N-allyl-N-(allylthio)-4-methylbenzenesulfonamide | 10330-28-6

• 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-allyl-N-(allylthio)-4-methylbenzenesulfonamide
• 英文别名: N-Allyl-N-allylthio-p-tolylsulfonylsulfilimine；4-methyl-N-prop-2-enyl-N-prop-2-enylsulfanylbenzenesulfonamide
• CAS: 10330-28-6
• 化学式: C₁₃H₁₇NO₂S₂
• 分子量: 283.415
• InChiKey: IXIBMYHQBBPCFG-UHFFFAOYSA-N

物化性质

• 熔点：
  74.5-75.5 °C
• 沸点：
  388.2±52.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二烯丙基硫醚 、 [(N-tosylimino)iodo]benzene 在 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以82%的产率得到N-allyl-N-(allylthio)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Novel asymmetric catalytic synthesis of sulfimides

  摘要：

  前手性硫化物在催化量的CuI盐和手性4,4'-二取代双(噁唑啉)配体的存在下与PhINTs反应，生成相应的手性硫酰胺。

  DOI：

  10.1039/cc9960000931

文献信息

• Novel asymmetric catalytic synthesis of sulfimides
  作者：Hiroya Takada、Yoshiaki Nishibayashi、Kouichi Ohe、Sakae Uemura

  DOI：10.1039/cc9960000931

  日期：——

  Prochiral sulfides react with PhINTs in the presence of a catalytic amount of CuI salt together with chiral 4,4′-disubstituted bis(oxazoline) ligands to afford the corresponding chiral sulfimides.

  前手性硫化物在催化量的CuI盐和手性4,4'-二取代双(噁唑啉)配体的存在下与PhINTs反应，生成相应的手性硫酰胺。
• Catalytic Asymmetric Sulfimidation
  作者：Hiroya Takada、Yoshiaki Nishibayashi、Kouichi Ohe、Sakae Uemura、Charlotte P. Baird、Tim J. Sparey、Paul C. Taylor

  DOI：10.1021/jo970798d

  日期：1997.9.1

  A direct catalytic imidation of sulfides to sulfimides with [N-(p-tolylsulfonyl)imino]phenyliodinane (TsN=IPh) using a catalytic amount of copper triflate (CuOTf) has been developed. The reaction proceeds with a wide range of sulfides to give the corresponding sulfimides in 50-83% isolated yields. When the reaction is applied to allylic sulfides, the products are the corresponding sulfonamides produced via [2,3] sigmatropic rearrangement of the initially formed allylic sulfimides. In the presence of a chiral bis(oxazoline) as ligand, asymmetric induction occurs to afford the chiral sulfimides (up to 71% ee) and sulfonamides (up to 58% ee). Chloramine T (TsNClNa) can be used in place of TsN=IPh for asymmetric sulfimidation, but the ee's are much lower. Some mechanistic observations are described.
• Imino‐λ ³ ‐iodane and Catalytic Amount of I ₂ ‐Mediated Synthesis of <i>N</i> ‐Allylsulfenamides via [2,3]‐Sigmatropic Rearrangement
  作者：Cody L. Makitalo、Akira Yoshimura、Gregory T. Rohde、Irina A. Mironova、Rosa Y. Yusubova、Mekhman S. Yusubov、Viktor V. Zhdankin、Akio Saito

  DOI：10.1002/ejoc.202000961

  日期：2020.11.8

  Imino‐λ3‐iodane and catalytic I2‐mediated facile metal‐free [2,3]‐sigmatropic rearrangement reaction of allyl sulfides producing N‐allysulfenamiides has been developed

  亚氨基λ 3 -iodane和催化我2介导的容易的不含金属的[2,3] -sigmatropic重排烯丙基硫化物产生的反应Ñ -allysulfenamiides已经开发