2,3,4,5-tetrahydro-2-[(4-methylphenyl)sulfonyl]-1H-2-benzazepin-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 2,3,4,5-tetrahydro-2-[(4-methylphenyl)sulfonyl]-1H-2-benzazepin-1-one
• 英文别名: 2-(4-methylphenyl)sulfonyl-4,5-dihydro-3H-2-benzazepin-1-one
• 化学式: C₁₇H₁₇NO₃S
• 分子量: 315.393
• InChiKey: XRAYIYHJVOPYHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  五氟苯甲醛 、 N-[(4-甲基苯基)磺酰基]-3-(2-溴苯基)丙胺 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,3-双(二苯基膦)丙烷 、 potassium carbonate 作用下， 以 xylene 为溶剂， 反应 48.0h， 以66%的产率得到2,3,4,5-tetrahydro-2-[(4-methylphenyl)sulfonyl]-1H-2-benzazepin-1-one
  参考文献：
  名称：

  Rhodium-Catalyzed Intramolecular Aminocarbonylation of Aryl Halides Using Aldehydes as a Source of Carbon Monoxide

  摘要：

  在催化量的铑络合物存在下，N-Ts-(2-溴苯基)烷基胺与醛反应会导致芳基卤化物的分子内氨基羰基化，生成五元、六元和七元的苯并内酰胺。

  DOI：

  10.1246/cl.2003.154

文献信息

• Rhodium-Catalyzed Intramolecular Aminocarbonylation of Aryl Halides Using Aldehydes as a Source of Carbon Monoxide
  作者：Tsumoru Morimoto、Masahiko Fujioka、Koji Fuji、Ken Tsutsumi、Kiyomi Kakiuchi

  DOI：10.1246/cl.2003.154

  日期：2003.2

  The reaction of N-Ts-(2-bromophenyl)alkylamines with aldehydes in the presence of a catalytic amount of a rhodium complex results in the intramolecular aminocarbonylation of the aryl halides to give five-, six-, and seven-membered benzolactams.

  在催化量的铑络合物存在下，N-Ts-(2-溴苯基)烷基胺与醛反应会导致芳基卤化物的分子内氨基羰基化，生成五元、六元和七元的苯并内酰胺。
• Visible-light induced generation of bifunctional nitrogen-centered radicals: a concise synthetic strategy to construct bicyclo[3.2.1] octane and azepane cores
  作者：Wan-Lei Yu、Hao-Wen Jiang、Lei Yan、Zhi-Tao Feng、Yong-Chun Luo、Peng-Fei Xu

  DOI：10.1007/s11426-020-9852-8

  日期：2021.2

  A photocatalytic tandem cyclization of o-alkenylbenzaldehydes using pyridinium salts as the amination reagent is described. A variety of valuable seven-membered nitrogenous heterocyclic skeletons are prepared in modest to excellent yields in concise one-step. This transformation features mild reaction conditions and exceptional functional group tolerance. In addition, combining control experiments and density functional theory (DFT) calculations on the mechanism can explain the reaction selectivity.

  描述了一种使用吡啶盐作为胺化试剂的光催化串联环化反应，该反应适用于o-烯基苯甲醛。通过简单的一步反应，可以在适中到优秀的产率下制备多种有价值的七元氮杂环骨架。该转化具有温和的反应条件和出色的功能团耐受性。此外，结合对照实验和密度泛函理论(DFT)计算，可以解释反应的选择性。
• Rh(I)-catalyzed CO gas-free carbonylative cyclization of organic halides with tethered nucleophiles using aldehydes as a substitute for carbon monoxide
  作者：Tsumoru Morimoto、Masahiko Fujioka、Koji Fuji、Ken Tsutsumi、Kiyomi Kakiuchi

  DOI：10.1016/j.jorganchem.2006.08.038

  日期：2007.1

  The CO gas-free carbonylative cyclization of organic halides, with tethered nitrogen, oxygen, and carbon nucleophiles, with aldehydes as a substitute for carbon monoxide can be achieved in the presence of a catalytic amount of a rhodium complex. The reaction involves the decarbonylation of the aldehyde by the rhodium catalyst, and the successive carbonylation of an organic halide utilizing the rhodium carbonyl that is formed in situ. Aldehydes having electron-withdrawing groups showed a higher ability to donate the carbonyl moiety. (c) 2006 Elsevier B.V. All rights reserved.