N-(3-(2-methoxybenzyl)pent-4-enyl)methanesulfonamide | 1252671-34-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(3-(2-methoxybenzyl)pent-4-enyl)methanesulfonamide
• 英文别名: N-[3-[(2-methoxyphenyl)methyl]pent-4-enyl]methanesulfonamide
• CAS: 1252671-34-3
• 化学式: C₁₄H₂₁NO₃S
• 分子量: 283.392
• InChiKey: XVFNIGVIKRYIOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-(2-methoxybenzyl)pent-4-enyl)methanesulfonamide 在 manganese(IV) oxide 、 4,5-dihydro-2-(2-(4,5-dihydrooxazol-2-yl)propan-2-yl)oxazole 、 copper(II) bis(trifluoromethanesulfonate) 、 potassium carbonate 作用下， 以 三氟甲苯 为溶剂， 生成 (+/-)-cis-5-methoxy-1-(methylsulfonyl)-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]indole 、 (+/-)-trans-5-methoxy-1-(methylsulfonyl)-2,3,3a,4,9,9a-hexahydro-1H-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：

  甲基磺酰胺 、 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以2.21 g的产率得到N-(3-(2-methoxybenzyl)pent-4-enyl)methanesulfonamide
  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