2-benzylidene-3-methyl-4-nitro-2,5-dihydrothiophene 1,1-dioxide | 53541-19-8

• 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-benzylidene-3-methyl-4-nitro-2,5-dihydrothiophene 1,1-dioxide
• 英文别名: 2-benzylidene-3-methyl-4-nitro-3,3-thiolene 1,1-dioxide；2-benzylidene-3-methyl-4-nitro-3-thiolene 1,1-dioxide；2-benzylidene-3-methyl-4-nitro-3-thiolene-1,1-dioxide；5-benzylidene-4-methyl-3-nitro-2H-thiophene 1,1-dioxide
• CAS: 53541-19-8
• 化学式: C₁₂H₁₁NO₄S
• 分子量: 265.29
• InChiKey: LCQUCNVICQKZSB-UHFFFAOYSA-N

物化性质

• 熔点：
  201-203 °C
• 沸点：
  477.8±45.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  88.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzylidene-3-methyl-4-nitro-2,5-dihydrothiophene 1,1-dioxide 在 dinitrogen tetraoxide 作用下， 以 四氯化碳 为溶剂， 反应 0.67h， 以52%的产率得到3-methyl-4,4-dinitro-2-[nitro(phenyl)methyl]-2-thiolene 1,1-dioxide
  参考文献：
  名称：

  摘要：

  A synthesis of previously unknown rigidly fixed heterocyclic structures, dinitrosulfodienes of the thiolene 1,1-dioxide series, was developed, and their structure was studied. The geometry and structural parameters of 3-methyl-4-vitro-2-[nitro(phenyl)methylene]-3-thiolene 1,1-dioxide were determined by X-ray diffraction.

  DOI：

  10.1023/a:1023415429402

文献信息

• Synthesis of bicyclic systems containing fused sulfolane and isoxazolidine rings
  作者：Valentina M. Berestovitskaya、Irina E. Efremova、Anna V. Serebryannikova、Lidiya V. Lapshina、Vladislav V. Gurzhiy

  DOI：10.1007/s10593-018-2233-y

  日期：2018.1

  hydroxylamine and N-methylhydroxylamine for the synthesis of 3-aryl-6а-methyl-6-nitrohexahydrothieno[2,3-d]isoxazole 4,4-dioxides – new representatives of original bicyclic structures combining condensed isoxazolidine and sulfolane rings. The structures of the obtained compounds were established by methods of IR spectroscopy, one-dimensional 1Н and 13С NMR spectroscopy, two-dimensional 1Н–13С HMQC and

  基于2-亚苄基-3-甲基-4-硝基-3-硫代己烯1，1-二氧化物及其取代类似物与羟胺和N-甲基羟胺的反应，开发了一种合成3-芳基-6′-甲基-的方法6-硝基六氢噻吩并[2,3- d ]异恶唑4,4-二氧化物-结合稠合的异恶唑烷和环丁砜环的原始双环结构的新代表。通过IR光谱法，一维的方法建立了所得到的化合物的结构1 Н和13 СNMR光谱，二维1 Н- 13 СHMQC和1个Н- 13个СHMBC实验，X射线结构分析。
• Synthesis of new bicyclic compounds containing fused sulfolane and pyrazolidine rings
  作者：I. E. Efremova、A. V. Serebryannikova、L. V. Lapshina、V. V. Gurzhiy、V. M. Berestovitskaya

  DOI：10.1134/s1070363216030191

  日期：2016.3

  3-Aryl-6а-methyl-6-nitro-1-carbamoylhexahydrothieno[2,3-d]pyrazole-4,4-dioxides, novel original bicyclic species consisting of fused pyrazolidine and sulfolane rings, and 1,4-adducts were obtained by reacting 2-benzylidene-3-methyl-4-nitro-3-thiolene-1,1-dioxide and its derivatives with semicarbazide.

  获得3-芳基-6α-甲基-6-硝基-1-氨基甲酰基六氢噻吩并[2,3- d ]吡唑-4,4-二氧化物，新颖的由稠合的吡唑烷和环丁砜环组成的双环物质，以及1,4-加合物使2-亚苄基-3-甲基-4-硝基-3-噻吩-1,1-二氧化物及其衍生物与氨基脲反应。
• Reactions of 2-benzylidene-3-methyl-4-nitro-2,5-dihydrothiophene 1,1-dioxide with CH acids
  作者：V. M. Berestovitskaya、M. V. Selivanova、M. I. Vakulenko、I. E. Efremova、G. A. Berkova

  DOI：10.1134/s1070428009120100

  日期：2009.12

  2-Benzylidene-3-methyl-4-nitro-2,5-dihydrothiophene 1,1-dioxide reacted with acyclic CH acids (acetylacetone, diethyl malonate, and its derivatives) according to the 1,4-addition pattern, whereas reactions of the title compound with cyclohexane-1,3-dione and 5,5-dimethylcyclohexane-1,3-dione (dimedone) were complicated by subsequent intramolecular heterocyclization leading to thieno[3,2-b]chromene

  2-苄叉基-3-甲基-4-硝基-2,5-二氢噻吩1,1-二氧化物与无环CH酸（乙酰丙酮，丙二酸二乙酯及其衍生物）按照1,4-加成模式反应，而具有环己烷-1,3-二酮和5,5-二甲基环己烷-1,3-二酮（二甲酮）的标题化合物由于随后的分子内杂环化而复杂化，从而产生噻吩并[3,2- b ]亚甲基苯衍生物。
• Reactions of aroylhydrazines with nitrosulfodienes of the 2-benzylidene-3-methyl-4-nitro-3-thiolene-1,1-dioxide series
  作者：L. V. Lapshina、A. V. Serebryannikova、I. E. Efremova、A. D. Perkhunova、S. V. Bortnikov、V. M. Berestovitskaya

  DOI：10.1134/s1070363214080131

  日期：2014.8

  Reactions of s-trans-nitrosulfodienes of the 2-benzylidene-3-methyl-4-nitro-3-thiolene-1,1-dioxide series with aroylhydrazines occur as nucleophilic 1,4-addition to give the aza-Michael adducts. Activity of the studied substrates depends on the nature of the substituents in the benzene ring of benzylidene fragment. Previously unexplored representatives of the 2-benzylidene-3-methyl-4-nitro-3-thiolene-1,1-dioxides have been synthesized.
• Synthesis of 3-aryl-6a-methyl-6-nitro-1-phenylhexahydrothieno[2,3-d]pyrazole 4,4-dioxides
  作者：Valentina M. Berestovitskaya、Irina E. Efremova、Lidiya V. Lapshina、Anna V. Serebryannikova、Vladislav V. Gurzhiy、Victoria V. Abzianidze

  DOI：10.1016/j.mencom.2015.05.010

  日期：2015.5

  Reaction of 2-benzylidene-3-methyl-4-nitro-3-thiolene 1,1-dioxides and phenylhydrazine affords 3-aryl-6a-methyl-6-nitro-1-phenylhexahydrothieno[2,3-d]pyrazole 4,4-dioxides in moderate yields.