2-methyl-N-(p-tolyl)propane-2-sulfonamide | 1305205-30-4

• 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: 2-methyl-N-(p-tolyl)propane-2-sulfonamide
• 英文别名: 2-methyl-N-(4-methylphenyl)propane-2-sulfonamide
• CAS: 1305205-30-4
• 化学式: C₁₁H₁₇NO₂S
• 分子量: 227.327
• InChiKey: AOCVUUUKUZGPIN-UHFFFAOYSA-N

物化性质

• 熔点：
  147.2-149.2 °C
• 沸点：
  329.7±35.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲酚 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 2-甲基-2-丁醇 、 乙腈 为溶剂， 反应 15.0h， 生成 2-methyl-N-(p-tolyl)propane-2-sulfonamide
  参考文献：
  名称：

  A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates

  摘要：

  A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO4 in tert-amyl alcohol was found to be the optimal base solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.

  DOI：

  10.1021/jo200443u

文献信息

• PHOSPHINE LIGANDS FOR CATALYTIC REACTIONS
  申请人：AbbVie Inc.

  公开号：US20160263566A1

  公开（公告）日：2016-09-15

  The disclosure is directed to: (a) phosphacycle ligands; (b) catalyst compositions comprising phosphacycle ligands; and (c) methods of using such phosphacycle ligands and catalyst compositions in bond forming reactions.

  本公开涉及：(a) 磷杂环配体；(b) 包含磷杂环配体的催化剂组合物；以及(c) 使用这些磷杂环配体和催化剂组合物在化学键形成反应中的方法。
• Copper-catalyzed N-arylation of sulfonamides with aryl bromides under mild conditions
  作者：Xiang Wang、Anil Guram、Michael Ronk、Jacqueline E. Milne、Jason S. Tedrow、Margaret M. Faul

  DOI：10.1016/j.tetlet.2011.10.113

  日期：2012.1

  This Letter describes a copper catalyzed sulfonamide coupling reaction with aryl bromides to form N-aryl sulfonamides under mild conditions, including the first examples of Cu-catalyzed sulfonamide coupling at room temperature. The reaction protocol tolerates a broad range of substrates including a variety of primary and secondary sulfonamides and challenging heteroaryl bromides such as 2-bromothiazole. (C) 2011 Elsevier Ltd. All rights reserved.
• US7943639B2
  申请人：——

  公开号：US7943639B2

  公开（公告）日：2011-05-17
• US9381508B2
  申请人：——

  公开号：US9381508B2

  公开（公告）日：2016-07-05
• US9669399B2
  申请人：——

  公开号：US9669399B2

  公开（公告）日：2017-06-06