N-(3,3-bis(4-fluorobenzyl)pent-4-enyl)-4-methylbenzenesulfonamide | 1252671-25-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(3,3-bis(4-fluorobenzyl)pent-4-enyl)-4-methylbenzenesulfonamide
• 英文别名: N-[3,3-bis[(4-fluorophenyl)methyl]pent-4-enyl]-4-methylbenzenesulfonamide
• CAS: 1252671-25-2
• 化学式: C₂₆H₂₇F₂NO₂S
• 分子量: 455.569
• InChiKey: ULMGFQJSJJTCOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3,3-bis(4-fluorobenzyl)pent-4-enyl)-4-methylbenzenesulfonamide 在 copper(II) 2-ethylhexanoate 、 potassium carbonate 作用下， 以 三氟甲苯 为溶剂， 反应 24.0h， 生成 7-fluoro-3a-[(4-fluorophenyl)methyl]-1-(4-methylphenyl)sulfonyl-3,4,9,9a-tetrahydro-2H-benzo[f]indole
  参考文献：
  名称：

  Diastereo- and Enantioselective Copper-Catalyzed Intramolecular Carboamination of Alkenes for the Synthesis of Hexahydro-1H-benz[f]indoles

  摘要：

  A new method for the enantioselective synthesis of hexahydro-1H-benz[f]indoles is described. This copper-catalyzed enantioselective intramolecular alkene carboamination process can install vicinal tertiary and quaternary carbon stereocenters with high levels of diastereo- and enantioselectivity. The C-C bond-forming component of the reaction constitutes a C-H functionalization and no electronic activation of the aryl ring that undergoes addition is required. A known 5-HT1A receptor antagonist was synthesized efficiently using this method.

  DOI：

  10.1021/ol102233g
• 作为产物：
  描述：

  、 对甲苯磺酰胺 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 N-(3,3-bis(4-fluorobenzyl)pent-4-enyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Diastereo- and Enantioselective Copper-Catalyzed Intramolecular Carboamination of Alkenes for the Synthesis of Hexahydro-1H-benz[f]indoles

  摘要：

  A new method for the enantioselective synthesis of hexahydro-1H-benz[f]indoles is described. This copper-catalyzed enantioselective intramolecular alkene carboamination process can install vicinal tertiary and quaternary carbon stereocenters with high levels of diastereo- and enantioselectivity. The C-C bond-forming component of the reaction constitutes a C-H functionalization and no electronic activation of the aryl ring that undergoes addition is required. A known 5-HT1A receptor antagonist was synthesized efficiently using this method.

  DOI：

  10.1021/ol102233g

文献信息

• Enantioselective, Aerobic Copper-Catalyzed Intramolecular Carboamination and Carboetherification of Unactivated Alkenes
  作者：Tomasz Wdowik、Samuel L. Galster、Raul L. L. Carmo、Sherry R. Chemler

  DOI：10.1021/acscatal.0c02607

  日期：2020.8.7

  Reduction of waste is an important goal of modern organic synthesis. We report herein oxidase reactivity for enantioselective intramolecular copper-catalyzed alkene carboamination and carboetherification reactions where previously used stoichiometric MnO2 has been replaced with oxygen. This substitution was risky as the reaction mechanism is thought to involve C–C bond formation via addition of alkyl

  减少废物是现代有机合成的一个重要目标。我们在此报告了对映选择性分子内铜催化的烯烃碳胺化和碳醚化反应的氧化酶反应性，其中先前使用的化学计量的 MnO 2已被氧取代。这种取代是有风险的，因为反应机制被认为涉及通过将烷基碳自由基加成到芳烃上形成 C-C 键。这些中间体也容易通过 O 2加成形成 C-O 键。在有氧条件下对绝对立体化学的控制也不确定。氧化环化效率似乎随着芳烃中自由基加成的容易程度而变化。
• Diastereo- and Enantioselective Copper-Catalyzed Intramolecular Carboamination of Alkenes for the Synthesis of Hexahydro-1<i>H</i>-benz[<i>f</i>]indoles
  作者：Lei Miao、Imranul Haque、Maria R. Manzoni、Weng Siong Tham、Sherry R. Chemler

  DOI：10.1021/ol102233g

  日期：2010.11.5

  A new method for the enantioselective synthesis of hexahydro-1H-benz[f]indoles is described. This copper-catalyzed enantioselective intramolecular alkene carboamination process can install vicinal tertiary and quaternary carbon stereocenters with high levels of diastereo- and enantioselectivity. The C-C bond-forming component of the reaction constitutes a C-H functionalization and no electronic activation of the aryl ring that undergoes addition is required. A known 5-HT1A receptor antagonist was synthesized efficiently using this method.