1,1,3,3-tetramethylguanidine p-toluenesulfonate | 321709-95-9

• 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: 1,1,3,3-tetramethylguanidine p-toluenesulfonate
• 英文别名: 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfonate；4-methylbenzenesulfonic acid 1,1,3,3-tetramethylguanidine salt；[TMG][TsO]；4-Methylbenzenesulfonic acid;1,1,3,3-tetramethylguanidine
• CAS: 321709-95-9
• 化学式: C₅H₁₃N₃*C₇H₈O₃S
• 分子量: 287.383
• InChiKey: CGCAARSAQXRJAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-methylbenzenesulfinic acid 1,1,3,3-tetramethylguanidine salt 在 氧气 作用下， 反应 72.0h， 生成 1,1,3,3-tetramethylguanidine p-toluenesulfonate
  参考文献：
  名称：

  A solid-state oxidation of 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfinate to 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfonate

  摘要：

  通过在空气中进行固态氧化，从相应的 1,1,3,3- 四甲基胍 4-甲基苯磺酸络合物 C5H14N3+-C7H7O3S- 中得到了有机酸碱络合物 1,1,3,3- 四甲基胍 4-甲基苯磺酸络合物 C5H14N3+-C7H7O2S-。比较两种晶体结构发现，它们在单斜空间群 P21/c 中具有相似的堆积排列，中心对称的 2:2 四聚体由两个 1,1,3,3 四甲基胍碱的亚胺 N 原子和两个酸分子的 O 原子之间的四个强 N-H...O=S 氢键连接。

  DOI：

  10.1107/s0108270113015011
• 作为试剂：
  描述：

  环己酮肟 在 1,1,3,3-tetramethylguanidine p-toluenesulfonate 、 对甲苯磺酰氯 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以98%的产率得到己内酰胺
  参考文献：
  名称：

  A mild and efficient way to prepare ε-caprolactam by using a novel salt related with ionic liquids

  摘要：

  The Beckmann rearrangement of several ketoximes has been performed by treatment with tosyl chloride, using ionic liquids as both solvent and catalyst, without the need of any other promoter. High levels of conversion and selectivity were observed in the majority of experiments. Work-up is very simple and the product can be isolated in high yields. When the method was applied to cyclohexanone oxime, the novel salt [TMG][TsO] instead of the ionic liquid was used. This procedure afforded a conversion of 100% to obtain pure epsilon-caprolactam in a 98% yield. [TMG][TsO] is easy to prepare, cheap, and not corrosive. It can be recovered and reused. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.145

文献信息

• A mild and efficient way to prepare ε-caprolactam by using a novel salt related with ionic liquids
  作者：Miguel Vilas、Emilia Tojo

  DOI：10.1016/j.tetlet.2010.05.145

  日期：2010.8

  The Beckmann rearrangement of several ketoximes has been performed by treatment with tosyl chloride, using ionic liquids as both solvent and catalyst, without the need of any other promoter. High levels of conversion and selectivity were observed in the majority of experiments. Work-up is very simple and the product can be isolated in high yields. When the method was applied to cyclohexanone oxime, the novel salt [TMG][TsO] instead of the ionic liquid was used. This procedure afforded a conversion of 100% to obtain pure epsilon-caprolactam in a 98% yield. [TMG][TsO] is easy to prepare, cheap, and not corrosive. It can be recovered and reused. (C) 2010 Elsevier Ltd. All rights reserved.
• A solid-state oxidation of 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfinate to 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfonate
  作者：Åsmund Kaupang、Carl Henrik Görbitz、Tore Bonge-Hansen

  DOI：10.1107/s0108270113015011

  日期：2013.7.15

  The organic acid–base complex 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfonate, C₅H₁₄N₃⁺·C₇H₇O₃S⁻, was obtained from the corresponding 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfinate complex, C₅H₁₄N₃⁺·C₇H₇O₂S⁻, by solid-state oxidation in air. Comparison of the two crystal structures reveals similar packing arrangements in the monoclinic space groupP2₁/c, with centrosymmetric 2:2 tetramers being connected by four strong N—H...O=S hydrogen bonds between the imine N atoms of two 1,1,3,3-tetramethylguanidinium bases and the O atoms of two acid molecules.

  通过在空气中进行固态氧化，从相应的 1,1,3,3- 四甲基胍 4-甲基苯磺酸络合物 C5H14N3+-C7H7O3S- 中得到了有机酸碱络合物 1,1,3,3- 四甲基胍 4-甲基苯磺酸络合物 C5H14N3+-C7H7O2S-。比较两种晶体结构发现，它们在单斜空间群 P21/c 中具有相似的堆积排列，中心对称的 2:2 四聚体由两个 1,1,3,3 四甲基胍碱的亚胺 N 原子和两个酸分子的 O 原子之间的四个强 N-H...O=S 氢键连接。