N-(2-(trimethylsilyl)ethynyl)-N-(p-tosyl)but-3-yn-1-amine | 247155-40-4

• 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: N-(2-(trimethylsilyl)ethynyl)-N-(p-tosyl)but-3-yn-1-amine
• 英文别名: N-but-3-ynyl-4-methyl-N-(2-trimethylsilylethynyl)benzenesulfonamide
• CAS: 247155-40-4
• 化学式: C₁₆H₂₁NO₂SSi
• 分子量: 319.5
• InChiKey: KSRHLGNTDASHPD-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  406.9±55.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-(trimethylsilyl)ethynyl)-N-(p-tosyl)but-3-yn-1-amine 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 N-(but-3-yn-1-yl)-N-ethynyl-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Rhodium(I)-Catalyzed [2+2+2] Cycloadditions with N-Functionalized 1-Alkynylamides: A Conceptually New Strategy for the Regiospecific Synthesis of Substituted Indolines

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19990816)38:16<2426::aid-anie2426>3.0.co;2-y
• 作为产物：
  描述：

  phenyl(trimethylsilylethynyl)iodonium triflate 、 N-(but-3-yn-1-yl)-4-methylbenzenesulfonamide 在 正丁基锂 作用下， 以 甲苯 为溶剂， 以64%的产率得到N-(2-(trimethylsilyl)ethynyl)-N-(p-tosyl)but-3-yn-1-amine
  参考文献：
  名称：

  Rhodium(I)-Catalyzed [2+2+2] Cycloadditions with N-Functionalized 1-Alkynylamides: A Conceptually New Strategy for the Regiospecific Synthesis of Substituted Indolines

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19990816)38:16<2426::aid-anie2426>3.0.co;2-y

文献信息

• Synthesis of Aminopyridines and Aminopyridones by Cobalt-Catalyzed [2+2+2] Cycloadditions Involving Yne-Ynamides: Scope, Limitations, and Mechanistic Insights
  作者：Pierre Garcia、Yannick Evanno、Pascal George、Mireille Sevrin、Gino Ricci、Max Malacria、Corinne Aubert、Vincent Gandon

  DOI：10.1002/chem.201103906

  日期：2012.4.2

  switched toward 3‐ or 4‐aminopyridines. Application of this synthetic methodology to the construction of the aminopyridone framework using a yne‐ynamide and an isocyanate was also briefly examined. DFT computations suggest that 3‐aminopyridines are formed by formal [4+2] cycloaddition between the nitrile and the intermediate cobaltacyclopentadiene, whereas 4‐aminopyridines arise from an insertion pathway

  深入研究了乙炔酰胺和腈之间钴催化的[2 + 2 + 2]环加成反应以提供氨基吡啶。已评估了约30个具有广泛空间需求和电子特性的腈，其中一些为金属催化的芳烃形成开辟了新的前景。特别是，使用[CpCo（CO）（dmfu）]（dmfu =富马酸二甲酯）作为预催化剂可以将缺电子的腈掺入吡啶核中。修饰炔炔基上的取代基使区域选择性转向3或4氨基吡啶。还简要研究了这种合成方法在使用炔属酰胺和异氰酸酯构建氨基吡啶酮骨架中的应用。
• Silver-Catalyzed Cycloisomerization of 1,n-Allenynamides
  作者：Pierre Garcia、Youssef Harrak、Lisa Diab、Pierre Cordier、Cyril Ollivier、Vincent Gandon、Max Malacria、Louis Fensterbank、Corinne Aubert

  DOI：10.1021/ol201041h

  日期：2011.6.3

  A variety of allenynamides can undergo cycloisomerization reactions in the presence of silver triflate thus leading to the formation of N-containing heterocycles incorporating cross-conjugated trienes. Access to new dienic 4-piperidinone and azepane motifs was achieved. An extension to one-pot tandem sequences involving silver-catalyzed cycloisomerization/Diels Alder reaction was also examined.
• A Highly Efficient and Flexible Synthesis of Substituted Carbazoles by Rhodium-Catalyzed Inter- and Intramolecular Alkyne Cyclotrimerizations
  作者：Bernhard Witulski、Carole Alayrac

  DOI：10.1002/1521-3773(20020902)41:17<3281::aid-anie3281>3.0.co;2-g

  日期：2002.9.2
• Regioselective Cobalt-Catalyzed Formation of Bicyclic 3- and 4-Aminopyridines
  作者：Pierre Garcia、Yannick Evanno、Pascal George、Mireille Sevrin、Gino Ricci、Max Malacria、Corinne Aubert、Vincent Gandon

  DOI：10.1021/ol200417p

  日期：2011.4.15

  Bimolecular cobalt-catalyzed [2 + 2 + 2] cycloadditions between yne-ynamides and nitriles afford bicyclic 3- or 4-aminopyridines in up to 100% yield. The high regioselectivity observed depends on the substitution pattern at the starting ynamide. Aminopyridines bearing TMS and Ts groups are efficiently deprotected in an orthogonal fashion.