2-methoxy-N-tosylbenzamide | 81589-32-4

• 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: 2-methoxy-N-tosylbenzamide
• 英文别名: 2-methoxy-N-(4-methylbenzenesulfonyl)benzenecarboxamide；2-methoxy-N-(4-methylphenyl)sulfonylbenzamide
• CAS: 81589-32-4
• 化学式: C₁₅H₁₅NO₄S
• 分子量: 305.354
• InChiKey: BCWLMIVSEHEFHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  99-101 °C
• 密度：
  1.273±0.06 g/cm3(Predicted)
• 溶解度：
  >45.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-N-tosylbenzamide 在 potassium permanganate 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Design of novel CSA analogues as potential safeners and fungicides

  摘要：

  Study of safeners has been seldom reported in literature. In this work, a series of novel acylsulfamoylbenzamide analogues was designed and synthesized with newly developed safener cyprosulfamide (CSA) as the leading compound. The activity assay against the herbicide thiencarbazone-methyl (TCM) on maize revealed that fifteen compounds showed better protective effect than CSA on the fresh weight of aerial parts, twelve compounds exhibited better activity on the dry weight of aerial parts. Remarkably, two compounds (6Ih, 7II) had protective effect on the four aspects of TCM treated maize. Further antifungal assay showed their excellent activity against Physollospora piricola. The structure-activity relationships of CSA analogues as safeners and fungicides were discussed and it might be valuable for further molecular modification of new CSA analogues. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.085
• 作为产物：
  描述：

  三甲基-(4-甲基苯基)锡烷 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 2-methoxy-N-tosylbenzamide
  参考文献：
  名称：

  Tin for organic synthesis. 10. Unconventional regiospecific syntheses of aromatic carbonamides and thiocarbonamides by means of tin-mediated Friedel-Crafts reactions

  摘要：

  Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group. Thus, unconventionally substituted aromatic carbonamides can be obtained. The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings. The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22. One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29. Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28. From the reactions of 1 with ethoxycarbonyl isothiocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible. The scope, limitations, and mechanism of these electrophilic substitutions are outlined.

  DOI：

  10.1021/jo00077a020

文献信息

• Controllable construction of isoquinolinedione and isocoumarin scaffolds <i>via</i> Rh^III-catalyzed C–H annulation of <i>N</i>-tosylbenzamides with diazo compounds
  作者：Yanfei Liu、Jiaping Wu、Baiyang Qian、Yongjia Shang

  DOI：10.1039/c9ob01789e

  日期：——

  An efficient protocol for the synthesis of isoquinolinediones by Rh^III-catalyzed C–H activation/annulation/decarboxylation of N-tosylbenzamides with diazo compounds is reported.

  一种高效的协议报告了通过Rh^III催化的C-H活化/环化/脱羧反应，用双氮化合物与对甲苯磺酰苯甲酰胺合成异喹啉二酮。
• Heteroannulation enabled by a bimetallic Rh(<scp>iii</scp>)/Ag(<scp>i</scp>) relay catalysis: application in the total synthesis of aristolactam BII
  作者：Wei-Wei Ji、E. Lin、Qingjiang Li、Honggen Wang

  DOI：10.1039/c7cc02105d

  日期：——

  redox-neutral bimetallic Rh(III)/Ag(I) relay catalysis allowed the efficient construction of 3-alkylidene isoindolinones and 3-alkylidene isobenzofuranones. The Rh(III) catalyst was responsible for the C–H monofluoroalkenylation reaction, whereas the Ag(I) salt was an activator for the follow-up cyclization. The methodology developed was applied as a key step in the rapid total synthesis of the natural product

  氧化还原中性的双金属Rh（III）/ Ag（I）中继催化可以有效地构建3-亚烷基异吲哚满酮和3-亚烷基异苯并呋喃酮。Rh（III）催化剂负责C–H单氟烯基化反应，而Ag（I）盐则是后续环化反应的活化剂。所开发的方法学被用作快速合成天然产物马兜铃内酰胺BII的关键步骤。
• Ru(<scp>ii</scp>)-catalyzed allenylation and sequential annulation of <i>N</i>-tosylbenzamides with propargyl alcohols
  作者：Shreemoyee Kumar、Akshay M. Nair、Chandra M. R. Volla

  DOI：10.1039/d1cc01768c

  日期：——

  We hereby report Ru(II)-catalyzed C(sp2)–H allenylation of N-tosylbenzamides to access multi-substituted allenylamides. Furthermore, the allenylamides were converted to the corresponding isoquinolone derivatives via base mediated annulation. The current protocol features low catalyst loading, mild reaction conditions, high functional group compatibility and desired scalability. The unique functionality

  我们在此报告了 Ru( II ) 催化的N-甲苯磺酰苯甲酰胺的C(sp 2 )–H 烯丙基化以获得多取代的烯丙基酰胺。此外，通过碱介导的环化将丙二烯基酰胺转化为相应的异喹诺酮衍生物。目前的协议具有催化剂负载低、反应条件温和、官能团兼容性高和所需的可扩展性等特点。所提供的丙二烯的独特功能允许进一步转换以扩展协议的实用性。
• A simple, efficient Pd-catalyzed synthesis of N-sulfonylimines from organoboronic acids and tosylbenzimidoyl chlorides
  作者：Li-Yan Fan、Fei-Feng Gao、Wei-Hua Jiang、Min-Zhi Deng、Chang-Tao Qian

  DOI：10.1039/b802867b

  日期：——

  A simple and efficient synthesis of N-sulfonyl ketimines through a Pd-catalyzed cross-coupling reaction between organoboronic acids and tosylbenzimidoyl chlorides under mild conditions has been developed.

  通过温和的条件下有机硼酸和甲苯磺酰苯甲酰氯之间的钯催化交叉偶联反应，可以简单有效地合成N-磺酰基酮亚胺。
• Ruthenium Oxidase Catalysis for Site-Selective C-H Alkenylations with Ambient O₂ as the Sole Oxidant
  作者：Alexander Bechtoldt、Carina Tirler、Keshav Raghuvanshi、Svenja Warratz、Christoph Kornhaaß、Lutz Ackermann

  DOI：10.1002/anie.201507801

  日期：2016.1.4

  Ruthenium(II) oxidase catalysis by direct dioxygen‐coupled turnover enabled step‐economical oxidative CH alkenylation reactions at ambient pressure. Versatile ruthenium(II) biscarboxylate catalysts displayed ample substrate scope and proved applicable to weakly coordinating and removable directing groups. The twofold CH functionalization strategy was characterized by exceedingly mild reaction conditions

  直接双氧偶联的周转率催化钌（II）氧化酶在环境压力下实现了分步经济的氧化CH烯基化反应。多功能的双羧酸钌（II）催化剂显示出足够的底物范围，并证明适用于弱配位和可除去的导向基团。双重CH官能化策略的特点是反应条件极其温和，并且具有出色的位置选择性。