2,3-Dimethyl-4-tosylimino-1,4-benzoquinone | 222853-23-8

• 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: 2,3-Dimethyl-4-tosylimino-1,4-benzoquinone
• 英文别名: N-(2,3-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-4-methylbenzenesulfonamide
• CAS: 222853-23-8
• 化学式: C₁₅H₁₅NO₃S
• 分子量: 289.355
• InChiKey: OENVUDLCYAEEEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-Dimethyl-4-tosylimino-1,4-benzoquinone 在 溴 作用下， 以 氯仿 为溶剂， 以81%的产率得到5,6-dibromo-2,3-dimethyl-4-tosylimino-2-cyclohexen-1-one
  参考文献：
  名称：

  Halogenation of N-substituted para-quinone monoimine and para-quinone monooxime esters: VI. Regular trends in chlorination and bromination of N-arylsulfonyl-1,4-benzoquinone monoimines alkyl-substituted in the quinoid ring

  摘要：

  Reactions of halogens with N-arylsulfonyl- 1,4-benzoquinone monoimines occur with the formation of a halogenonium ion that either transforms into a carbocation where the first halogen atom adds to the carbon in the ortho-position relative to the carbonyl carbon, or the halogenonium ion adds directly the second halogen atom.

  DOI：

  10.1134/s107042800605006x
• 作为产物：
  描述：

  在 sodium dichromate 、 溶剂黄146 作用下， 生成 2,3-Dimethyl-4-tosylimino-1,4-benzoquinone
  参考文献：
  名称：

  一些N-取代的1,4-苯醌亚胺与芳烃亚磺酸钠的反应

  摘要：

  Ñ -Arylsulfonyl，Ñ芳酰基，和Ñ - [arylsulfonylimino（苯基）甲基] -1,4-苯醌亚胺衍生物与钠arenesulfinates反应，得到1,4-，1,6-，和6,1加成产物，其根据两个并发路径形成：将芳族亚磺酸根阴离子直接亲核加成到中性醌亚胺分子上，以及将芳族亚磺酸根自由基加成至醌基亚胺衍生的自由基上的自由基离子。

  DOI：

  10.1134/s1070428014070082

文献信息

• Reaction of N-sulfonyl derivatives of 1,4-benzoquinone monoimine with substituted hydrazines
  作者：S. A. Konovalova、A. P. Avdeenko、S. A. Goncharova、V. V. D’yakonenko、S. V. Shishkina

  DOI：10.1134/s1070428016050055

  日期：2016.5

  Reaction direction of N-sulfonyl derivatives of 1,4-benzoquinone monoimine with substituted hydrazines depends on the redox potential of the quinone imine and on the basicity of the hydrazine. Aryl (alkyl)hydrazines of high basicity favor the reduction of quinone monoimine. In reactions with less basic aroylhydrazones N'-(4-oxocyclohexa-2,5-dienylidene)aroylhydrazides were obtained only from the alkylsubstituted

  1,4-苯醌单亚胺的N-磺酰基衍生物与取代的肼的反应方向取决于醌亚胺的氧化还原电势和肼的碱性。高碱性的芳基（烷基）肼有助于减少醌单亚胺。在与碱性较低的芳酰基hydr的反应中，仅从具有较低氧化还原电势的N-磺酰基衍生物的喹啉环中取代的烷基获得N ′-（4-氧代环己二-2，5-二烯基）芳酰基酰肼。
• Reaction of N-sulfonyl-1,4-benzoquinone imines with sodium azide
  作者：S. A. Konovalova、A. P. Avdeenko、S. V. Shelyazhenko、V. V. Pirozhenko、O. N. Mikhailichenko、A. L. Yusina

  DOI：10.1134/s1070428016010048

  日期：2016.1

  order of addition of the reactants, reactions of N-sulfonyl-1,4-benzoquinone imines with sodium azide afforded N-(3-azido-4-hydroxyphenyl)alkane(arene)sulfonamides, N-(3-azido-4-oxocyclohexa-2,5-dienylidene)alkane(arene)sulfonamides, and N-(3,5-diazido-4-hydroxyphenyl)-alkanesulfonamides. Quantum chemical calculations showed that the reactions begin with addition of azide ion to the quinone imine.

  取决于条件和反应物的添加顺序，N-磺酰基-1,4-苯醌亚胺与叠氮化钠的反应得到N-（3-叠氮基-4-羟基苯基）链烷烃（芳烃）磺酰胺，N-（3 -叠氮基-4-氧代环己基-2,5-二烯叉基）链烷烃（芳烃）磺酰胺和N-（3,5-二叠氮基-4-羟基苯基）链烷烃磺酰胺。量子化学计算表明，该反应开始于在醌亚胺上添加叠氮化物离子。
• Burmistrov; Burmistrova, Russian Journal of Organic Chemistry, 1998, vol. 34, # 6, p. 856 - 860
  作者：Burmistrov、Burmistrova

  DOI：——

  日期：——
• Thiocyanation of N-arylsulfonyl-, N-aroyl-, and N-[(N-arylsulfonyl)benzimidoyl]-1,4-benzoquinone imines
  作者：A. P. Avdeenko、V. V. Pirozhenko、S. A. Konovalov、D. A. Roman’kov、G. V. Palamarchuk、O. V. Shishkinc

  DOI：10.1134/s1070428009030105

  日期：2009.3

  Reactions of thiocyanate ion with N-aroyl-, N-arylsulfonyl-, and N-(N-arylsulfonylbenzimidoyl)-1,4-benzoquinone imines follow the 1,4-addition pattern, and the adducts undergo intramolecular cyclization to give the corresponding N-substituted 5-amino-1,3-benzoxathiol-2-ones as final products.
• Reaction of N-arenesulfonyl-1,4-benzoquinone imines with acetylacetone
  作者：S. A. Konovalova、A. P. Avdeenko、E. N. Lysenko、V. V. D’yakonenko、S. V. Shishkina

  DOI：10.1134/s1070428016040060

  日期：2016.4

  N-Arenesulfonyl-1,4-benzoquinone imines reacted with acetylacetone to afford different products, depending on the isolation procedure. Crystallization from polar protic solvents gave N-[4-hydroxy- 3-(2-hydroxy-4-oxopent-2-en-3-yl)phenyl]arenesulfonamides and 6-(2-oxopropyl)-4-(arenesulfonamido)phenyl acetates, whereas N-(3-acetyl-2,6-dimethyl-1-benzofuran-5-yl)arenesulfonamides were isolated by crystallization from nonpolar aprotic solvents.