3-(苯磺酰基)-4-硝基噻吩 | 62256-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3-(苯磺酰基)-4-硝基噻吩
• 英文名称: 3-nitro-4-(phenylsulfonyl)thiophene
• 英文别名: Thiophene, 3-nitro-4-(phenylsulfonyl)-；3-(benzenesulfonyl)-4-nitrothiophene
• CAS: 62256-06-8
• 化学式: C₁₀H₇NO₄S₂
• 分子量: 269.302
• InChiKey: AQRJSIWEYPIRHR-UHFFFAOYSA-N

物化性质

• 沸点：
  490.1±30.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(苯磺酰基)-4-硝基噻吩 在 silver nitrate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 19.25h， 生成 (E,E)-1-(4-methylphenyl)-4-methylsulfonyl-2-nitro-3-phenylsulfonyl-1,3-butadiene
  参考文献：
  名称：

  通过3-硝基-4-（苯磺酰基）噻吩的初始开环获得稠合的均芳和杂芳族衍生物。

  摘要：

  在整个开环/成环方案中，（E，E）-4-甲硫基-2-硝基-3-苯基磺酰基-1-吡咯烷酮-1,3-丁二烯（7）[源自于具有吡咯烷和硝酸银的EtOH中的3-硝基-4-（苯基磺酰基）噻吩（6）是环稠合的芳族（萘，菲）或杂芳族（苯并噻吩）化合物的硝基（苯基磺酰基）衍生物的极佳前体用常规方法不易实现其取代模式。（E，E）-1-芳基-4-甲基磺酰基-2-硝基-3-苯基磺酰基-1,3-丁二烯（9）的热电重排是关键步骤，这要归功于适当的几何和电子因素，发生在前所未有的温和条件下，随后发生不可逆转的变化，

  DOI：

  10.1021/jo034264q

文献信息

• Ring-Opening/Ring-Closing Protocols from Nitrothiophenes: Easy Access to<i>N</i>-Fused Pyrroles through a Tandem 1,6-H Shift/6π-Electrocyclization
  作者：Lara Bianchi、Massimo Maccagno、Giovanni Petrillo、Carlo Scapolla、Cinzia Tavani、Alessandra Tirocco

  DOI：10.1002/ejoc.201301236

  日期：2014.1

  amines and proper modification of the resulting 1,3-diene enables a simple and versatile approach to N-fused pyrroles of both synthetic and biological interest through 1,6-H shift followed by 6π 1,5-electrocyclization. This protocol is effectively driven to the isolated pyrroles by an easy aromatization.

  3-硝基-4-（苯磺酰基）噻吩与胺的开环和所得 1,3-二烯的适当修饰使得通过 1,6-H 获得具有合成和生物学意义的 N-稠合吡咯的简单而通用的方法移位，然后是 6π 1,5-电环化。该协议通过简单的芳构化有效地驱动到分离的吡咯。
• Sequential Annulations to Interesting Novel Pyrrolo[3,2-c]carbazoles
  作者：Alice Benzi、Lara Bianchi、Massimo Maccagno、Angela Pagano、Giovanni Petrillo、Cinzia Tavani

  DOI：10.3390/molecules24203802

  日期：——

  pyrrole benzannulation methodology that, employing versatile nitrodienes from our lab as useful C4 building blocks, led to indole derivatives characterized by unusual patterns of substitution. The 6-nitro-7-arylindoles resulting from suitably derivatized, non-symmetric dienes are of foreseeable synthetic interest in search for new polyheterocyclic systems. As an example, pyrrolocarbazoles with a rarely

