N-(3-(2-chlorophenyl)prop-2-yn-1-yl)-4-methylbenzenesulfonamide | 1364319-35-6

• 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: N-(3-(2-chlorophenyl)prop-2-yn-1-yl)-4-methylbenzenesulfonamide
• 英文别名: N-[3-(2-chlorophenyl)prop-2-ynyl]-4-methylbenzenesulfonamide
• CAS: 1364319-35-6
• 化学式: C₁₆H₁₄ClNO₂S
• 分子量: 319.812
• InChiKey: BGCCZMKJRJSJQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-(2-chlorophenyl)prop-2-yn-1-yl)-4-methylbenzenesulfonamide 在 [Rh(OH)(cod)]2 、 palladium diacetate 、 potassium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 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 为溶剂， 反应 19.0h， 生成 3-phenyl-1-tosyl-1,2-dihydroquinoline
  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：

  对甲苯磺酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 N-(3-(2-chlorophenyl)prop-2-yn-1-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  N-炔丙基亚胺与具有两种不同化学选择性的蒽基的金催化环

  摘要：

  金催化的N-炔丙基乙酰胺与蒽的环化反应可以通过两种不同的机理进行。在末端N-炔丙基炔基酰胺的情况下，其生成的α-亚氨基金卡宾与链状炔反应生成乙烯基阳离子以实现水解，经p处理后最终生成吡咯并[2,3- b ]喹啉衍生物甲苯磺酸。对于内部炔烃，其α-亚氨基金卡宾通过乙烯基阳离子或烯基金卡宾与链状炔反应。两种途径最终都会导致生成4-酮-2-氨基吡咯衍生物。我们的机理分析表明，对于末端乙酰胺，水是比蒽乙更好的亲核试剂，而水和蒽甲对内部乙酰胺具有同等的反应性。

  DOI：

  10.1002/chem.201806083

文献信息

• Preparation of 3-Iodoquinolines from <i>N</i>-Tosyl-2-propynylamines with Diaryliodonium Triflate and <i>N</i>-Iodosuccinimide
  作者：Teppei Sasaki、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1021/acs.joc.7b01433

  日期：2017.11.17

  smoothly obtained in one pot by treating N-tosyl-2-propynylamines with diaryliodonium triflate in the presence of K3PO4 and a catalytic amount of CuCl at room temperature, followed by treatment with N-iodosuccinimide and BF3·OEt2 at 0 °C, and then NaOH in methanol solution. The product, 3-iodo-4-phenylquinoline was smoothly transformed into 4-phenylquinoline with zinc; 4-phenyl-3-toluenesulfenylquinoline with

  在室温下，在K 3 PO 4和催化量的CuCl存在下，用三氟甲磺酸二芳基di酯处理N-甲苯磺酰基-2-丙炔胺，可以在一锅中顺利获得4-芳基和4-烷基取代的3-碘喹啉。在0°C下用N-碘琥珀酰亚胺和BF 3 ·OEt 2处理，然后在甲醇溶液中用NaOH处理。将产物3-碘-4-苯基喹啉用锌平稳地转化为4-苯基喹啉；4-苯基-3-甲苯磺酰基喹啉与甲苯硫醇，K 2 CO 3和CuI; 4-苯基-3-苯基乙炔基喹啉与Sonogashira偶联反应；与4-苯基-3-苯乙烯基喹啉发生Heck偶联反应；3,4-二苯基喹啉与铃木-宫浦偶联反应；2-环己基-3-碘-4-苯基喹啉与环己烷羧酸，Ag 2 CO 3和K 2 S 2 O 8；和3-碘-2-（2'，5'-二恶烷-1'-基）-4-苯基喹啉与过氧化苯甲酰在二恶烷中。
• 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。
• Gold(I)‐Catalyzed and PTSA‐Promoted Cycloisomerization of Ynamides to Access Pyrrole Substituted α,β‐Unsaturated Ketones**
  作者：Shivani Choudhary、Gayyur、Nayan Ghosh

  DOI：10.1002/ejoc.202201223

  日期：2023.1.24

  In this work, a new ynamide scaffold has been designed, synthesized and later applied in a gold-catalyzed cycloisomerization reaction to access pyrrole containing α,β-unsaturated ketones in low-to-moderate yields. Interestingly, the trans product has been obtained as a major isomer.

  在这项工作中，设计、合成了一种新的 ynamide 支架，随后将其应用于金催化的环化异构化反应，以低至中等收率获得含有 α,β-不饱和酮的吡咯。有趣的是，反式产物已作为主要异构体获得。
• Gold‐Catalyzed Annulations of <i>N</i> ‐Propargyl Ynamides with Anthranils with Two Distinct Chemoselectivities
  作者：Yu‐Chen Hsu、Shu‐An Hsieh、Rai‐Shung Liu

  DOI：10.1002/chem.201806083

  日期：2019.4.5

  Gold‐catalyzed annulation of N‐propargyl ynamides with anthranils can proceed by two distinct mechanisms. In the case of a terminal N‐propargyl ynamide, its resulting α‐imino gold carbene reacts with a tethered alkyne to generate a vinyl cation to enable hydrolysis, which ultimately yields a pyrrolo[2,3‐b]quinoline derivative after treatment with p‐toluenesulfonic acid. For an internal alkyne, its

  金催化的N-炔丙基乙酰胺与蒽的环化反应可以通过两种不同的机理进行。在末端N-炔丙基炔基酰胺的情况下，其生成的α-亚氨基金卡宾与链状炔反应生成乙烯基阳离子以实现水解，经p处理后最终生成吡咯并[2,3- b ]喹啉衍生物甲苯磺酸。对于内部炔烃，其α-亚氨基金卡宾通过乙烯基阳离子或烯基金卡宾与链状炔反应。两种途径最终都会导致生成4-酮-2-氨基吡咯衍生物。我们的机理分析表明，对于末端乙酰胺，水是比蒽乙更好的亲核试剂，而水和蒽甲对内部乙酰胺具有同等的反应性。
• 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.