N-(o-nitrobenzenesulfonyl)-1,2,3,4-tetrahydroquinoline | 24223-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(o-nitrobenzenesulfonyl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 1-(2-nitro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline；1-(2-nitrophenyl)sulfonyl-3,4-dihydro-2H-quinoline
• CAS: 24223-38-9
• 化学式: C₁₅H₁₄N₂O₄S
• mdl: MFCD00577622
• 分子量: 318.353
• InChiKey: QJYQBYCCIMJSSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(o-nitrobenzenesulfonyl)-3-(o-iodophenyl)propylamine 在 copper(l) iodide 、 cesium acetate 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 4.0h， 以99%的产率得到N-(o-nitrobenzenesulfonyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  轻度的分子间和分子内芳基卤化胺与CuI和CsOAc的组合

  摘要：

  发现CuI和CsOAc的独特组合在温和条件下催化芳基胺化。该反应在室温或90°C下进行，具有广泛的官能团相容性。分子内反应能够形成在氮原子上具有各种保护基的五元，六元和七元环。研究了分子间胺化的范围及其在不对称的N，N'-二烷基化苯二胺上的应用。

  DOI：

  10.1016/j.tet.2008.09.042

文献信息

• Study on Radical Amidation onto Aromatic Rings with (Diacyloxyiodo)arenes
  作者：Hideo Togo、Yoichiro Hoshina、Takahito Muraki、Hiromasa Nakayama、Masataka Yokoyama

  DOI：10.1021/jo980450y

  日期：1998.7.1

  Sulfonamides of primary amines bearing an aromatic ring at the gamma-position were treated with (diacyloxyiodo)arenes and:iodine under irradiation conditions with;a tungsten-lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields. Here, the reactivity depends on the Z-group (protecting group) of the starting amides. Under the same reaction conditions, some sulfonamides were treated with (diacetoxyiodo)benzene and iodine in the presence of aromatics to give the corresponding N-arylated amides. These reactions proceed through the intramolecular and intermolecular amidations onto aromatic rings via the sulfonamidyl radicals formed.
• AN INTRAMOLECULAR AMINATION OF ARYL HALIDES WITH A COMBINATION OF COPPER (I) IODIDE AND CESIUM ACETATE: PREPARATION OF 5,6-DIMETHOXYINDOLE-1,2-DICARBOXYLIC ACID 1-BENZYL ESTER 2-METHYL ESTER
  作者：Noji, Toshiharu、Okano, Kentaro、Fukuyama, Tohru、Tokuyama, Hidetoshi

  DOI：10.15227/orgsyn.088.0388

  日期：——
• A mild inter- and intramolecular amination of aryl halides with a combination of CuI and CsOAc
  作者：Tetsuji Kubo、Chiharu Katoh、Ken Yamada、Kentaro Okano、Hidetoshi Tokuyama、Tohru Fukuyama

  DOI：10.1016/j.tet.2008.09.042

  日期：2008.12

  combination of CuI and CsOAc was found to catalyze aryl amination under mild conditions. The reaction takes place at room temperature or at 90 °C with broad functional group compatibility. The intramolecular reaction was able to form five-, six-, and seven-membered rings with various protecting groups on the nitrogen atom. The scope of the intermolecular amination, as well as its applications to unsymmetrical

  发现CuI和CsOAc的独特组合在温和条件下催化芳基胺化。该反应在室温或90°C下进行，具有广泛的官能团相容性。分子内反应能够形成在氮原子上具有各种保护基的五元，六元和七元环。研究了分子间胺化的范围及其在不对称的N，N'-二烷基化苯二胺上的应用。