4-甲基-N-[(4-甲基苯基)磺酰基]苯甲酰胺 | 120336-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲基-N-[(4-甲基苯基)磺酰基]苯甲酰胺
• 英文名称: 4-methyl-N-tosylbenzamide
• 英文别名: 4-methyl-N-(4-methylphenyl)sulfonylbenzamide
• CAS: 120336-96-1
• 化学式: C₁₅H₁₅NO₃S
• 分子量: 289.355
• InChiKey: PKNBPSWKOWSXJH-UHFFFAOYSA-N

物化性质

• 溶解度：
  >43.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  4-甲基-N-[(4-甲基苯基)磺酰基]苯甲酰胺 在 四乙基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到对甲苯酰胺
  参考文献：
  名称：

  Superoxide‐Mediated Regioselective Deblocking of the Tosyl Group from N‐Tosylcarboxamides

  摘要：

  DOI：

  10.1080/00397910600775416
• 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 4-甲基-N-[(4-甲基苯基)磺酰基]苯甲酰胺
  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。
• Pd(II)/Cu(II)-Catalyzed Regio- and Stereoselective Synthesis of (<i>E</i>)-3-Arylmethyleneisoindolin-1-ones Using Air as the Terminal Oxidant
  作者：So Won Youn、Tae Yun Ko、Young Ho Kim、Yun Ah Kim

  DOI：10.1021/acs.orglett.8b03409

  日期：2018.12.21

  Regio- and stereoselective synthesis of (E)-3-arylmethyleneisoindolin-1-ones via Pd(II)/Cu(II)-catalyzed one-pot C–C/C–N bond forming sequence between amides and styrenes is reported. This method provides facile and rapid access to a diverse range of such compounds using readily available starting materials under mild aerobic conditions with good functional group tolerance and high selectivity and efficiency

  据报道，通过Pd（II）/ Cu（II）催化的酰胺与苯乙烯之间的一锅CC-C / C-N键形成序列的区域和立体选择性合成（E）-3-芳基亚甲基异吲哚啉-1-酮。在温和的好氧条件下，使用易得的起始原料，该方法可以轻松，快速地获得各种化合物，并具有良好的官能团耐受性，高选择性和高效率。从该方法获得的产物的进一步精制使得马兜铃内酰胺和吲哚异喹啉酮生物碱的合成非常短而有效。
• <scp>Pd‐Catalyzed</scp> Asymmetric Synthesis of 3, <scp>4‐Dihydroisoquinolinones</scp> From <scp> <i>N</i> ‐Ts‐Benzamides </scp> and 1, <scp>3‐Dienes</scp>
  作者：Tae Kyun Kim、So Won Youn

  DOI：10.1002/bkcs.12227

  日期：2021.3

  A Pd(II)‐catalyzed asymmetric oxidative annulation of N‐Ts‐benzamides with 1,3‐dienes using a chiral pyridine‐oxazoline‐type ligand for the regio‐ and stereoselective synthesis of chiral 3,4‐dihydroisoquinolinones has been developed.

  已经开发了一种Pd（II）催化的N -Ts-苯甲酰胺与1,3-二烯的不对称氧化环合反应，使用手性吡啶-恶唑啉型配体进行手性3,4-二氢异喹啉酮的区域和立体选择性合成。
• N-Sulfonyl acetylketenimine as a highly reactive intermediate for synthesis of N-Aroylsulfonamides
  作者：Weiguang Yang、Dayun Huang、Xiaobao Zeng、Jianlan Zhang、Xinyan Wang、Yuefei Hu

  DOI：10.1016/j.tet.2018.12.005

  日期：2019.1

  A highly reactive intermediate N-sulfonyl acetylketenimine was generated from an ynone-participated CuAAC/ring-opening method. Its unique structure allowed it to react with aryl carboxylic acids to give N-aroylsulfonamides via a novel Mumm-type rearrangement.

  高反应活性的中间体N-磺酰基乙酰酮亚胺是通过参与炔酮的CuAAC /开环方法生成的。它独特的结构使其能够与芳基羧酸反应，通过新颖的Mumm型重排反应生成N-芳酰基磺酰胺。
• 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。