3,5-dimethyl-N-phenylsulfonyl-1,4-benzoquinonimine | 216066-10-3

• 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: 3,5-dimethyl-N-phenylsulfonyl-1,4-benzoquinonimine
• 英文别名: N-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)benzenesulfonamide
• CAS: 216066-10-3
• 化学式: C₁₄H₁₃NO₃S
• mdl: MFCD00532938
• 分子量: 275.328
• InChiKey: KRIZULSDJWTLNC-UHFFFAOYSA-N

物化性质

• 沸点：
  428.2±48.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 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：
  72
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-N-phenylsulfonyl-1,4-benzoquinonimine 在 盐酸 作用下， 以 氯仿 为溶剂， 生成 N-(3-Chloro-4-hydroxy-2,6-dimethyl-phenyl)-benzenesulfonamide
  参考文献：
  名称：

  Avdeenko; Menafova; Zhukova, Russian Journal of Organic Chemistry, 1998, vol. 34, # 2, p. 210 - 220

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲基-4-氨基苯酚 在 lead(IV) acetate 、 水 、 碳酸氢钠 、 溶剂黄146 作用下， 生成 3,5-dimethyl-N-phenylsulfonyl-1,4-benzoquinonimine
  参考文献：
  名称：

  Avdeenko; Menafova; Zhukova, Russian Journal of Organic Chemistry, 1998, vol. 34, # 2, p. 210 - 220

  摘要：

  DOI：

文献信息

• Reaction of N-sulfonyl-1,4-benzoquinone imines with enamines
  作者：S. A. Konovalova、A. P. Avdeenko、V. V. Pirozhenko、A. L. Yusina、G. V. Palamarchuk、S. V. Shishkina

  DOI：10.1134/s1070428017040054

  日期：2017.4

  4-benzoquinone imine reacted with enamines to give 1,4-addition products and products of their subsequent cyclization, substituted 5-aminobenzofurans and 5-aminoindoles, depending on the solvent nature, electron-withdrawing power of the substituent on the quinone imine nitrogen atom, and enamine structure. The presence of strong electron-withdrawing trifluoromethanesulfonyl group on the quinone imine nitrogen

  1,4-苯醌亚胺的N-磺酰基衍生物与烯胺反应，生成1,4-加成产物及其后续环化产物，取代的5-氨基苯并呋喃和5-氨基吲哚，这取决于溶剂的性质，吸电子能力。醌亚胺氮原子上的取代基和烯胺结构。醌亚胺氮原子上存在强吸电子三氟甲磺酰基，有助于形成1,4-加成产物和苯并呋喃衍生物。
• 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。
• Activated sterically strained C=N bond in N-substituted p-quinone mono- and diimines: XIII. Reactions of N-alkyl(aryl, trifluoromethyl)sulfonyl-, N-arylsulfinyl- and N-arylsulfanyl-1,4-benzoquinone monoimines with alcohols
  作者：A. P. Avdeenko、S. A. Konovalova、O. N. Mikhailichenko、A. A. Santalova、G. V. Palamarchuk、O. V. Shishkin

  DOI：10.1134/s107042801205003x

  日期：2012.5

  Steric strains arising between the substituent atoms at nitrogen (S, SO, or SO2) and the methyl group located in positions 3 or 5 of the quinoid ring of 3,5-dimethyl-substituted quinone monoimines lead to the increased angle C=N-S. As a result in these quinone monoimines the reactions of 1,2-addition become thermodynamically possible since the formation of quinolide structures with the sp(3)-hybridized carbon atom removes the steric strain.
• Avdeenko, Russian Journal of Organic Chemistry, 2000, vol. 36, # 4, p. 522 - 527
  作者：Avdeenko

  DOI：——

  日期：——
• Halogenation of N-substituted para-quinone monoimine and para-quinone monooxime esters: V. Chlorination and bromination of N-arylsulfonyl-1,4-benzoquinone monoimines dialkyl-substituted in the quinoid ring
  作者：A. P. Avdeenko、S. A. Konovalova

  DOI：10.1134/s1070428006050058

  日期：2006.5

  The direction of halogen addition to N-arylsulfonyl-1,4-benzoquinone monoimines dialkyl-substituted in the quinoid ring is governed by the steric factors: the size and position of the substituent, the halogen volume, and the position of the substituent at the nitrogen. The first stage of halogenation of N-arylsulfonyl-4-aminophenols with two alkyl substituents in the phenylsulfonyl ring largely occurs as electrophilic substitution.