3-morpholino-4-nitro-5-(vinylthio)thiophene-2-carbaldehyde | 1360702-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-morpholino-4-nitro-5-(vinylthio)thiophene-2-carbaldehyde
• 英文别名: 3-(4-morpholino)-4-nitro-5-(vinylsulfanyl)thiophene-2-carbaldehyde；5-Ethenylsulfanyl-3-morpholin-4-yl-4-nitrothiophene-2-carbaldehyde
• CAS: 1360702-95-9
• 化学式: C₁₁H₁₂N₂O₄S₂
• 分子量: 300.359
• InChiKey: NTMVZFSXSURUOR-UHFFFAOYSA-N

物化性质

• 沸点：
  508.4±50.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-morpholino-4-nitro-5-(vinylthio)thiophene-2-carbaldehyde 在 吗啉 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 34.0h， 生成 2-amino-7,7-dimethyl-4-(3-morpholino-4-nitro-5-(vinylthio)thien-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Chemistry of Polyhalogenated Nitrobutadienes, 12: Synthesis of Novel, Highly Substituted Bi- and Tricyclic 5,6,7,8-Tetrahydro-4H-chromen-5-ones

  摘要：

  Knoevenagel condensation of 3,4-push-pull-substituted thiophene-2-carbaldehydes 4 with malononitrile gives the gem-dicyanovinylthiophenes 5, followed by a Michael addition of dimedone and a subsequent cyclization to 4-(2-thienyl)-5,6,7,8-tetrahydro-4H-chromen-5-ones 6. Protonolysis of the latter in methanol led to a mixture of four heterocycles 7-10, the main product being the novel tricyclic 9-(2-thienyl)-6,7-dihydro-5H-thieno[3,2-b]chromen-8(9H)-one derivative 7. A mechanism of the protonolysis reaction is proposed, the structures of the two products 7a/8a have been confirmed by X-ray analysis.

  DOI：

  10.3987/com-12-s(n)108
• 作为产物：
  描述：

  2-chloro-3-morpholino-4-nitro-5-vinylsulfanylthiophene 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-morpholino-4-nitro-5-(vinylthio)thiophene-2-carbaldehyde
  参考文献：
  名称：

  Chemistry of Polyhalogenated Nitrobutadienes, 12: Synthesis of Novel, Highly Substituted Bi- and Tricyclic 5,6,7,8-Tetrahydro-4H-chromen-5-ones

  摘要：

  Knoevenagel condensation of 3,4-push-pull-substituted thiophene-2-carbaldehydes 4 with malononitrile gives the gem-dicyanovinylthiophenes 5, followed by a Michael addition of dimedone and a subsequent cyclization to 4-(2-thienyl)-5,6,7,8-tetrahydro-4H-chromen-5-ones 6. Protonolysis of the latter in methanol led to a mixture of four heterocycles 7-10, the main product being the novel tricyclic 9-(2-thienyl)-6,7-dihydro-5H-thieno[3,2-b]chromen-8(9H)-one derivative 7. A mechanism of the protonolysis reaction is proposed, the structures of the two products 7a/8a have been confirmed by X-ray analysis.

  DOI：

  10.3987/com-12-s(n)108

文献信息

• Chemistry of Polyhalogenated Nitrobutadienes, Part 11: ipso-Formylation of 2-Chlorothiophenes under Vilsmeier-Haack Conditions
  作者：Eva-Janina Vogt、Viktor A. Zapolskii、Eva Nutz、Dieter E. Kaufmann

  DOI：10.1515/znb-2012-0402

  日期：2012.4.1

  The regioselective ipso-formylation of electron-rich, 3,4-push-pull-substituted 2-chlorothiophenes under Vilsmeier-Haack conditions was performed in good yields. The synthetic scope of this new reaction was explored using various halothiophenes, chloroanilines, and 1-methyl-3-chloroindole. In comparison with their structural C-H analogs the chlorinated thiophenes, anilines, and the indole proved to be less reactive toward electrophilic attack by chloromethyleniminium salts.

  在Vilsmeier-Haack条件下，对电子丰富、3,4-推拉取代的2-氯噻吩进行了区域选择性的异位甲酰化反应，并以较好的产率获得了产物。通过使用不同的卤代噻吩、氯代苯胺和1-甲基-3-氯吲哚，探索了这一新反应的合成范围。与它们的C-H结构类似物相比，氯化的噻吩、苯胺和吲哚对氯甲基亚胺盐的亲电攻击表现出较低的活性。

• Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds
  作者：Viktor A. Zapol’skii、Ursula Bilitewski、Sören R. Kupiec、Isabell Ramming、Dieter E. Kaufmann

  DOI：10.3390/molecules25122863

  日期：——

  Substituted nitrogen heterocycles are structural key units in many important pharmaceuticals. A new synthetic approach towards heterocyclic compounds displaying antibacterial activity against Staphylococcus aureus or cytotoxic activity has been developed. The selective synthesis of a series of 64 new N-heterocycles from the three nitrobutadienes 2-nitroperchloro-1,3-butadiene, 4-bromotetrachloro-2-nitro-1

  取代的氮杂环是许多重要药物的结构关键单元。已经开发出一种新的合成方法来合成对金黄色葡萄球菌具有抗菌活性或细胞毒活性的杂环化合物。由三种硝基丁二烯 2-硝基全氯-1,3-丁二烯、4-溴四氯-2-硝基-1,3-丁二烯和 (Z)-1,1,4- 选择性合成一系列 64 个新的 N-杂环三氯-2,4-二硝基丁-1,3-二烯证明是可行的。它们与 N-、O- 和 S-亲核试剂的反应可以快速获得推挽取代的苯并恶唑啉、苯并咪唑啉、咪唑烷、噻唑烷酮、吡唑、嘧啶、吡啶并嘧啶、苯并喹啉、异噻唑、二氢异恶唑和具有独特取代模式的噻吩。检查了 64 种合成化合物的抗菌活性。此外，七种化合物（噻唑烷酮、硝基嘧啶、吲哚、吡啶并嘧啶和噻吩衍生物）表现出显着的细胞毒性，IC50 值为 1.05 至 20.1 µM。总之，证明多卤代硝基丁二烯作为各种高度官能化的药学活性杂环的结构骨架具有有趣的潜力。