N-(4-((2-tosylhydrazono)methyl)phenyl)acetamide | 18708-53-7

• 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-(4-((2-tosylhydrazono)methyl)phenyl)acetamide
• 英文别名: N-[4-[[(4-methylphenyl)sulfonylhydrazinylidene]methyl]phenyl]acetamide
• CAS: 18708-53-7
• 化学式: C₁₆H₁₇N₃O₃S
• 分子量: 331.395
• InChiKey: NGMKRGVLFSGKIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  96
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-((2-tosylhydrazono)methyl)phenyl)acetamide 、 N-(4-氰基-3-三氟甲基苯基)甲基丙烯酰胺 在 sodium hydride 作用下， 生成 5-(4-acetylamino-phenyl)-3-methyl-3,4-dihydro-2H-pyrazole-3-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide
  参考文献：
  名称：

  Synthesis and SAR of novel hydantoin derivatives as selective androgen receptor modulators

  摘要：

  A novel series of hydantoin derivatives were identified by in vivo studies as tissue selective androgen receptor modulators. SAR around this series revealed that the function of the ligand could be altered by minor structural modification. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.084
• 作为产物：
  描述：

  对乙酰氨基苯甲醛 、 对甲苯磺酰肼 以 甲醇 为溶剂， 生成 N-(4-((2-tosylhydrazono)methyl)phenyl)acetamide
  参考文献：
  名称：

  可回收铜 (I) 催化的三烷基甲硅烷基乙炔和 N-甲苯磺酰腙的交叉偶联导致 C(sp)–C(sp3) 键的形成

  摘要：

  通过 Cu 卡宾迁移插入和 SBA-15-固定的l-脯氨酸-Cu (I ) 络合物 [SBA-15- l -Proline-CuI] 作为催化剂和 LiO t Bu 作为碱，导致 C(sp)–C(sp 3 ) 键的形成。该反应以中高产率生成多种烷基三烷基甲硅烷基炔烃。这种新型多相铜 (I) 配合物具有与均相 CuI 相当的催化效率，并且可以通过简单的离心过程轻松回收，并且可回收多达 12 次而不会显着损失活性。

  DOI：

  10.1021/acs.joc.2c02691

文献信息

• Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
  作者：Shun Wang、Bei-Yi Cheng、Matea Sršen、Burkhard König

  DOI：10.1021/jacs.0c00629

  日期：2020.4.22

  catalysis with the Wolff–Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff–Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles

  光氧化还原催化与沃尔夫-基什纳 (WK) 反应相结合，可以通过自由基-碳负离子中继序列（光沃尔夫-基什纳反应）对羰基进行双官能化。光氧化还原引发自由基加成至 N-磺酰腙，按照 WK 型机制产生 α-功能化碳负离子。对于以硫为中心的自由基，碳负离子通过与包括 CO2 和醛在内的亲电子试剂反应而进一步官能化，而 CF3 自由基加成则通过生成的 α-CF3 碳负离子的 β-氟化物消除提供了多种偕二氟烯烃。 80 多个底物示例证明了该反应序列的广泛适用性。包括自由基抑制、氘标记、荧光猝灭、循环伏安法和控制实验在内的一系列研究支持了所提出的自由基-碳负离子中继机制。
• One-Step Synthesis of Sulfonamides from <i>N</i>-Tosylhydrazones
  作者：Andy S. Tsai、John M. Curto、Benjamin N. Rocke、Anne-Marie R. Dechert-Schmitt、Gajendrasingh K. Ingle、Vincent Mascitti

  DOI：10.1021/acs.orglett.5b03545

  日期：2016.2.5

  The first described reaction between N-tosylhydrazone and SO2 is reported to provide alkyl sulfonamides in the presence of various amines. In this procedurally simple method, hydrazones of both unsaturated aldehydes and ketones proceed in moderate to excellent yields. Primary and secondary aliphatic amines are accommodated in this reaction, which provides a novel route to sulfonamides.

  据报道，首先描述的N-甲苯磺酰and和SO 2之间的反应在各种胺的存在下提供了烷基磺酰胺。在此过程上简单的方法中，不饱和醛和酮的均以中等至极好的收率进行。伯和仲脂族胺被容纳在该反应中，这提供了磺酰胺的新途径。
• Synthesis of Terminal Allenes through Copper-Mediated Cross-Coupling of Ethyne with<i>N</i>-Tosylhydrazones or α-Diazoesters
  作者：Fei Ye、Chengpeng Wang、Xiaoshen Ma、Mohammad Lokman Hossain、Ying Xia、Yan Zhang、Jianbo Wang

  DOI：10.1021/jo502316q

  日期：2015.1.2

  Ethyne is employed as coupling partner in copper-mediated cross-coupling reactions with N-tosylhydrazones and alpha-diazoacetate, leading to the development of a new synthetic method for terminal allenes. With this novel coupling method, the terminal allenes were obtained in good yields and with excellent functional group tolerance. Copper carbene migratory insertion is proposed as the key step in these transformations.
• Synthesis and SAR of novel hydantoin derivatives as selective androgen receptor modulators
  作者：Xuqing Zhang、George F. Allan、Tifanie Sbriscia、Olivia Linton、Scott G. Lundeen、Zhihua Sui

  DOI：10.1016/j.bmcl.2006.08.084

  日期：2006.11

  A novel series of hydantoin derivatives were identified by in vivo studies as tissue selective androgen receptor modulators. SAR around this series revealed that the function of the ligand could be altered by minor structural modification. (c) 2006 Elsevier Ltd. All rights reserved.
• Recyclable Copper(I)-Catalyzed Cross-Coupling of Trialkylsilylethynes and <i>N</i>-Tosylhydrazones Leading to the Formation of C(sp)–C(sp³) Bonds
  作者：Qian Ye、Wencheng Huang、Li Wei、Mingzhong Cai

  DOI：10.1021/acs.joc.2c02691

  日期：2023.3.3

  A highly efficient heterogeneous copper(I)-catalyzed cross-coupling of trialkylsilylethynes with N-tosylhydrazones has been achieved in dioxane at 90–110 °C via the Cu carbene migratory insertion with an SBA-15-immobilized l-proline-Cu(I) complex [SBA-15-l-Proline-CuI] as the catalyst and LiOtBu as the base, leading to the formation of C(sp)–C(sp3) bonds. The reaction generates a wide variety of a

  通过 Cu 卡宾迁移插入和 SBA-15-固定的l-脯氨酸-Cu (I ) 络合物 [SBA-15- l -Proline-CuI] 作为催化剂和 LiO t Bu 作为碱，导致 C(sp)–C(sp 3 ) 键的形成。该反应以中高产率生成多种烷基三烷基甲硅烷基炔烃。这种新型多相铜 (I) 配合物具有与均相 CuI 相当的催化效率，并且可以通过简单的离心过程轻松回收，并且可回收多达 12 次而不会显着损失活性。