ethyl 3-(toluene-p-sulphonylazo)but-2-enoate | 93953-27-6

• 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: ethyl 3-(toluene-p-sulphonylazo)but-2-enoate
• 英文别名: Ethyl 3-[(E)-(4-methylbenzene-1-sulfonyl)diazenyl]but-2-enoate；ethyl 3-[(4-methylphenyl)sulfonyldiazenyl]but-2-enoate
• CAS: 93953-27-6
• 化学式: C₁₃H₁₆N₂O₄S
• 分子量: 296.347
• InChiKey: YDJCQCSQVWWYRL-UHFFFAOYSA-N

物化性质

• 沸点：
  415.3±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酰基乙酰对氯苯胺 、 ethyl 3-(toluene-p-sulphonylazo)but-2-enoate 在 CuCl₂*2H₂O 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到4-(4-Chloro-phenylcarbamoyl)-2,5-dimethyl-1-(toluene-4-sulfonylamino)-1H-pyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Effect of Metal Ions in Organic Synthesis; Part XXV. Simple Direct Synthesis of 1-Arylsulfonylamino-3-aminocarbonylpyrroles by Reaction of Arylsulfonylazoalkenes with 3-Oxoalkanamides under Copper(II) Chloride Catalysis

  摘要：

  DOI：

  10.1055/s-1984-31006

文献信息

• Regioselective synthesis of spiro-cyclopropanated 1-aminopyrrol-2-ones by Bi(OTf)3-catalyzed one-pot ‘Mukaiyama–Michael addition/cyclization/ring-contraction’ reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes
  作者：Orazio A. Attanasi、Gianfranco Favi、Gianluca Giorgi、Fabio Mantellini、Vahuni Karapetyan、Peter Langer

  DOI：10.1016/j.tet.2009.04.018

  日期：2009.7

  Unknown spiro-cyclopropanated 1-aminopyrrol-2-ones are regioselectively prepared in high yields by Bi(OTf)3-catalyzed one-pot ‘Mukaiyama–Michael addition/cyclization/ring-contraction’ reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes at room temperature.

  未知的螺环丙烷化的1-氨基吡咯-2-酮是由Bi（OTf）3催化的1,2-双（三甲基甲硅烷氧基）单锅“ Mukaiyama–Michael加成/环化/环缩合”反应以高产率进行区域选择性制备的室温下将环丁烯与1,2-二氮杂1,3-丁二烯一起使用。
• A Novel Assembly of Substituted Pyrroles by Acid-Catalyzed Sequential Three-Component Reaction of Amines, Alkynoates, and 1,2-Diaza-1,3-dienes
  作者：Orazio A. Attanasi、Gianfranco Favi、Fabio Mantellini、Giada Moscatelli、Stefania Santeusanio

  DOI：10.1002/adsc.201100094

  日期：2011.6

  A novel protocol for the assembly of polysubstituted pyrroles has been developed through the acid‐catalyzed, sequential three‐component reaction of primary aliphatic amines, alkynoates and 1,2‐diaza‐1,3‐dienes (DDs). This methodology proceeds with complete chemo‐/regioselectivity involving first formation of an enamino ester intermediate, in situ Michael addition with azo‐ene compounds and subsequent

  通过伯脂肪族胺，炔酸和1,2-二氮杂-1,3-二烯（DDs）的酸催化顺序三组分反应，开发了一种多取代吡咯组装的新方案。该方法具有完全的化学/区域选择性，包​​括首先形成烯氨基酯中间体，与偶氮烯化合物在原位迈克尔加成，然后进行分子内闭环。
• Flexible Protocol for the Chemo- and Regioselective Building of Pyrroles and Pyrazoles by Reactions of Danishefsky’s Dienes with 1,2-Diaza-1,3-butadienes
  作者：Orazio A. Attanasi、Gianfranco Favi、Paolino Filippone、Gianluca Giorgi、Fabio Mantellini、Giada Moscatelli、Domenico Spinelli

  DOI：10.1021/ol800557h

  日期：2008.5.1

  The versatility of the Mukaiyama-Michael-type addition/heterocyclization of Danishefsky's diene with 1,2-diaza-1,3-butadienes was applied to the synthesis of both 4H-1-aminopyrroles and 4,5H-pyrazoles. Thus, the same reagents furnished different types of highly functionalized azaheterocycles essentially depending on their structure: as a matter of fact, R-1 = COOR or CONR2 differently affects the acidity of the proton at the adjacent carbon. An unexpected formation of 5H-1-aminopyrroles from the reactions carried out in water was also observed.
• Attanasi, Orazio; Perrulli, Francesca Romana; Serra-Zanetti, Franco, Heterocycles, 1985, vol. 23, # 4, p. 867 - 870
  作者：Attanasi, Orazio、Perrulli, Francesca Romana、Serra-Zanetti, Franco

  DOI：——

  日期：——