N-(4-甲氧基苯甲酰基)-4-甲基苯磺酰胺 | 58734-14-8

• 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: N-(4-甲氧基苯甲酰基)-4-甲基苯磺酰胺
• 英文名称: 4-methoxy-N-tosylbenzamide
• 英文别名: 4-methoxy-N-(4-methylphenyl)sulfonylbenzamide
• CAS: 58734-14-8
• 化学式: C₁₅H₁₅NO₄S
• 分子量: 305.354
• InChiKey: UIVBALBJIQFSFO-UHFFFAOYSA-N

物化性质

• 熔点：
  176 °C(Solv: ethanol (64-17-5))
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  N-(4-甲氧基苯甲酰基)-4-甲基苯磺酰胺 在 五氯化磷 、 三氯氧磷 作用下， 以 苯 为溶剂， 生成 Anis-N-tosyl-imidchlorid
  参考文献：
  名称：

  钯催化的2,3-烯丙基胺和芳基碘化物的环化反应合成2-咪唑啉

  摘要：

  描述了通过钯催化的2，3-烯丙基胺与芳基碘化物合成多取代的2-咪唑啉衍生物的有效方法。这种简单的多米诺骨牌工艺可以在一个合成操作中形成新的碳-碳和碳-氮键。

  DOI：

  10.1055/s-0037-1610742
• 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 N-(4-甲氧基苯甲酰基)-4-甲基苯磺酰胺
  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。
• Iodide as an Activating Agent for Acid Chlorides in Acylation Reactions
  作者：Russell J. Wakeham、James E. Taylor、Steven D. Bull、James A. Morris、Jonathan M. J. Williams

  DOI：10.1021/ol400035f

  日期：2013.2.1

  Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel–Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.

  可以使用简单的碘源活化酰氯，使其受到各种相对较弱的亲核试剂的亲核攻击。其中包括N-甲基吡咯的Friedel-Crafts酰化，磺酰胺的N-酰化以及受阻酚衍生物的酰化反应。据信该反应通过过渡性碘酸中间体进行。
• <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。
• Direct Acyl Substitution of Carboxylic Acids: A Chemoselective O- to N-Acyl Migration in the Traceless Staudinger Ligation
  作者：Andrew D. Kosal、Erin E. Wilson、Brandon L. Ashfeld

  DOI：10.1002/chem.201201773

  日期：2012.11.5

  chlorophosphite‐modified, Staudinger‐like acylation of azides involving a highly chemoselective, direct nucleophilic acyl substitution of carboxylic acids is described. The reaction provides the corresponding amides with analytical purity in 32–97 % yield after a simple aqueous workup without the need for a pre‐activation step. The use of chlorophosphites as dual carboxylic acid–azide activating agents

  描述了叠氮化物的氯亚磷酸酯修饰的，类似于Staudinger的酰化反应，涉及羧酸的高度化学选择性，直接亲核酰基取代。在简单的水溶液处理后，该反应可提供相应的分析纯度的酰胺，产率为32–97％，而无需预活化步骤。在多种亲核和亲电官能团（包括胺，醇，酰胺，醛和酮）的存在下，使用氯代亚磷酸酯作为双羧酸-叠氮化物活化剂可以形成酰基CN键。描述了用于形成烷基酰胺，磺酰基酰胺，内酰胺和二肽的羧酸和叠氮化物的偶联。