Methyl 2-[(2,6-dimethylphenyl)sulfamoyl]acetate | 1136056-27-3

• 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: Methyl 2-[(2,6-dimethylphenyl)sulfamoyl]acetate
• CAS: 1136056-27-3
• 化学式: C₁₁H₁₅NO₄S
• 分子量: 257.31
• InChiKey: OQWKWIXTLOBSKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-[(2,6-dimethylphenyl)sulfamoyl]acetate 、 1,2-二溴乙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到Methyl 2-(2,6-dimethylphenyl)-1,1-dioxo-1,2-thiazolidine-5-carboxylate
  参考文献：
  名称：

  通过（烷氧基羰基甲烷）磺酰苯胺环烷基化合成阿马酸

  摘要：

  (Methoxycarbonylmethane)sulfonanilides are alkylated by alpha, omega-dihaloalkanes in K(2)CO(3)-DMF with the formation of sultams. A high sensitivity has been detected for the reaction rate on the electronic effect of substituents in the aromatic nucleus, although substituents in the ortho position do not obstruct the reaction and in the case of 2,6-disubstituted derivatives the reaction rate and sultam yield were maximal. Tertiary sulfonamides form derivatives of 1-sulfamoylcyclopropanecarboxylic acid under these conditions.

  DOI：

  10.1007/s10593-008-0066-9
• 作为产物：
  描述：

  2-(氯磺酰基)乙酸甲酯 、 2,6-二甲基苯胺 在 吡啶 作用下， 以 乙腈 为溶剂， 以82%的产率得到Methyl 2-[(2,6-dimethylphenyl)sulfamoyl]acetate
  参考文献：
  名称：

  通过（烷氧基羰基甲烷）磺酰苯胺环烷基化合成阿马酸

  摘要：

  (Methoxycarbonylmethane)sulfonanilides are alkylated by alpha, omega-dihaloalkanes in K(2)CO(3)-DMF with the formation of sultams. A high sensitivity has been detected for the reaction rate on the electronic effect of substituents in the aromatic nucleus, although substituents in the ortho position do not obstruct the reaction and in the case of 2,6-disubstituted derivatives the reaction rate and sultam yield were maximal. Tertiary sulfonamides form derivatives of 1-sulfamoylcyclopropanecarboxylic acid under these conditions.

  DOI：

  10.1007/s10593-008-0066-9

文献信息

• Straightforward Route to γ-Sultams via Novel Tandem SN/Michael Addition
  作者：Olga Bakulina、Anastasiia Klochkova、Andrey Bubyrev、Dmitry Dar’in、Mikhail Krasavin、Viktor Sokolov

  DOI：10.1055/a-1343-9451

  日期：2021.5

  A novel tandem approach to trisubstituted γ-sultams has been developed involving N-alkylation of methanesulfonanilides with EWG-substituted allyl bromides followed by intramolecular Michael addition. A series of various isothiazolidine 1,1-dioxides have been prepared under mild transition-metal-free conditions in high yields and trans-diastereoselectivity (confirmed by X-ray crystallography). The dependence

  已经开发出一种新颖的串联三取代的γ-sultams方法，包括用EWG取代的烯丙基溴对甲磺酰苯胺进行N-烷基化，然后进行分子内迈克尔加成。已在温和的无过渡金属条件下以高收率和反式非对映选择性（由X射线晶体学证实）制备了一系列各种异噻唑烷1,1-二氧化物。已经研究了反应性对基材的电子性能的依赖性。
• Synthesis of sultams by cycloalkylation of (alkoxycarbonylmethane)sulfonanilides
  作者：V. A. Rassadin、A. A. Tomashevskii、V. V. Sokolov、A. A. Potekhin

  DOI：10.1007/s10593-008-0066-9

  日期：2008.4

  (Methoxycarbonylmethane)sulfonanilides are alkylated by alpha, omega-dihaloalkanes in K(2)CO(3)-DMF with the formation of sultams. A high sensitivity has been detected for the reaction rate on the electronic effect of substituents in the aromatic nucleus, although substituents in the ortho position do not obstruct the reaction and in the case of 2,6-disubstituted derivatives the reaction rate and sultam yield were maximal. Tertiary sulfonamides form derivatives of 1-sulfamoylcyclopropanecarboxylic acid under these conditions.