N-benzyl-propanesulfonamide | 207574-06-9

• 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-propanesulfonamide
• 英文别名: N-(benzyl)propylsulfonamide；N-benzylpropane-1-sulfonamide
• CAS: 207574-06-9
• 化学式: C₁₀H₁₅NO₂S
• mdl: MFCD16172038
• 分子量: 213.301
• InChiKey: IFJVPCQTFRRSQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-propanesulfonamide 在 4-二甲氨基吡啶 、 四乙基氯化铵 、 potassium carbonate 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Regioselective synthesis of N-substituted-4-substituted isothiazolidine-1,1-dioxides

  摘要：

  A novel and efficient synthesis of a range of racemic and enantioenriched N-substituted-4-substituted isothiazolidine-1, 1-dioxides from epoxides and sulfonamides is described. The critical choice of the activating group for the cyclization event is discussed. The application of this methodology to the synthesis of N-substituted-4,5-disubstituted derivatives is also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.038
• 作为产物：
  描述：

  丙基磺酰氯 、 苄胺 以 乙酸乙酯 为溶剂， 反应 1.0h， 以96%的产率得到N-benzyl-propanesulfonamide
  参考文献：
  名称：

  可见光光氧化还原催化吡咯的无金属CH磺酰胺化

  摘要：

  我们报告了一步法从磺酰胺和吡咯制备N-（2-吡咯）-磺酰胺的过程。反应使用可见光，,啶染料作为光催化剂，氧气作为末端氧化剂。

  DOI：

  10.1039/c6cc06111g

文献信息

• Preparation of Sulfonamides from Sodium Sulfonates: Ph3P ⋅ Br2 and Ph3P ⋅ Cl2 as a Mild Halogenating Reagent for Sulfonyl Bromides and Sulfonyl Chlorides
  作者：Tadashi Kataoka、Tetsuo Iwama、Tomofumi Setta、Atsuko Takagi

  DOI：10.1055/s-1998-4488

  日期：1998.4

  Arene- and alkanesulfonamides were prepared by treatment of the corresponding sodium sulfonates with triphenylphosphine dibromide or dichloride followed by amines in the presence of triethylamine via sulfonyl halides. Reactions of sodium aminosulfonates gave cyclized products. Amidation of p-toluenesulfonic acid with triphenylphosphine dichloride was also examined to give N-benzyl-p-toluenesulfonamide. Methyl p-toluenesulfonate was obtained by esterification of sodium p-toluenesulfonate via p-toluenesulfonyl chloride.

  通过在三乙胺存在下，将相应的磺酸钠与三苯基膦二溴化物或二氯化物反应生成磺酰卤，随后与胺反应，制备了芳基磺酰胺和烷基磺酰胺。氨基磺酸钠的反应得到了环化产物。还研究了使用三苯基膦二氯化物与对甲苯磺酸的胺化反应，生成了N-苄基对甲苯磺酰胺。通过将对甲苯磺酰氯与对甲苯磺酸钠酯化，得到了甲基对甲苯磺酸酯。
• Synthesis and Reactivity of Polydisulfonimides
  作者：Benjamin T. Burlingham、Theodore S. Widlanski

  DOI：10.1021/ja002465v

  日期：2001.4.1

  oligomers, previously unreported reactivity of the N-substituted disulfonimide functional group was discovered. Under basic conditions, unexpected lengthening of the oligomers occurs through a "transdisulfonimidation" reaction, whereby new disulfonimides are synthesized from existing ones by reaction with sulfonamide anion. This process appears to proceed via formation of a sulfene intermediate. Support for

  首次合成烷基二磺酰亚胺低聚物。在合成这些低聚物的过程中，发现了以前未报道的 N-取代二磺酰亚胺官能团的反应性。在碱性条件下，低聚物通过“转二磺酰亚胺化”反应发生意外延长，由此通过与磺酰胺阴离子反应从现有二磺酰亚胺合成新的二磺酰亚胺。该过程似乎是通过形成亚砜中间体来进行的。对 E1cB(Rev) 机制的支持包括同位素加扰、取代基效应和亚砜捕获。
• Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines
  作者：Jian Wang、Wen-Jing Yi

  DOI：10.3390/molecules24203771

  日期：——

  through the oxidation of sulfonamides mediated by N-hydroxyphthalimide under mild conditions has been developed. Compared to reported oxidation methods, broader substrates scope and milder conditions were achieved in our method. Importantly, this oxidation method can afford N-sulfonyl enaminones using Mannich products as starting materials. Additionally, the one-pot Friedel–Crafts arylation reaction of unseparated

  开发了一种在温和条件下通过 N-羟基邻苯二甲酰亚胺介导的磺酰胺氧化制备磺酰亚胺的新方法。与报道的氧化方法相比，我们的方法实现了更广泛的底物范围和更温和的条件。重要的是，这种氧化方法可以使用曼尼希产物作为起始原料提供 N-磺酰基烯胺酮。此外，在我们的系统中形成的未分离的 N-磺酰亚胺与 1,3,5-三甲氧基苯的一锅 Friedel-Crafts 芳基化反应在没有任何额外催化剂的情况下是成功的。
• Metal-free C–H sulfonamidation of pyrroles by visible light photoredox catalysis
  作者：Andreas Uwe Meyer、Anna Lucia Berger、Burkhard König

  DOI：10.1039/c6cc06111g

  日期：——

  We report a one-step procedure for the preparation of N-(2-pyrrole)-sulfonamides from sulfonamides and pyrroles. The reaction uses visible light, an acridinium dye as photocatalyst and oxygen as the terminal oxidant...

  我们报告了一步法从磺酰胺和吡咯制备N-（2-吡咯）-磺酰胺的过程。反应使用可见光，,啶染料作为光催化剂，氧气作为末端氧化剂。
• Regioselective synthesis of N-substituted-4-substituted isothiazolidine-1,1-dioxides
  作者：Ed Cleator、Faye J. Sheen、Matthew M. Bio、K.M. Jos Brands、Antony J. Davies、Ulf-H. Dolling

  DOI：10.1016/j.tetlet.2006.04.038

  日期：2006.6

  A novel and efficient synthesis of a range of racemic and enantioenriched N-substituted-4-substituted isothiazolidine-1, 1-dioxides from epoxides and sulfonamides is described. The critical choice of the activating group for the cyclization event is discussed. The application of this methodology to the synthesis of N-substituted-4,5-disubstituted derivatives is also described. (c) 2006 Elsevier Ltd. All rights reserved.