N-(2-methyl-2-phenylpropyl)toluene-4-sulfonamide | 117583-61-6

• 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: N-(2-methyl-2-phenylpropyl)toluene-4-sulfonamide
• 英文别名: 4-methyl-N-(2-methyl-2-phenylpropyl)benzenesulfonamide
• CAS: 117583-61-6
• 化学式: C₁₇H₂₁NO₂S
• 分子量: 303.425
• InChiKey: LUVFCZABWGDGNN-UHFFFAOYSA-N

物化性质

• 沸点：
  442.7±48.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  N-亚硫酰基-p-甲苯磺胺 、 2-甲基-2-丙烯-1-醇 在 三氟化硼乙醚 作用下， 以 苯 为溶剂， 反应 12.0h， 以26%的产率得到N-(2-methyl-2-phenylpropyl)toluene-4-sulfonamide
  参考文献：
  名称：

  Convenient Syntheses of Chiral Cyclic Sulfinates (Sultines) from Unsaturated Alcohols

  摘要：

  The reaction of unsaturated alcohols with N-sulfinyl-p-toluenesulfonamide (TsNSO) is shown to lead stereoselectively to chiral cyclic or bicyclic sulfinates (sultines). The reactions occur at ambient temperatures and afford a general route to delta- and epsilon-sultines which are notable for their crystallinity and thermal stability. These studies confirm the preservation of stereochemical integrity of the carbon atom alpha to the oxygen atom in the sultine ring. Some unsaturated aldehydes furnish sultines via a tandem oxo-ene cyclization and subsequent ring closure to the sultine. In some reactions, N-toluenesulfonamide derivatives of sultines (compounds of type 11) were isolated, and since those were converted into the sultines by the action of BF3-OEt(2), such sulfonamides are considered to be intermediates in the reaction pathway.

  DOI：

  10.1021/jo00129a056

文献信息

• Fast Titanium‐Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine
  作者：Jens Bielefeld、Sven Doye

  DOI：10.1002/anie.202001111

  日期：2020.4.6

  The scientific interest in catalytic hydroaminoalkylation reactions of alkenes has vastly increased over the past decade, but these reactions have struggled to become a viable option for general laboratory or industrial use because of reaction times of several days. The titanium-based catalytic system introduced in this work not only reduces the reaction time by several orders of magnitude, into the

  在过去的十年中，人们对烯烃催化加氢氨基烷基化反应的科学兴趣大大增加，但由于反应时间长达数天，这些反应一直难以成为一般实验室或工业用途的可行选择。这项工作中引入的钛基催化系统不仅将反应时间缩短了几个数量级，达到几分钟的范围，而且该催化剂也被证明可以很容易地从普通起始材料中获得，成本约为 1 欧元每毫摩尔催化剂。我们还能够正式对甲胺进行 CH 活化，并通过胺的甲硅烷基保护和简单的水脱保护实现与多种烯烃的偶联。
• STAMM, HELMUT;ONISTSCHENKO, ANDREAS;BUCHHOLZ, BERTHOLD;MALL, THOMAS, J. ORG. CHEM., 54,(1989) N, C. 193-199
  作者：STAMM, HELMUT、ONISTSCHENKO, ANDREAS、BUCHHOLZ, BERTHOLD、MALL, THOMAS

  DOI：——

  日期：——
• Convenient Syntheses of Chiral Cyclic Sulfinates (Sultines) from Unsaturated Alcohols
  作者：Charles M. Marson、Paul R. Giles

  DOI：10.1021/jo00129a056

  日期：1995.12

  The reaction of unsaturated alcohols with N-sulfinyl-p-toluenesulfonamide (TsNSO) is shown to lead stereoselectively to chiral cyclic or bicyclic sulfinates (sultines). The reactions occur at ambient temperatures and afford a general route to delta- and epsilon-sultines which are notable for their crystallinity and thermal stability. These studies confirm the preservation of stereochemical integrity of the carbon atom alpha to the oxygen atom in the sultine ring. Some unsaturated aldehydes furnish sultines via a tandem oxo-ene cyclization and subsequent ring closure to the sultine. In some reactions, N-toluenesulfonamide derivatives of sultines (compounds of type 11) were isolated, and since those were converted into the sultines by the action of BF3-OEt(2), such sulfonamides are considered to be intermediates in the reaction pathway.