2-chloro-N-tosylbenzamide | 92290-83-0

• 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-chloro-N-tosylbenzamide
• 英文别名: 2-chloro-N-(4-methylbenzenesulfonyl)benzenecarboxamide；N-(2-Chlorobenzoyl)-4-methylbenzenesulfonamide；2-chloro-N-(4-methylphenyl)sulfonylbenzamide
• CAS: 92290-83-0
• 化学式: C₁₄H₁₂ClNO₃S
• 分子量: 309.773
• InChiKey: WHLOAQCDUFDNIA-UHFFFAOYSA-N

物化性质

• 熔点：
  121.0-122.5 °C
• 密度：
  1.360±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-N-tosylbenzamide 在 palladium diacetate 、 1-(125I)iodanylpyrrolidine-2,5-dione 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以50%的产率得到[¹²⁵I]-2-chloro-6-iodo-N-(4-methylbenzenesulfonyl)benzenecarboxamide
  参考文献：
  名称：

  Improvements of C–H Radio-Iodination of N-Acylsulfonamides toward Implementation in Clinics

  摘要：

  描述了一种改进的C-H放射性碘化协议。这些新条件允许使用[125I]NIS和少量钯醋酸盐和对甲苯磺酸催化快速干净地形成放射性碘化N-酰基磺酰胺。不需要预功能化的前体，产物以27-84%的放射化学转化率（RCC）获得。

  DOI：

  10.1055/s-0037-1611884
• 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 58.0h， 生成 2-chloro-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

• Co-Catalyzed Synthesis of <i>N</i>-Sulfonylcarboxamides from Carboxylic Acids and Sulfonyl Azides
  作者：Yue Fang、Zheng-Yang Gu、Shun-Yi Wang、Jin-Ming Yang、Shun-Jun Ji

  DOI：10.1021/acs.joc.8b01300

  日期：2018.8.17

  A Co-catalyzed effective synthesis of N-sulfonylcarboxamides from the reaction of carboxylic acids and organic azides in the presence of isocyanide has been developed. The protocol has the advantages of short time, low temperature, and being oxidant-free, which provides a new and simple approach for the synthesis of N-sulfonylcarboxamides in good to excellent yields with a broad substrate scope.

  已经开发了在异氰酸酯存在下由羧酸和有机叠氮化物的反应共催化有效合成N-磺酰基羧酰胺的方法。该方案具有时间短，温度低，无氧化剂的优点，为合成N-磺酰基甲酰胺提供了一种新的简单方法，具有良好的产率和良好的底物范围。
• 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。
• Metal-free C–H Activation over Graphene Oxide toward Direct Syntheses of Structurally Different Amines and Amides in Water
  作者：Prashant Shukla、Ambika Asati、Smita R. Bhardiya、Manorama Singh、Vijai K. Rai、Ankita Rai

  DOI：10.1021/acs.joc.0c02219

  日期：2020.12.4

  Unprecedented metal-free synthesis of a variety of amines and amides is reported via amination of C(sp3)–H and C(sp2)–H bonds. The strategy involves graphene-oxide/I2-catalyzed nitrene insertion using PhINTs as a nitrene (NT) source in water at room temperature. A wide range of structurally different substrates, viz., cyclohexane, cyclic ethers, arenes, alkyl aromatic systems, and aldehydes/ketones

  据报道，通过胺化C（sp 3）–H和C（sp 2）–H键，空前合成了多种胺和酰胺。该策略涉及在室温下使用PhINTs作为水中的腈（NT）源使用氧化石墨烯/ I 2催化的腈插入。尽管具有较低的收率，但已成功地使用各种结构不同的底物，即环己烷，环醚，芳烃，烷基芳族体系和具有α-苯环的醛/酮，以高收率获得了相应的腈插入产物在少数情况下。所设想的方法在操作简便性，无金属催化，使用水作为溶剂，环境反应条件和催化剂的可重复使用性方面均优于其他方法。
• Ruthenium-Catalyzed Synthesis of Isoindolinones via Amide-Directed Addition of Aromatic C-H Bonds to Aldimines
  作者：Hiroki Miura、Yuriko Kimura、Sachie Terajima、Tetsuya Shishido

  DOI：10.1002/ejoc.201801755

  日期：2019.5.8

  Straightforward Route! [RuCl2(p‐cymene)]2 promoted amide‐directed hydroarylation of aldimines in the presence of a catalytic amount of base gives the corresponding isoindolinone derivatives. A variety of amides and saldimines participated in the present Ru‐catalyzed reaction to furnish the corresponding isoindolinones in moderate to high yield. A variety of amides and aldimines participated in the

  直截了当的路线！[RuCl 2（p- cymene）] 2在催化量的碱存在下促进了醛胺的酰胺基加氢芳基化反应，得到了相应的异吲哚啉酮衍生物。多种酰胺和沙丁胺类药物参与了Ru催化的当前反应，以中等至高收率提供了相应的异吲哚啉酮。多种酰胺和醛亚胺参与了目前的Ru催化反应，以高至高收率提供了相应的异吲哚啉酮。
• 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。