o-isoprenyl-N-methanesulfonylanilide | 918297-94-6

• 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: o-isoprenyl-N-methanesulfonylanilide
• 英文别名: N-(2-(prop-1-en-2-yl)phenyl)methanesulfonamide；N-[2-(Prop-1-en-2-yl)phenyl]methanesulfonamide；N-(2-prop-1-en-2-ylphenyl)methanesulfonamide
• CAS: 918297-94-6
• 化学式: C₁₀H₁₃NO₂S
• 分子量: 211.285
• InChiKey: LMGGEMKSUZIIKL-UHFFFAOYSA-N

物化性质

• 沸点：
  328.4±35.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  o-isoprenyl-N-methanesulfonylanilide 在 二苯硒醚 、 tetrabutylammonium tetrafluoroborate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以48%的产率得到3-methyl-1-(methylsulfonyl)-1H-indole
  参考文献：
  名称：

  2-乙烯基苯胺的硒电催化环化对肽标记的吲哚

  摘要：

  可持续的硒电催化方法实现了 2-乙烯基苯胺的分子内环化，用于在极其温和的条件下合成具有肽标记的修饰吲哚

  DOI：

  10.1002/asia.202200762
• 作为产物：
  描述：

  1-硝基-2-丙-1-烯-2-基苯 在 sodium thiosulfate 作用下， 生成 o-isoprenyl-N-methanesulfonylanilide
  参考文献：
  名称：

  Novel formation of indoles and 3,1-benzoxazines from o-alkenylanilides and dimethyl(methylthio)sulfonium trifluoromethanesulfonate

  摘要：

  The reaction of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) with o-allylphenol gave 2-methylthiomethyl-2,3-dihydrobenzofuran in 97% yield. The reaction of DMTST with N-tosyl-o-isopropenylanilide followed by the addition of aq sodium carbonate afforded N-tosyl-3-methylindole in 88% yield, whereas N-tosyl-o-vinylanilide afforded N-tosylindoline in 85% yield. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.05.111

文献信息

• Regioselective Synthesis of Benzazetines and Indoles from Alkenylanilides and Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate
  作者：Kentaro Okuma、Itsuki Takeshita、Takumi Yasuda、Kosei Shioji

  DOI：10.1246/cl.2006.1122

  日期：2006.10

  Regioselective synthesis of benzazetines and indoles from o-alkenylanilides was achieved. The reaction of o-vinylbenzanilide with dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) gave the corresponding benzazetine in 92% yield, whereas the reaction of o-vinyl-N-p-toluenesulfonylanilide gave N-tosylindoline in 77% yield. 3-Methy-N-p-tosylindole was directly synthesized by the reaction of o-isopropenyl-N-p-tosylanilide with dimethyl disulfide and methyl triflate in 85% yield.

  实现了从邻烯基苯胺酸酯选择性合成苯并吖庚因和吲哚。邻乙烯基苯并苯胺酸酯与二甲基（甲硫基）硫镨三氟甲磺酸盐（DMTST）反应得到相应苯并吖庚因，产率达92%；而邻乙烯基-N-对甲苯磺酰苯胺酸酯反应得到N-对甲苯磺酰吲哚啉，产率达77%。通过邻异丙烯基-N-对甲苯磺酰苯胺酸酯与二甲基二硫和甲基三氟甲磺酸盐反应，可直接合成3-甲基-N-对甲苯磺酰吲哚，产率达85%。
• Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinyl­anilines with O2 as Terminal Oxidant and TEMPO as Cocatalyst
  作者：Sherry Chemler、Timothy Liwosz

  DOI：10.1055/s-0034-1379015

  日期：——

  A copper-catalyzed intramolecular alkene oxidative amination that utilizes TEMPO as co-catalyst and O₂ as the terminal oxidant has been developed. The method furnishes N-aryl and N-sulfonyl indoles from N-aryl and N-sulfonyl 2-vinylanilines, respectively. Additionally, sequential copper-catalyzed reactions where initial Chan-Lam coupling of 2-vinylanilines with arylboronic acids is followed by oxidative amination of the alkene can generate N-aryl indoles in one pot.
• Novel formation of indoles and 3,1-benzoxazines from o-alkenylanilides and dimethyl(methylthio)sulfonium trifluoromethanesulfonate
  作者：Kentaro Okuma、Takumi Yasuda、Itsuki Takeshita、Kosei Shioji、Yoshinobu Yokomori

  DOI：10.1016/j.tet.2007.05.111

  日期：2007.8

  The reaction of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) with o-allylphenol gave 2-methylthiomethyl-2,3-dihydrobenzofuran in 97% yield. The reaction of DMTST with N-tosyl-o-isopropenylanilide followed by the addition of aq sodium carbonate afforded N-tosyl-3-methylindole in 88% yield, whereas N-tosyl-o-vinylanilide afforded N-tosylindoline in 85% yield. (c) 2007 Published by Elsevier Ltd.
• Selenium‐Electrocatalytic Cyclization of 2‐Vinylanilides towards Indoles of Peptide Labeling
  作者：Shaogao Zeng、Songlin Fang、Haiping Cai、Dong Wang、Weiliang Liu、Xinwei Hu、Pinghua Sun、Zhixiong Ruan

  DOI：10.1002/asia.202200762

  日期：2022.10.17

  The sustainable selenium-electrocatalytic approach enabled intramolecular cyclization of 2-vinylanilides for versatile syntheses of decorated indoles with peptide labelling under exceedingly mild conditions

  可持续的硒电催化方法实现了 2-乙烯基苯胺的分子内环化，用于在极其温和的条件下合成具有肽标记的修饰吲哚