2-benzyl-4-bromo-1,2,5,6-tetrahydro-1-tosylpyridine

• 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: 2-benzyl-4-bromo-1,2,5,6-tetrahydro-1-tosylpyridine
• 英文别名: 6-benzyl-4-bromo-1-(4-methylphenyl)sulfonyl-3,6-dihydro-2H-pyridine
• 化学式: C₁₉H₂₀BrNO₂S
• 分子量: 406.343
• InChiKey: BEYUGVHCADEWKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2-羟基丙基)-4-甲基苯磺酰胺 在 ferric(III) bromide 、 pyridine-SO3 complex 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 2-benzyl-4-bromo-1,2,5,6-tetrahydro-1-tosylpyridine
  参考文献：
  名称：

  Iron(III)-Promoted Aza-Prins-Cyclization:  Direct Synthesis of Six-Membered Azacycles

  摘要：

  A new iron(III) halide-promoted aza-Prins cyclization between gamma,delta-unsaturated tosylamines and aldehydes provides six-membered azacycles in good to excellent yields. The process is based on the consecutive generation of gamma-unsaturated-iminium ion and further nucleophilic attack by the unsaturated carbon-carbon bond. Homoallyl tosylamine leads to trans-2-alkyl-4-halo-1-tosylpiperidine as the major isomer. In addition, the alkyne aza-Prins cyclization between homopropargyl tosylamine and aldehydes gives 2-alkyl-4-halo-1-tosyl-1,2,5,6-tetrahydropyridines as the only cyclic products.

  DOI：

  10.1021/ol061448t

文献信息

• A New Catalytic Prins Cyclization Leading to Oxa- and Azacycles
  作者：Pedro O. Miranda、Rubén M. Carballo、Víctor S. Martín、Juan I. Padrón

  DOI：10.1021/ol802593u

  日期：2009.1.15

  A new Prins cyclization process that builds up one carbon−carbon bond, one heteroatom-carbon bond, and one halogen-carbon bond, (in an oxa- and azacycle) relies on an iron catalyst system formed from Fe(acac)3 and trimethylsilyl halide. The method displays a broad substrate scope and is economical, environmentally friendly, and experimentally simple. This catalytic method permits the construction of

  新的Prins环化过程建立一个碳-碳键，一个杂原子-碳键和一个卤素-碳键（在氧杂和氮杂环中）依赖于由Fe（acac）3和三甲基甲硅烷基形成的铁催化剂体系卤化物。该方法显示出广泛的底物范围，并且经济，环境友好并且实验简单。该催化方法允许通过铁（III）源，相应的三甲基甲硅烷基卤化物和溶剂的适当组合以高收率构造氯，溴和碘杂环。
• Antiproliferative activity of 2-alkyl-4-halopiperidines and 2-alkyl-4-halo-1,2,5,6-tetrahydropyridines in solid tumor cell lines
  作者：Leticia G. León、Rubén M. Carballo、María C. Vega-Hernández、Víctor S. Martín、Juan I. Padrón、José M. Padrón

  DOI：10.1016/j.bmcl.2007.03.010

  日期：2007.5

  A series of trans-2-alkyl-4-halopiperidines and 2-alkyl-4-halo-1,2,5,6-tetrahydropyridines were prepared by means of an iron(III) catalyzed process. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780 (ovarian cancer), SW1573 (non-small cell lung cancer), and WiDr (colon cancer). The results on the biological activity revealed that, in general, the 2-alkyl-4-halo-1,2,5,6-tetrahydropyridine analogs are more potent than the trans-2-alkyl-4-halopiperidine derivatives. A remarkable selectivity of the aza compound 5f for the resistant cell line WiDr was observed. Cell cycle studies revealed a G(2)/M phase arrest for 5f. (c) 2007 Elsevier Ltd. All rights reserved.
• Iron(III)-Promoted Aza-Prins-Cyclization:  Direct Synthesis of Six-Membered Azacycles
  作者：Rubén M. Carballo、Miguel A. Ramírez、Matías L. Rodríguez、Víctor S. Martín、Juan I. Padrón

  DOI：10.1021/ol061448t

  日期：2006.8.1

  A new iron(III) halide-promoted aza-Prins cyclization between gamma,delta-unsaturated tosylamines and aldehydes provides six-membered azacycles in good to excellent yields. The process is based on the consecutive generation of gamma-unsaturated-iminium ion and further nucleophilic attack by the unsaturated carbon-carbon bond. Homoallyl tosylamine leads to trans-2-alkyl-4-halo-1-tosylpiperidine as the major isomer. In addition, the alkyne aza-Prins cyclization between homopropargyl tosylamine and aldehydes gives 2-alkyl-4-halo-1-tosyl-1,2,5,6-tetrahydropyridines as the only cyclic products.