2-(p-toluenesulfinyl)acetamide | 1025507-95-2

• 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-(p-toluenesulfinyl)acetamide
• 英文别名: 2-(4-Methylphenyl)sulfinylacetamide；2-(4-methylphenyl)sulfinylacetamide
• CAS: 1025507-95-2
• 化学式: C₉H₁₁NO₂S
• mdl: MFCD20547553
• 分子量: 197.258
• InChiKey: PZJDXNUEDAWALN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-甲基苯基)硫基乙酰胺 在 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以2.52 g的产率得到2-(p-toluenesulfinyl)acetamide
  参考文献：
  名称：

  Nitrilase-catalysed hydrolysis of cyanomethyl p-tolyl sulfoxide: stereochemistry and mechanism

  摘要：

  Several commercially available nitrilases have been used for the enantioselective hydrolysis of cyanomethyl p-tolyl sulfoxide into the corresponding amide and acid, which are formed in different proportions and with varying stereo selectivities, depending on the nitrilase involved. It was shown that the externally added amide is not transformed into the acid, which can be explained by assuming that both products must be produced in concurrent reactions. It was also demonstrated that the absolute configuration of the substrate exerts substantial influence on the product ratio. Two alternative explanations of the stereochemical course are presented. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.021

文献信息

• Nitrilase-catalysed hydrolysis of cyanomethyl p-tolyl sulfoxide: stereochemistry and mechanism
  作者：Piotr Kiełbasiński、Michał Rachwalski、Marian Mikołajczyk、Floris P.J.T. Rutjes

  DOI：10.1016/j.tetasy.2008.01.021

  日期：2008.3

  Several commercially available nitrilases have been used for the enantioselective hydrolysis of cyanomethyl p-tolyl sulfoxide into the corresponding amide and acid, which are formed in different proportions and with varying stereo selectivities, depending on the nitrilase involved. It was shown that the externally added amide is not transformed into the acid, which can be explained by assuming that both products must be produced in concurrent reactions. It was also demonstrated that the absolute configuration of the substrate exerts substantial influence on the product ratio. Two alternative explanations of the stereochemical course are presented. (C) 2008 Elsevier Ltd. All rights reserved.