1-Tosyl-6-(4-(trifluoromethyl)phenyl)-8-(trimethylsilyl)-1,2,3,4-tetrahydro-1,7-naphthyridine | 1282040-18-9

• 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: 1-Tosyl-6-(4-(trifluoromethyl)phenyl)-8-(trimethylsilyl)-1,2,3,4-tetrahydro-1,7-naphthyridine
• 英文别名: trimethyl-[1-(4-methylphenyl)sulfonyl-6-[4-(trifluoromethyl)phenyl]-3,4-dihydro-2H-1,7-naphthyridin-8-yl]silane
• CAS: 1282040-18-9
• 化学式: C₂₅H₂₇F₃N₂O₂SSi
• 分子量: 504.648
• InChiKey: XEVHRSMUYNVRQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-Tosyl-6-(4-(trifluoromethyl)phenyl)-8-(trimethylsilyl)-1,2,3,4-tetrahydro-1,7-naphthyridine 在 硫酸 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 6-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydro-1,7-naphthyridine
  参考文献：
  名称：

  Regioselective Cobalt-Catalyzed Formation of Bicyclic 3- and 4-Aminopyridines

  摘要：

  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.

  DOI：

  10.1021/ol200417p
• 作为产物：
  描述：

  pent-4-yn-1-yl methanesulfonate 在 iron(III) chloride hexahydrate 、 [Co(Cp)(CO)(dimethyl fumarate)] 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 15.0h， 生成 1-Tosyl-6-(4-(trifluoromethyl)phenyl)-8-(trimethylsilyl)-1,2,3,4-tetrahydro-1,7-naphthyridine
  参考文献：
  名称：

  Regioselective Cobalt-Catalyzed Formation of Bicyclic 3- and 4-Aminopyridines

  摘要：

  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.

  DOI：

  10.1021/ol200417p

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。
• 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.