1-(methylsulfonyl)-3-(thiophen-3-yl)-1,2-dihydroquinoline | 1345091-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(methylsulfonyl)-3-(thiophen-3-yl)-1,2-dihydroquinoline
• 英文别名: 1-methylsulfonyl-3-thiophen-3-yl-2H-quinoline
• CAS: 1345091-50-0
• 化学式: C₁₄H₁₃NO₂S₂
• 分子量: 291.395
• InChiKey: PZMSHBZDDPJYBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(methylsulfonyl)-3-(thiophen-3-yl)-1,2-dihydroquinoline 在 potassium tert-butylate 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以93%的产率得到3-(3-噻吩基)喹啉
  参考文献：
  名称：

  Metal–Ligand Binding Interactions in Rhodium/Palladium-Catalyzed Synthesis of Dihydroquinolines

  摘要：

  A domino Rh- and Pd-catalyzed synthesis of dihydroquinolines is disclosed. Two metals and two ligands are placed in one reaction vessel along with the two reactive reagents to afford selective sequential coupling despite the potential for side reactions. In this report, we describe mechanistic investigations attempting to discern the catalystligand interactions occurring in this domino reaction. Through these studies, the reactivity and relative catalyst ligand loadings were successfully tuned to efficiently access the heterocyclic products.

  DOI：

  10.1021/jo502074s
• 作为产物：
  描述：

  1-氯-2-碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 hydroxo(1,5-cyclooctadiene)rhodium (I) dimer 、 palladium diacetate 、 potassium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 20.0h， 生成 1-(methylsulfonyl)-3-(thiophen-3-yl)-1,2-dihydroquinoline
  参考文献：
  名称：

  多米诺骨牌铑催化的炔基化/钯催化的氮基化：机理研究

  摘要：

  探戈需要两个步骤：实现了多氢喹啉的多米诺骨牌多催化合成，其中铑催化的炔烃芳基化产物通过钯促进的CN交叉偶联而环化（参见方案）。催化剂与潜在可交换配体的组合非常引人注目，因为每种金属-配体组合均可提供特定的反应性和选择性。

  DOI：

  10.1002/anie.201103692

文献信息

• Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: A Mechanistic Investigation
  作者：Jane Panteleev、Lei Zhang、Mark Lautens

  DOI：10.1002/anie.201103692

  日期：2011.9.19

  It takes two to tango: A domino multicatalytic synthesis of dihydroquinolines is realized, wherein the products of a rhodium‐catalyzed arylation of alkynes are cyclized by a palladium‐promoted CN cross‐coupling (see scheme). The combination of catalysts with potentially exchangeable ligands is remarkable as each metal–ligand combination affords specific reactivity and selectivity.

  探戈需要两个步骤：实现了多氢喹啉的多米诺骨牌多催化合成，其中铑催化的炔烃芳基化产物通过钯促进的CN交叉偶联而环化（参见方案）。催化剂与潜在可交换配体的组合非常引人注目，因为每种金属-配体组合均可提供特定的反应性和选择性。
• Metal–Ligand Binding Interactions in Rhodium/Palladium-Catalyzed Synthesis of Dihydroquinolines
  作者：Lei Zhang、Jane Panteleev、Mark Lautens

  DOI：10.1021/jo502074s

  日期：2014.12.19

  A domino Rh- and Pd-catalyzed synthesis of dihydroquinolines is disclosed. Two metals and two ligands are placed in one reaction vessel along with the two reactive reagents to afford selective sequential coupling despite the potential for side reactions. In this report, we describe mechanistic investigations attempting to discern the catalystligand interactions occurring in this domino reaction. Through these studies, the reactivity and relative catalyst ligand loadings were successfully tuned to efficiently access the heterocyclic products.