cis-4-chloro-2-heptyl-1-tosylpiperidine

• 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: cis-4-chloro-2-heptyl-1-tosylpiperidine
• 英文别名: cis-N-tosyl-4-chloro-2-heptylpiperidine；(2R,4R)-4-chloro-2-heptyl-1-(4-methylphenyl)sulfonylpiperidine
• 化学式: C₁₉H₃₀ClNO₂S
• 分子量: 371.972
• InChiKey: UKKVISVMXLEGHC-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  正辛醛 、 N-(3-丁烯-1-基)-4-甲基苯磺酰胺 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 cis-4-chloro-2-heptyl-1-tosylpiperidine 、 trans-4-chloro-2-heptyl-1-tosylpiperidine
  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

• 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.