trans-2-benzyl-4-chloro-1-tosylpiperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: trans-2-benzyl-4-chloro-1-tosylpiperidine
• 英文别名: trans-N-tosyl-2-benzyl-4-chloropiperidine；(2S,4R)-2-benzyl-4-chloro-1-(4-methylphenyl)sulfonylpiperidine
• 化学式: C₁₉H₂₂ClNO₂S
• 分子量: 363.908
• InChiKey: VCXDONPFJSSBIV-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  氧化苯乙烯 、 N-(3-丁烯-1-基)-4-甲基苯磺酰胺 在 bismuth(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到trans-2-benzyl-4-chloro-1-tosylpiperidine
  参考文献：
  名称：

  BiCl 3促进aza-Prins型环化：快速有效地合成2,4-二取代的哌啶

  摘要：

  将几种N-保护的高烯丙基胺和环氧化物进行氮杂-Prins环化。实现了快速有效的BiCl 3促进的反式-2,4-二取代哌啶衍生物的立体选择性合成。

  DOI：

  10.1016/j.tetlet.2007.12.072

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。
• 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.
• 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.
• Application of biphasic reaction procedure using ferric chloride dissolved in an imidazolium salt and benzotrifluoride (FeIm-BTF procedure) to aza-Prins cyclization reaction
  作者：Eietsu Hasegawa、Nohara Hiroi、Chika Osawa、Eiji Tayama、Hajime Iwamoto

  DOI：10.1016/j.tetlet.2010.10.018

  日期：2010.12

  Aza-Prins cyclization reaction of N-tosyl-3-butenylamine with aliphatic and aromatic aldehydes was performed using a combination of FeCl3 and 1-butyl-3-methylimidazolium hexafluorophosphate (BmimPF(6)) or 1-butyl-3-methylimidazolium tetrachloroferrate (BmimFeCl(4)) in benzotrifluoride (BTF). The desired N-tosyl-4-chloro-2-substituted piperidines were obtained from aliphatic aldehydes in comparable yields to those for the previously reported reactions in which FeCl3 was used in CH2Cl2. On the other hand, significant progress for the piperidine synthesis from aromatic aldehydes has been achieved, particularly when BmimFeCl(4) was used with FeCl3 in BTF. (C) 2010 Elsevier Ltd. All rights reserved.
• BiCl3 promoted aza-Prins type cyclization: a rapid and efficient synthesis of 2,4-disubstituted piperidines
  作者：M.S.R. Murty、Kesur R. Ram、J.S. Yadav

  DOI：10.1016/j.tetlet.2007.12.072

  日期：2008.2

  Several N-protected homoallyl amines and epoxides were subjected to an aza-Prins cyclization. A rapid and efficient BiCl3 promoted stereoselective synthesis of trans-2,4-disubstituted piperidine derivatives was achieved.

  将几种N-保护的高烯丙基胺和环氧化物进行氮杂-Prins环化。实现了快速有效的BiCl 3促进的反式-2,4-二取代哌啶衍生物的立体选择性合成。