2-isopropenyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole | 177763-13-2

• 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: 2-isopropenyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole
• 英文别名: 2-isopropenyl-1-[(4-methylphenyl)sulfonyl]indoline；1H-Indole, 2,3-dihydro-2-(1-methylethenyl)-1-[(4-methylphenyl)sulfonyl]-；1-(4-methylphenyl)sulfonyl-2-prop-1-en-2-yl-2,3-dihydroindole
• CAS: 177763-13-2
• 化学式: C₁₈H₁₉NO₂S
• 分子量: 313.42
• InChiKey: ABBYKKRAEOZZOP-UHFFFAOYSA-N

物化性质

• 沸点：
  451.5±55.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(3-甲基丁-2-烯基)苯胺 在 吡啶 、 双氧水 、 silica gel 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 116.25h， 生成 2-isopropenyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole
  参考文献：
  名称：

  摘要：

  Cyclization of the carbamate of 2-(dimethylallyl)aniline with phenylselanyl chloride (benzeneselenenyl chloride) gave a 1:1 mixture of a dihydroindole and a tetrahydroquinoline. With phenylselanyl bromide only the dihydroindole was obtained. Addition of methanol to the silica used in the procedure trapped the reaction at the non-cyclized stage forming a 3-methoxy-3-methyl-2-(phenylselanyl)butyl side chain. The sulfonamide of 2-(dimethylallyl)aniline only formed the dihydroindole with phenylselanyl chloride. The corresponding trifluoroacetamide derivative did not form any cyclized product under the same conditions. The dihydroindole could be converted into the corresponding alkene by oxidative removal of the phenylseleno group. 4-Ethoxycarbonyl-2-(3,3-dimethylallyl)aniline cyclized with mercuric nitrate to give, after a reductive workup, a 2,2-dimethyltetrahydroquinoline. The X-ray crystal structures of ethyl N-{2-[3-methoxy-3-methyl-2-(phenylselanyl)butyl] phenyl} carbamate and 2-[1-methyl-1-(phenylselanyl)ethyl]-1-[(4-methylphenyl)sulfonyl]indoline are reported.

  DOI：

  10.1071/ch99109

文献信息

• Aerobic Intramolecular Oxidative Amination of Alkenes Catalyzed by NHC-Coordinated Palladium Complexes
  作者：Michelle M. Rogers、Johanna E. Wendlandt、Ilia A. Guzei、Shannon S. Stahl

  DOI：10.1021/ol060327q

  日期：2006.5.1

  [reaction: see text] Palladium(II) complexes bearing a single N-heterocyclic carbene ligand serve as effective catalysts for the aerobic oxidative cyclization of alkenes with pendant sulfonamides. The use of carboxylic acid cocatalysts (AcOH and PhCO(2)H) often leads to significant improvements in catalyst stability and product yield and enables catalytic turnover to be achieved with air, rather than

  [反应：见正文]带有单个N-杂环卡宾配体的钯（II）配合物可作为有效的催化剂，对带有侧基磺酰胺的烯烃进行好氧氧化环化。羧酸助催化剂（AcOH和PhCO（2）H）的使用通常会显着提高催化剂的稳定性和产品收率，并使空气（而不是纯氧气）作为O（2）的来源实现催化转化。 。
• Acceptorless dehydrogenative amination of alkenes for the synthesis of N-heterocycles
  作者：Jia-Lin Tu、Wan Tang、Shi-Hui He、Ma Su、Feng Liu

  DOI：10.1007/s11426-022-1241-x

  日期：2022.7

  Catalytic amination of alkenes is one of the most attractive reactions for the construction of complex heterocycles with nitrogen centers. Herein, we present that synergistic photoredox and cobaloxime catalysis allows for highly efficient and mild dehydrogenative reactions between various NH nucleophiles and di-, tri-, and tetrasubstituted alkenes in the absence of external oxidants, thus enabling

  烯烃的催化胺化是构建具有氮中心的复杂杂环最有吸引力的反应之一。在这里，我们提出协同光氧化还原和钴肟催化允许在没有外部氧化剂的情况下，各种 NH 亲核试剂与二、三和四取代烯烃之间进行高效和温和的脱氢反应，从而能够获得一系列N杂环。值得注意的是，含Z和E烯烃的N杂环都是可以得到的。机理研究表明Z-肉桂基衍生物可以通过光催化E to Z通过能量转移过程进行烯烃异构化。此外，我们发现缓慢的能量转移可以抑制E到Z烯烃异构化过程，从而提供具有E选择性的肉桂基衍生物。我们的结果突出了使用双光氧化还原和钴肟催化反应产生多种N-杂环的好处。
• Pd-Catalyzed Regioselective Intramolecular Allylic C–H Amination of 1,1-Disubstituted Alkenyl Amines
  作者：Young Ho Kim、Dong Bin Kim、Su San Jang、So Won Youn

  DOI：10.1021/acs.joc.2c00781

  日期：2022.6.3

  Pd-Catalyzed intramolecular allylic C–H amination of 1,1-disubstituted alkenyl amines with various allylic tethers (X = O, NMs, CH2) was developed. This process allows for the divergent synthesis of 1,3-X,N-heterocycles through a regioselective allylic C–H cleavage and π-allylpalladium formation. Particularly noteworthy is the use of substrates containing a labile allylic moiety and new simple catalytic

  开发了 Pd 催化的 1,1-二取代烯基胺与各种烯丙基链 (X = O, NMs, CH 2 ) 的分子内烯丙基 C-H 胺化。该过程允许通过区域选择性烯丙基 C-H 裂解和 π-烯丙基钯形成来不同地合成 1,3- X、N-杂环。特别值得注意的是使用含有不稳定烯丙基部分的底物和新的简单催化系统，能够通过克服重大挑战来促进高度化学和区域选择性的烯丙基 C-H 胺化。
• Palladium(II)-Catalyzed Cyclization of Olefinic Tosylamides
  作者：Richard C. Larock、Timothy R. Hightower、Lisa A. Hasvold、Karl P. Peterson

  DOI：10.1021/jo952088i

  日期：1996.1.1
• Pd-Catalyzed Heteroannulation Using <i>N</i>-Arylureas as a Sterically Undemanding Ligand Platform
  作者：Jakub Vaith、Dasha Rodina、Gregory C. Spaulding、Shauna M. Paradine

  DOI：10.1021/jacs.2c01019

  日期：2022.4.20