N-(3-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)-methanesulfonamide | 321961-54-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-(3-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)-methanesulfonamide
• 英文别名: N-(3-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)methanesulfonamide
• CAS: 321961-54-0
• 化学式: C₈H₉NO₃S
• 分子量: 199.23
• InChiKey: WPWNWCUXHHOYHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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-(3-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)-methanesulfonamide 、 3-氨基巴豆酸乙酯 以 氯仿 为溶剂， 以74%的产率得到ethyl 3-amino-2-{2-hydroxy-5-[(methanesulfonyl)amino]-3-methylphenyl}but-2-enoate
  参考文献：
  名称：

  N-磺酰基-1,4-苯醌亚胺与烯胺的反应

  摘要：

  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。

  DOI：

  10.1134/s1070428017040054

文献信息

• Annulation of enaminones with quinonediimides/quinoneimides for selective synthesis of indoles and 2-aminobenzofurans
  作者：Zukang Zhong、Lihua Liao、Yunyun Liu、Ming Zhang、Jie-Ping Wan

  DOI：10.1039/d3cc01687k

  日期：——

  The annulation reactions of enaminones with quinonediimides/quinoneimides for the selective synthesis of indoles and 2-aminobenzofurans have been realized. With Zn(II) catalysis, quinonediimides reacted with enaminones to give indoles via HNMe2-elimination-based aromatization. With Fe(III) catalysis, the reactions of quinoneimides with enaminones provided 2-aminobenzofurans via a key dehydrogenative

  实现了烯胺酮与醌二亚胺/醌亚胺的环化反应选择性合成吲哚和 2-氨基苯并呋喃。在 Zn( II ) 催化下，醌二亚胺与烯胺酮反应，通过基于HNMe 2消除的芳构化反应生成吲哚。在 Fe( III ) 催化下，醌亚胺与烯胺酮的反应通过关键的脱氢芳构化反应提供 2-氨基苯并呋喃。
• Reactions of N-aryl(methyl, trifluoromethyl)sulfonyl-1,4-benzoquinone monoimines with sodium sulfinates
  作者：A. P. Avdeenko、S. A. Konovalova、O. N. Mikhailichenko、S. V. Shelyazhenko、V. V. Pirozhenko、L. M. Yagupol’skii

  DOI：10.1134/s107042801202011x

  日期：2012.2

  In reactions with sodium sulfinates of N-substituted 1,4-benzoquinone monoimines with the quinoid ring having free positions 2 and/or 6 the fraction of products of 1,4-addition of the sulfinate ion grows in the series ArSO2 -> MeSO2 -> CF3SO2. In the case of 2,6-dimethyl derivatives the 1,6-addition is preferable, and the amount of products of 6,1-addition decreases.
• Synthesis and thiocyanation of N-alkyl(trifluoromethyl)sulfonyl 1,4-benzoquinone monoimines
  作者：A. P. Avdeenko、S. A. Konovalova、O. N. Mikhailichenko、S. V. Shelyazhenko、V. V. Pirozhenko、L. M. Yagupol’skii

  DOI：10.1134/s1070428011040075

  日期：2011.4

  New N-alkyl(trifluoromethyl)sulfonyl 1,4-benzoquinone monoimines were synthesized, and their thiocyanation gave 5-alkyl(trifluoromethyl)sulfonylamino-1,3-benzoxathiol-2-ones. An intermediate thiocyanation product, 5-trifluoromethylsulfonylamino-1,3-benzoxathiol-2-imine, was isolated for the first time.
• 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。