5-fluoro-1-tosyl-3-vinyl-1H-indole | 858101-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-fluoro-1-tosyl-3-vinyl-1H-indole
• 英文别名: 5-fluoro-1-tosyl-3-vinylindole；3-Ethenyl-5-fluoro-1-(4-methylphenyl)sulfonylindole；3-ethenyl-5-fluoro-1-(4-methylphenyl)sulfonylindole
• CAS: 858101-83-4
• 化学式: C₁₇H₁₄FNO₂S
• 分子量: 315.368
• InChiKey: ZUMQJVBKRPZUCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-fluoro-1-tosyl-3-vinyl-1H-indole 、 3,4-dihydro-isoquinoline 2-oxide 以 甲苯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis and hSERT activity of homotryptamine analogs. Part 6: [3+2] dipolar cycloaddition of 3-vinylindoles

  摘要：

  Substituted 1-tosyl-3-vinylindoles undergo [3+2] dipolar cycloaddition with cyclic nitrones to afford substituted isoxazoles in good yield and high diastereoselectivity. The cycloadducts were readily converted in 4 steps into ring constrained homotryptamine analogs. These analogs exhibited excellent binding affinity for the human serotonin transporter (hSERT). Indoles bearing a 5-cyano group and a pendent ethyl(tetrahydroisoquinoline) moiety at the 3-position displayed the best potency for hSERT and high selectivity versus hDAT and hNET. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.043
• 作为产物：
  描述：

  甲基三苯基溴化膦 、 5-fluoro-1-(p-tolylsulfonyl)indole-3-carboxaldehyde 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以87%的产率得到5-fluoro-1-tosyl-3-vinyl-1H-indole
  参考文献：
  名称：

  Catalytic Asymmetric Diazoacetate Cyclopropanation of 1-Tosyl-3-vinylindoles. A Route to Conformationally Restricted Homotryptamines

  摘要：

  Substituted 1-tosyl-3-vinylindoles undergo catalytic asymmetric cyclopropanation with ethyl- and tert-butyldiazoacetate to afford N-protected trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters in good yield and high enantiomeric excess (81-88% ee). The resulting cycloadducts are demonstrated to be useful intermediates for the synthesis of conformationally restricted, homotryptamine-like analogues such as BMS-505130.

  DOI：

  10.1021/ol050790n

文献信息

• Catalytic Asymmetric Diazoacetate Cyclopropanation of 1-Tosyl-3-vinylindoles. A Route to Conformationally Restricted Homotryptamines
  作者：Lawrence R. Marcin、Derek J. Denhart、Ronald J. Mattson

  DOI：10.1021/ol050790n

  日期：2005.6.1

  Substituted 1-tosyl-3-vinylindoles undergo catalytic asymmetric cyclopropanation with ethyl- and tert-butyldiazoacetate to afford N-protected trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters in good yield and high enantiomeric excess (81-88% ee). The resulting cycloadducts are demonstrated to be useful intermediates for the synthesis of conformationally restricted, homotryptamine-like analogues such as BMS-505130.
• Synthesis and hSERT activity of homotryptamine analogs. Part 6: [3+2] dipolar cycloaddition of 3-vinylindoles
  作者：Lawrence R. Marcin、Ronald J. Mattson、Qi Gao、Dedong Wu、Thaddeus F. Molski、Gail K. Mattson、Nicholas J. Lodge

  DOI：10.1016/j.bmcl.2009.12.043

  日期：2010.2

  Substituted 1-tosyl-3-vinylindoles undergo [3+2] dipolar cycloaddition with cyclic nitrones to afford substituted isoxazoles in good yield and high diastereoselectivity. The cycloadducts were readily converted in 4 steps into ring constrained homotryptamine analogs. These analogs exhibited excellent binding affinity for the human serotonin transporter (hSERT). Indoles bearing a 5-cyano group and a pendent ethyl(tetrahydroisoquinoline) moiety at the 3-position displayed the best potency for hSERT and high selectivity versus hDAT and hNET. (C) 2009 Elsevier Ltd. All rights reserved.