N-phenylsulfonyl-2-methyl-1,4-benzoquinone imine | 73021-86-0

• 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-phenylsulfonyl-2-methyl-1,4-benzoquinone imine
• 英文别名: N-(3-methyl-4-oxo-cyclohexa-2,5-dienylidene)-benzenesulfonamide；N-(3-Methyl-4-oxo-cyclohexa-2,5-dienyliden)-benzolsulfonamid；2-Methyl-4-N-benzolsulfonylchinonimin；N-(3-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)benzenesulfonamide
• CAS: 73021-86-0
• 化学式: C₁₃H₁₁NO₃S
• 分子量: 261.301
• InChiKey: SXPMXTBXODGYBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  N-phenylsulfonyl-2-methyl-1,4-benzoquinone imine 在 盐酸 作用下， 以 氯仿 为溶剂， 以96%的产率得到N-phenylsulfonyl-6-chloro-2-methyl-4-aminophenol
  参考文献：
  名称：

  Halogenation of N-substituted p-quinone imines and p-quinone oxime esters: IV. Chlorination and bromination of N-arylsulfonyl-2(3)-methyl(2-chloro)-1,4-benzoquinone monoimines

  摘要：

  The addition of halogens to N-arylsulfonyl-1,4-benzoquinone imines, which exist in a solution as Z and E isomers, is controlled by the steric factor. Z-E Isomerization strongly affects the stability of cyclohexene structures formed by halogenation of 1,4-benzoquinone imines. The halogenation of N-arylsulfonyl-1,4-benzoquinone imines was found to be accompanied by prototropic rearrangement.

  DOI：

  10.1134/s1070428006030031
• 作为产物：
  描述：

  苯磺酰氯 在 吡啶 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.5h， 生成 N-phenylsulfonyl-2-methyl-1,4-benzoquinone imine
  参考文献：
  名称：

  Synthesis of 5-substituted 2,3-dihydrobenzofurans in a one-pot oxidation/cyclization reaction

  摘要：

  Variously substituted 2,3-dihydrobenzofurans have been synthesized according :o a sequential one-pot oxidation/cyclization procedure between para-aminophenol derivatives and an azadiene. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.020

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。
• Reactions of N-arylsulfonylquinone imines with enamines
  作者：A. P. Avdeenko、S. A. Konovalova、O. N. Mikhailichenko、A. L. Yusina、A. A. Santalova、G. V. Palamarchyk、R. I. Zubatyuk、O. V. Shishkin、K. S. Burmistrov

  DOI：10.1134/s1070428011080094

  日期：2011.8

  Depending on the reaction conditions N-arylsulfonyl-1,4-quinone imines with enamines led to the formation of the products of 1,4-addition, derivatives of benzo- and naphthofuran, indole, and benzindole.
• Quinone Imides. IV. p-Quinone Monosulfonimides
  作者：Roger Adams、J. H. Looker

  DOI：10.1021/ja01147a078

  日期：1951.3
• ——
  作者：A. P. Avdeenko、I. L. Marchenko、S. A. Konovalova

  DOI：10.1023/a:1016555324390

  日期：——

  The study of chlorination of N-(N-arylsulfonylarylimidoyl)-1,4-benzoquinone imines and of N-(N-arylsulfonylarylimidoyl)-1,4-aminophenols revealed that the dominant stage in the process was the formation of cyclohexene structures, 4-(N-arylsulfonylarylimidoyl)imino-2,5,6-trichloro-2-cyclohexene-1-ones, resulting from addition of a Cl-2 molecule across the C=C bond of the quinoid ring. These substances suffer a prototropic rearrangements yielding N-(N-arylsulfonylarylimidoyl)-2,3,6-trichloro-4-aminophenols. The latter are the most common reaction products. The products of deeper chlorination were also obtained.
• 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.