  在此，我们报告了最近实施的吡咯苯并环化方法的重要而有价值的扩展，该方法使用我们实验室中的多功能硝基二烯作为有用的 C4 构建单元，导致以不寻常的取代模式为特征的吲哚衍生物。由适当衍生的非对称二烯产生的 6-硝基-7-芳基吲哚在寻找新的多杂环系统方面具有可预见的合成兴趣。例如，具有很少报道的环融合的吡咯并咔唑是用经典的 Cadogan 协议合成的。此外，已证明硝基易于还原为胺肯定会为进一步有趣的阐述开辟道路。
• Nitro-substituted tetrahydroindolizines and homologs: Design, kinetics, and mechanism of α-glucosidase inhibition
  作者：Cinzia Tavani、Lara Bianchi、Annalisa De Palma、Giovanna Ilaria Passeri、Giuseppe Punzi、Ciro Leonardo Pierri、Angelo Lovece、Maria Maddalena Cavalluzzi、Carlo Franchini、Giovanni Lentini、Giovanni Petrillo

  DOI：10.1016/j.bmcl.2017.07.068

  日期：2017.9

  A series of 1-[(methylsulfonyl)methyl]-2-nitro-5,6,7,8-tetrahydroindolizines and homologs were designed, prepared, and evaluated as non-sugar-type a-glucosidase inhibitors. The inhibitory activity appeared to be related to cyclo homologation with the best congeners being tetrahydroindolizines. The introduction of a methoxycarbonyl group as an additional hydrogen bond acceptor into the exocyclic methylene group was beneficial affording the most potent congener 3e (half maximal inhibitory concentration, IC50 = 8.0 +/- 0.1 mu M) which displayed 25-fold higher inhibitory activity than 1-deoxynojirimycin (2, IC50 = 203 +/- 9 mu M)-the reference compound. Kinetic analysis indicated that compound 3e is a mixed inhibitor with preference for the free enzyme over the alpha-glucosidase-substrate complex (K-i,K-free = 3.6 mu M; K-i,K-bound = 7.6 mu M). Molecular docking experiments were in agreement with kinetic results indicating reliable interactions with both the catalytic cleft and other sites. Circular dichroism spectroscopy studies suggested that the inhibition exerted by 3e may involve changes in the secondary structure of the enzyme. Considering the relatively low molecular weight of 3e together with its high fraction of sp(3) hybridized carbon atoms, this nitro-substituted tetrahydroindolizine may be considered as a good starting point towards new leads in the area of alpha-glucosidase inhibitors. (C) 2017 Elsevier Ltd. All rights reserved.
• Access to Ring-Fused Homo- and Heteroaromatic Derivatives via an Initial Ring-Opening of 3-Nitro-4-(phenylsulfonyl)thiophene¹
  作者：Lara Bianchi、Carlo Dell'Erba、Massimo Maccagno、Angelo Mugnoli、Marino Novi、Giovanni Petrillo、Fernando Sancassan、Cinzia Tavani

  DOI：10.1021/jo034264q

  日期：2003.6.1

  in EtOH] is revealed to be an excellent precursor of nitro(phenylsulfonyl) derivatives of ring-fused aromatic (naphthalene, phenanthrene) or heteroaromatic (benzothiophene) compounds whose substitution pattern cannot be easily achieved by conventional methods. The key step is represented by a thermal electrocyclic rearrangement of (E,E)-1-aryl-4-methylsulfonyl-2-nitro-3-phenylsulfonyl-1,3-butadienes

  在整个开环/成环方案中，（E，E）-4-甲硫基-2-硝基-3-苯基磺酰基-1-吡咯烷酮-1,3-丁二烯（7）[源自于具有吡咯烷和硝酸银的EtOH中的3-硝基-4-（苯基磺酰基）噻吩（6）是环稠合的芳族（萘，菲）或杂芳族（苯并噻吩）化合物的硝基（苯基磺酰基）衍生物的极佳前体用常规方法不易实现其取代模式。（E，E）-1-芳基-4-甲基磺酰基-2-硝基-3-苯基磺酰基-1,3-丁二烯（9）的热电重排是关键步骤，这要归功于适当的几何和电子因素，发生在前所未有的温和条件下，随后发生不可逆转的变化，