1-phenylsulfonyl-3-(4-fluorophenyl)indole | 1340592-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-phenylsulfonyl-3-(4-fluorophenyl)indole
• 英文别名: 3-(4-fluorophenyl)-1-(phenylsulfonyl)indole
• CAS: 1340592-97-3
• 化学式: C₂₀H₁₄FNO₂S
• 分子量: 351.401
• InChiKey: WXBLODKESKXZCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-phenylsulfonyl-3-(4-fluorophenyl)indole 在 甲醇 、 氯化铵 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以89%的产率得到3-(4-氟-苯基)-1H-吲哚
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of indole-based sigma receptor ligands

  摘要：

  A series of novel indole-based analogs were prepared and their affinities for sigma receptors were determined using in vitro radioligand binding assays. The results of this study identified several compounds with nanomolar sigma-2 affinity and significant selectivity over sigma-1 receptors. In particular, 2-(4-(3-(4-fluorophenyl)indol-1-yl)butyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (9f) was found to display high affinity at sigma-2 receptors with good selectivity (sigma-1/sigma-2 = 395). The pharmacological binding profile for this compound was established with other relevant non-sigma sites. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.031
• 作为产物：
  描述：

  4-氟苯硼酸 、 3-溴-(1-苯磺酰)吲哚 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 反应 16.0h， 以91%的产率得到1-phenylsulfonyl-3-(4-fluorophenyl)indole
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of indole-based sigma receptor ligands

  摘要：

  A series of novel indole-based analogs were prepared and their affinities for sigma receptors were determined using in vitro radioligand binding assays. The results of this study identified several compounds with nanomolar sigma-2 affinity and significant selectivity over sigma-1 receptors. In particular, 2-(4-(3-(4-fluorophenyl)indol-1-yl)butyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (9f) was found to display high affinity at sigma-2 receptors with good selectivity (sigma-1/sigma-2 = 395). The pharmacological binding profile for this compound was established with other relevant non-sigma sites. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.031

文献信息

• Catalyst-Controlled Regioselectivity in Pd-Catalyzed Aerobic Oxidative Arylation of Indoles
  作者：Dian Wang、Chase A. Salazar、Shannon S. Stahl

  DOI：10.1021/acs.organomet.1c00139

  日期：2021.7.26

  synthetic transformation; however, the regioselectivity is often substrate-controlled. Here, we report catalyst-controlled regioselectivity in the Pd-catalyzed oxidative coupling of N-(phenylsulfonyl)indoles and aryl boronic acids using O2 as the oxidant. Both C2- and C3-arylated indoles are obtained in good yield with >10:1 selectivity. A switch from C2 to C3 regioselectivity is achieved by adding 4,5-diazafluoren-9-one

  Pd催化的杂芳烃的C-H芳基化是一种重要且广泛研究的合成转化；然而，区域选择性通常是受底物控制的。在这里，我们报告了使用 O 2作为氧化剂的 Pd 催化的N- (苯磺酰基)吲哚和芳基硼酸的氧化偶联中催化剂控制的区域选择性。C2-和 C3-芳基化吲哚均以 >10:1 的选择性高产率获得。通过将 4,5-diazafluoren-9-one 或 2,2'-二嘧啶作为辅助配体添加到“无配体”Pd(OTs) 2中，实现了从 C2 到 C3 区域选择性的转换催化剂体系。密度泛函理论计算表明，选择性的转换源于机制的变化，从 C2 选择性氧化-Heck 途径到 C3 选择性 C-H 活化/还原消除途径。