N-(2-(p-tolylethynyl)phenyl)methanesulfonamide | 1351667-31-6

• 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-(2-(p-tolylethynyl)phenyl)methanesulfonamide
• 英文别名: N-[2-[2-(4-methylphenyl)ethynyl]phenyl]methanesulfonamide
• CAS: 1351667-31-6
• 化学式: C₁₆H₁₅NO₂S
• 分子量: 285.367
• InChiKey: BKCVVJWPBINUDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 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-allyl-O-benzoyl-N-methylhydroxylamine 、 N-(2-(p-tolylethynyl)phenyl)methanesulfonamide 在 copper(II) bis(trifluoromethanesulfonate) 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以30%的产率得到N-allyl-N-methyl-1-methanesulfonyl-2-(4-methylphenyl)-indol-3-amine
  参考文献：
  名称：

  An Annulative Electrophilic Amination Approach to 3-Aminobenzoheteroles

  摘要：

  A copper-catalyzed annulative amination approach to 3-aminobenzofurans and -indoles from o-alkynylphenols and -anilines has been developed. The Cu-based catalysis is based on an umpolung, electrophilic amination with O-benzoyl hydroxylamines and enables the mild and convergent synthesis of various 3-aminobenzoheteroles of biological and pharmaceutical interest. Some mechanistic investigations and an application of this protocol to construction of more complex tricyclic framework are also described.

  DOI：

  10.1021/jo202207s
• 作为产物：
  描述：

  2-碘苯胺 生成 N-(2-(p-tolylethynyl)phenyl)methanesulfonamide
  参考文献：
  名称：

  An Annulative Electrophilic Amination Approach to 3-Aminobenzoheteroles

  摘要：

  A copper-catalyzed annulative amination approach to 3-aminobenzofurans and -indoles from o-alkynylphenols and -anilines has been developed. The Cu-based catalysis is based on an umpolung, electrophilic amination with O-benzoyl hydroxylamines and enables the mild and convergent synthesis of various 3-aminobenzoheteroles of biological and pharmaceutical interest. Some mechanistic investigations and an application of this protocol to construction of more complex tricyclic framework are also described.

  DOI：

  10.1021/jo202207s

文献信息

• Pd-Catalyzed Enantioselective Tandem C–C Bond Activation/Cacchi Reaction between Cyclobutanones and <i>o</i>-Ethynylanilines
  作者：Wan-Chun Yang、Xiao-Bing Chen、Kun-Long Song、Bin Wu、Wan-Er Gan、Zhan-Jiang Zheng、Jian Cao、Li-Wen Xu

  DOI：10.1021/acs.orglett.0c04297

  日期：2021.2.19

  A palladium-catalyzed asymmetric tandem C–C bond activation/Cacchi reaction between cyclobutanones and o-ethynylanilines was reported. The transient chiral σ-alkylpalladium species generated via enantioselective C(sp3)–C(sp2) bond activation of cyclobutanones promotes cyclization of o-ethynylanilines, leading to one-carbon-tethered chiral indanone-substituted indoles. Two C–C bonds and one C–N bond

  据报道，环丁酮与邻乙炔基苯胺之间存在钯催化的不对称串联CC键活化/ Cacchi反应。通过环丁酮的对映选择性C（sp 3）–C（sp 2）键活化而产生的瞬时手性σ-烷基钯物质，促进了邻乙炔基苯胺的环化反应，从而导致一碳束缚的手性茚满酮取代的吲哚。伴随着全碳四元立体中心的形成，产生了两个C–C键和一个C–N键。此外，可以在2，3-二取代的吲哚部分中形成手性C 2-芳基轴，从而导致具有中心和轴向立体生成元素的茚满酮取代的吲哚。
• 一种手性吲哚类化合物及其制备方法
  申请人：杭州师范大学

  公开号：CN112321481B

  公开（公告）日：2022-06-10

  本发明公开了一种手性吲哚类化合物及其制备方法。以苯环邻位具有碘取代的环丁酮类化合物和邻位具有乙炔基取代的芳基磺酰胺类化合物为反应物，在钯盐的催化下，以TADDOL衍生的亚磷酰胺类化合物为手性配体，在碱性条件下进行不对称开环环化‑串联反应合成式(I)所示的手性吲哚类化合物。该方法对有不同取代的环丁酮和磺酰胺都具有比较好的适应性，可以得到良好的产率和优异的对映选择性。
• PIFA/Ar₂Te₂‐Mediated Synthesis of 3‐Aryltelluroindoles <i>via</i> Intramolecular Cyclization of 2‐Alkynylanilines
  作者：Jianing Zhang、Zhenyang Yu、Haofeng Shi、Lingzhi Xu、Yixuan Song、Yunfei Du

  DOI：10.1002/ejoc.202301059

  日期：2024.2.5

  The reaction of 2-alkynylanilines with phenyliodonium bis(trifluoroacetate) (PIFA) and diaryl ditellurides was found to conveniently afford the corresponding 3-aryltelluroindoles via oxidative cyclization/tellurolation. A plausible mechanism involving the in situ formation of the reactive ArTeOCOCF3 from the reaction of PIFA and diaryl ditellurides, and the subsequent oxidative C−N/C−Te bond formations

  发现2-炔基苯胺与双(三氟乙酸)苯基碘(PIFA)和二芳基二碲化物的反应可以通过氧化环化/碲化方便地得到相应的3-芳基碲吲哚。假设了一种可能的机制，涉及通过 PIFA 和二芳基二碲化物的反应原位形成反应性 ArTeOCOCF 3，以及随后形成氧化性 CN/C-Te 键。
• An Annulative Electrophilic Amination Approach to 3-Aminobenzoheteroles
  作者：Naoki Matsuda、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo202207s

  日期：2012.1.6

  A copper-catalyzed annulative amination approach to 3-aminobenzofurans and -indoles from o-alkynylphenols and -anilines has been developed. The Cu-based catalysis is based on an umpolung, electrophilic amination with O-benzoyl hydroxylamines and enables the mild and convergent synthesis of various 3-aminobenzoheteroles of biological and pharmaceutical interest. Some mechanistic investigations and an application of this protocol to construction of more complex tricyclic framework are also described.