosoaniline-derived intermediate with the second carbanion molecule, and double intramolecular acylation of the amino functions.
• Synthesis of 2-Alkylidene-3-acylquinoxalines from N-Aryl-2-nitrosoanilines and 1,3-Diketones
  作者：Zbigniew Wróbel、Adam Trawczyński

  DOI：10.1055/s-0034-1379238

  日期：——

  In the reaction of N-aryl-2-nitrosoanilines with -diketones, a condensation of the nitroso group with diketone carbanion followed by condensation of the amino function with the less crowded carbonyl group leads to 2-alkylidene-3-acyl-1,2-dihydroquinoxalines under mild basic conditions.