S-(tert-butyl)-N-methyl-N-phenylthiohydroxylamine | 65605-23-4

• 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: S-(tert-butyl)-N-methyl-N-phenylthiohydroxylamine
• 英文别名: N-tert-butylsulfanyl-N-methylaniline
• CAS: 65605-23-4
• 化学式: C₁₁H₁₇NS
• 分子量: 195.329
• InChiKey: APPSCEOCEVGGKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-(tert-butyl)-N-methyl-N-phenylthiohydroxylamine 以 甲苯 为溶剂， 340.0~390.0 ℃ 、1.73 kPa 条件下， 生成 异丁烷 、 异丁烯 、 mercapto-N-methyl-aniline 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Gas-phase thermolysis ofN-methyl-N-phenyl-tert-butylsulfenamide and morpholinyl-tert-butylsulfenamide

  摘要：

  N-Methyl-N-phenyl-tert-butylsulfenamide (MPSA) and morpholinyl-tert-butylsulfenamide (MOSA) were thermolyzed in a stirred-flow reactor at temperatures of 340-390 degrees C and pressures of 7-13 Torr, using toluene as carrier gas, at residence times of 0.3-1.3 s. Isobutene was formed in 99% yield through first-order reactions having the following Arrhenius parameters (A,s(-1), E-a, kJ mol(-1)): MPSA, log A = 12.41 +/- 0.02, E-a = 158.8 +/- 0.2; MOSA, log A = 12.91 +/- 0.22, E-a = 159 +/- 3. It is proposed that the elimination of isobutene takes place by unimolecular reaction mechanisms involving polar, four-center cyclic transition states, forming S-unsubstituted thiohydroxylamines as coproducts. Thermochemical parameters, estimated by semiempirical AM1 calculations, are reported for the latter and for the parent molecules. (C) 1998 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199806)11:6<407::aid-poc5>3.0.co;2-g
• 作为产物：
  描述：

  1,1-dimethylethanesulfenyl chloride 、 N-甲基苯胺 以40%的产率得到S-(tert-butyl)-N-methyl-N-phenylthiohydroxylamine
  参考文献：
  名称：

  Gas-phase thermolysis ofN-methyl-N-phenyl-tert-butylsulfenamide and morpholinyl-tert-butylsulfenamide

  摘要：

  N-Methyl-N-phenyl-tert-butylsulfenamide (MPSA) and morpholinyl-tert-butylsulfenamide (MOSA) were thermolyzed in a stirred-flow reactor at temperatures of 340-390 degrees C and pressures of 7-13 Torr, using toluene as carrier gas, at residence times of 0.3-1.3 s. Isobutene was formed in 99% yield through first-order reactions having the following Arrhenius parameters (A,s(-1), E-a, kJ mol(-1)): MPSA, log A = 12.41 +/- 0.02, E-a = 158.8 +/- 0.2; MOSA, log A = 12.91 +/- 0.22, E-a = 159 +/- 3. It is proposed that the elimination of isobutene takes place by unimolecular reaction mechanisms involving polar, four-center cyclic transition states, forming S-unsubstituted thiohydroxylamines as coproducts. Thermochemical parameters, estimated by semiempirical AM1 calculations, are reported for the latter and for the parent molecules. (C) 1998 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199806)11:6<407::aid-poc5>3.0.co;2-g

文献信息

• Using sulfinamides as high oxidation state sulfur reagent for preparation of sulfenamides
  作者：Long-jun Ma、Guang-xun Li、Jin Huang、Jin Zhu、Zhuo Tang

  DOI：10.1016/j.tetlet.2018.03.033

  日期：2018.4

  Traditional preparation of sulfenamides require the use of low oxidation state of sulfur reagent such as RSCl, (RS)2 or RSH, which are toxic, odorous and difficult to deal with due to the harsh reaction conditions. Here high oxidation state of sulfur reagent—aliphatic sulfinamide, were used for preparation of sulfenamide in one step efficiently. Different aromatic amines with all sorts of functional

  传统的次磺酰胺制剂需要使用低氧化态的硫试剂，例如RSCl，（RS）2或RSH，这些试剂有毒，有气味，并且由于苛刻的反应条件而难以处理。在这里，硫试剂-脂肪族亚磺酰胺的高氧化态一步有效地用于制备亚磺酰胺。具有各种官能团（尤其是氨基和羟基）的不同芳族胺以中等收率转化为相应的亚磺酰胺，这是以前方法很难获得的。
• Gas-phase thermolysis ofN-methyl-N-phenyl-tert-butylsulfenamide and morpholinyl-tert-butylsulfenamide
  作者：Gonzalo Martin、Julian Ascanio、Jesus Rodriguez

  DOI：10.1002/(sici)1099-1395(199806)11:6<407::aid-poc5>3.0.co;2-g

  日期：1998.6

  N-Methyl-N-phenyl-tert-butylsulfenamide (MPSA) and morpholinyl-tert-butylsulfenamide (MOSA) were thermolyzed in a stirred-flow reactor at temperatures of 340-390 degrees C and pressures of 7-13 Torr, using toluene as carrier gas, at residence times of 0.3-1.3 s. Isobutene was formed in 99% yield through first-order reactions having the following Arrhenius parameters (A,s(-1), E-a, kJ mol(-1)): MPSA, log A = 12.41 +/- 0.02, E-a = 158.8 +/- 0.2; MOSA, log A = 12.91 +/- 0.22, E-a = 159 +/- 3. It is proposed that the elimination of isobutene takes place by unimolecular reaction mechanisms involving polar, four-center cyclic transition states, forming S-unsubstituted thiohydroxylamines as coproducts. Thermochemical parameters, estimated by semiempirical AM1 calculations, are reported for the latter and for the parent molecules. (C) 1998 John Wiley & Sons, Ltd.