6-(10-bromodecyl)-4-chloro-1-tosyl-1,2,3,6-tetrahydropyridine | 910050-88-3

• 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: 6-(10-bromodecyl)-4-chloro-1-tosyl-1,2,3,6-tetrahydropyridine
• 英文别名: 6-(10-bromodecyl)-4-chloro-1-(4-methylphenyl)sulfonyl-3,6-dihydro-2H-pyridine
• CAS: 910050-88-3
• 化学式: C₂₂H₃₃BrClNO₂S
• 分子量: 490.933
• InChiKey: VTJXKWVNFNNFFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(10-bromodecyl)-4-chloro-1-tosyl-1,2,3,6-tetrahydropyridine 在 三氯化铁 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.17h， 生成 4-chloro-2-(10-(4-chloro-1,2,5,6-tetrahydro-1-tosylpyridin-2-yl)decyl)-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
• 作为产物：
  描述：

  N-(2-羟基丙基)-4-甲基苯磺酰胺 在 pyridine-SO3 complex 、 三氯化铁 、 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 6-(10-bromodecyl)-4-chloro-1-tosyl-1,2,3,6-tetrahydropyridine
  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.