N-methyl-C,N-diphenyl-methanesulfonamide | 61738-44-1

• 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-methyl-C,N-diphenyl-methanesulfonamide
• 英文别名: Phenyl-methansulfonsaeure-(N-methyl-anilid)；Benzylsulfonsaeure-methylanilid；Toluol-(α)-sulfonsaeure-N-methylanilid；Benzylsulfonsaeure-N-methyl-anilid；N-methyl-N,1-diphenylmethanesulfonamide
• CAS: 61738-44-1
• 化学式: C₁₄H₁₅NO₂S
• mdl: MFCD00159372
• 分子量: 261.345
• InChiKey: UNYWKVSYMGNIOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘苯 、 N-methyl-C,N-diphenyl-methanesulfonamide 在 bis(η3-allyl-μ-chloropalladium(II)) 、 potassium tert-butylate 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以71%的产率得到N-methyl-N,1,1-triphenylmethanesulfonamide
  参考文献：
  名称：

  Palladium-catalyzed benzylic direct arylation of benzyl sulfones with aryl halides

  摘要：

  An effective palladium catalyst system for the direct arylation of benzyl sulfones with aryl halides has been developed. The catalytic reaction provides a facile route to diarylmethyl sulfones. The products can be transformed further via desulfonylative functionalization mediated by aluminum compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.030
• 作为产物：
  描述：

  N,1-diphenylmethanesulfonamide 以88%的产率得到
  参考文献：
  名称：

  STARODUBTSEVA M. P.; SKRYPNIK YU. G.; VIZGERT R. B, VOPR. XIMII I XIM. TEXNOL., 1977, HO 49, 3-8

  摘要：

  DOI：

文献信息

• A Useful Pd-Catalyzed Negishi Coupling Approach to Benzylic Sulfonamide Derivatives
  作者：Gang Zhou、Pauline Ting、Robert Aslanian、John J. Piwinski

  DOI：10.1021/ol800785g

  日期：2008.6.1

  mild catalytic system to access diversely functionalized benzylic sulfonamides has been developed. Palladium-catalyzed alpha-arylation by Negishi cross-coupling of sulfonamide-stabilized anions and a wide range of aryl iodides, bromides, and triflates constitutes a practical strategy for the synthesis of various benzylic sulfonamides.

  已经开发出一种温和的催化体系，可以接触到各种官能化的苄基磺酰胺。Negishi交叉偶联磺酰胺稳定的阴离子与各种芳基碘化物，溴化物和三氟甲磺酸酯进行钯催化的α-芳基化反应，是合成各种苄基磺酰胺的实用策略。
• METHOD FOR DEPROTECTING ARYL OR ALKYL SULFONAMIDES OF PRIMARY OR SECONDARY AMINES
  申请人：Lefenfeld Michael

  公开号：US20090306391A1

  公开（公告）日：2009-12-10

  The invention relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by contacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material in the presence of a solid proton source under conditions sufficient to form the corresponding amine. The invention also relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by a) reacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material, and b) subsequently reacting the reaction product from step a) with an electrophile or a proton source. Preferred Stage 0 or Stage I alkali metal-silica gel materials include Na, K 2 Na, and Na 2 K.

  该发明涉及一种从一级或二级胺中去除烷基磺酰基或芳基磺酰基保护基的方法，方法包括将烷基磺酰胺或芳基磺酰胺与一种固体质子源接触，在足以形成相应胺的条件下，与0级或I级碱金属-硅胶材料反应。该发明还涉及一种从一级或二级胺中去除烷基磺酰基或芳基磺酰基保护基的方法，包括a)将烷基磺酰胺或芳基磺酰胺与0级或I级碱金属-硅胶材料反应，b)随后将步骤a)中的反应产物与亲电试剂或质子源反应。首选的0级或I级碱金属-硅胶材料包括Na、K2Na和Na2K。
• Sulfur-Phenolate Exchange as a Mild, Fast, and High-Yielding Method toward the Synthesis of Sulfonamides
  作者：Alyssa F. J. van den Boom、Han Zuilhof

  DOI：10.1021/acs.orglett.2c04292

  日期：2023.2.10

  Sulfonamides have many important biological applications, yet their synthesis often involves long reaction times under dry and non-ambient conditions. Here we report the synthesis of a large range of sulfonamides at room temperature using 4-nitrophenyl benzylsulfonate as a starting material. Sulfonamides were prepared from a wide range of aliphatic, linear, and cyclic amines, anilines, and N-methylanilines

  磺酰胺具有许多重要的生物应用，但其合成通常需要在干燥和非环境条件下进行较长的反应时间。在这里，我们报道了使用 4-硝基苯基苄基磺酸盐作为起始材料在室温下合成多种磺酰胺。磺酰胺由多种脂肪族、直链和环状胺、苯胺和N-甲基苯胺制备。这里观察到的产率和反应时间与之前报道的相当或更好，确立了硫酚盐交换作为可行的替代方案。
• Palladium-catalysed arylation of sulfonamide stabilised enolates
  作者：Jacob G. Zeevaart、Christopher J. Parkinson、Charles B. de Koning

  DOI：10.1016/j.tetlet.2005.01.096

  日期：2005.3

  alpha-Arylation of inethanesulfonamides using palladium catalysis is described. For example, treatment of N-benzyl-Nmethylmethanesulfonamide with catalytic Pd(OAc)(2) in the presence of sodium tert-butoxide, triphenylphosphine and toluene afforded N-benzy]-N-methylphenylinethanesulfonamide in 66% yield. (C) 2005 Elsevier Ltd. All rights reserved.
• Martensson,O.; Nilsson,E., Acta Chemica Scandinavica (1947), 1960, vol. 14, p. 1151 - 1160
  作者：Martensson,O.、Nilsson,E.

  DOI：——

  日期：——