N-benzyl N-(tert-butoxycarbonyl) toluenesulfonamide | 170948-10-4

• 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: N-benzyl N-(tert-butoxycarbonyl) toluenesulfonamide
• 英文别名: tert-butyl N-benzyl-N-tosylcarbamate；tert-butyl N-benzyl-N-(4-methylphenyl)sulfonylcarbamate
• CAS: 170948-10-4
• 化学式: C₁₉H₂₃NO₄S
• 分子量: 361.462
• InChiKey: RISPBRSSYPTKTF-UHFFFAOYSA-N

物化性质

• 沸点：
  481.3±48.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl N-(tert-butoxycarbonyl) toluenesulfonamide 在 palladium dihydroxide 氢气 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 对甲苯磺酰胺
  参考文献：
  名称：

  A reversible safety-catch method for the hydrogenolysis of N-benzyl moieties

  摘要：

  The benzyl groups of beta-hydroxy-N-benzyl sulfonamides are labile toward hydrogenolysis-unlike N-benzyl sulfonamides lacking the beta-hydroxy moiety. We find that N-acyl-N-benzyl sulfonamides undergo hydrogenolysis under very mild conditions. Based upon these observations, we developed a reversible safety-catch method using tert-butoxycarbonyl moieties to activate N-benzyl sulfonamides toward hydrogenolysis. We also explored the utility of the safety-catch activation method for other nitrogen-based functionality such as N-benzyl carboxamides, imides, and related functionality. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.118
• 作为产物：
  描述：

  N-benzyl-N-(benzyloxycarbonyl) toluenesulfonamide 在 palladium dihydroxide 4-二甲氨基吡啶 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 N-benzyl N-(tert-butoxycarbonyl) toluenesulfonamide
  参考文献：
  名称：

  A reversible safety-catch method for the hydrogenolysis of N-benzyl moieties

  摘要：

  The benzyl groups of beta-hydroxy-N-benzyl sulfonamides are labile toward hydrogenolysis-unlike N-benzyl sulfonamides lacking the beta-hydroxy moiety. We find that N-acyl-N-benzyl sulfonamides undergo hydrogenolysis under very mild conditions. Based upon these observations, we developed a reversible safety-catch method using tert-butoxycarbonyl moieties to activate N-benzyl sulfonamides toward hydrogenolysis. We also explored the utility of the safety-catch activation method for other nitrogen-based functionality such as N-benzyl carboxamides, imides, and related functionality. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.118

文献信息

• N-Alkylation of Phthalimide, Carboxamide, and Sulfonamides By Oxdation–Reduction Condensation Using Di-<i>tert</i>-butyl-1,4-benzoquinone and Alkyl Diphenylphosphinite
  作者：Teruaki Mukaiyama、Hidenori Aoki

  DOI：10.1246/cl.2005.142

  日期：2005.2

  Various N-alkylamides were obtained in high yields under mild conditions by treating alkyl diphenylphosphinite with phthalimide, carboxamide or sulfonamides in the presence of 2,6-di-tert-butyl-1,4-benzoquinone (DBBQ) by oxdation–reduction condensation.

  在温和条件下，通过在2,6-二叔丁基-1,4-苯醌（DBBQ）的存在下，使烷基二苯基膦酸酯与邻苯二甲酰亚胺、羧酰胺或磺酰胺反应，获得了多种N-烷基酰胺，且产率较高。
• Mild, efficient cleavage of arenesulfonamides by magnesium reduction
  作者：Barthélémy Nyasse、Leif Grehn、Ulf Ragnarsson

  DOI：10.1039/a701408b

  日期：——

  The cleavage of arenesulfonamides via N-arenesulfonylcarbamates is achieved within a few minutes under ultrasonic conditions by reaction with magnesium in anhydrous methanol.

  在无水甲醇中，使用镁与N-芳基磺酰氨基碳酸酯的反应，在超声波条件下实现了芳基磺酰胺的裂解，仅需几分钟。
• Light-Driven Reductive Cleavage of Sulfonamides Promoted by Thiourea Organophotosensitizers
  作者：Jules Brom、Antoine Maruani、Laurent Micouin、Erica Benedetti

  DOI：10.1021/acs.joc.3c00296

  日期：2023.5.5

  We have developed a practical method to perform the reductive photocleavage of sulfonamides using thioureas as organophotocatalysts. This transformation, which tolerates a variety of substrates, occurs under mild reaction conditions in the presence of tetrabutylammonium borohydride as a reducing agent. Experimental and theoretical mechanistic investigations complete the study, shedding light on the

  我们开发了一种使用硫脲作为有机光催化剂进行磺胺类药物还原光裂解的实用方法。这种可耐受多种底物的转化在四丁基硼氢化铵作为还原剂存在的温和反应条件下发生。实验和理论机理研究完成了这项研究，揭示了参与光催化过程的活性物质的性质。
• [2.2]Paracyclophane-based coumarins: effective organo-photocatalysts for light-induced desulfonylation processes
  作者：Jules Brom、Antoine Maruani、Serge Turcaud、Sonia Lajnef、Fabienne Peyrot、Laurent Micouin、Erica Benedetti

  DOI：10.1039/d3ob01711g

  日期：——

  Herein, we demonstrate for the first time that coumarins derived from [2.2]paracyclophane (pCp) can act as effective organo-photocatalysts and promote the reductive cleavage of sulfonamides under light-irradiation. In the presence of these original compounds, photodesulfonylation reactions occur under mild conditions at low catalyst loadings in the presence of Hantzsch ester. Theoretical and experimental

  在此，我们首次证明源自[2.2]对环芳烷（pCp）的香豆素可以作为有效的有机光催化剂并促进磺酰胺在光照射下的还原裂解。在这些原始化合物存在下，光脱磺酰化反应在 Hantzsch 酯存在下、在低催化剂负载量的温和条件下发生。描述了理论和实验研究，阐明了光催化过程中涉及的反应机理和活性物质的性质。这项概念验证研究为 pCps 在光催化领域的进一步应用铺平了道路。
• Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation
  作者：Emma Alonso、Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(97)00920-4

  日期：1997.10

  The reaction of different protected alcohols, amines and amides with lithium and a catalytic amount of naphthalene (4 mol %) in THF at low temperature leads to their deprotection under very mild reaction conditions, the process being in many cases chemoselective. (C) 1997 Elsevier Science Ltd.