4-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridine | 516477-38-6

• 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: 4-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridine
• 英文别名: 4-(4-fluorophenyl)-1-(4-methylphenyl)sulfonyl-3,6-dihydro-2H-pyridine
• CAS: 516477-38-6
• 化学式: C₁₈H₁₈FNO₂S
• 分子量: 331.411
• InChiKey: MXLIEWDCBOOGBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridine 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 3-(4-fluorophenyl)-1-tosyl-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  New synthesis of 3-arylpyrrolines

  摘要：

  We present an easy and straightforward synthesis of 3-arylpyrrolines 4a-g by repeated treatment of 4-aryl-1,2,5,6-tetrahydropyridines 2a-g with in-chloroperoxybenzoic acid (MCPBA) and boron trifluoride etherate (BF3-OEt2). The transformation proceeds via epoxidation, ring contraction, Baeyer-Villiger oxidation and elimination reaction and affords 3-arylpyrrolines 4a-g with 61-70% yield. This facile strategy was also used to synthesize racemic baclofen (6). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.008
• 作为产物：
  描述：

  1-[(4-甲苯)磺酰基]-4-哌啶醇 在 jones reagent 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.5h， 生成 4-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridine
  参考文献：
  名称：

  New synthesis of 3-arylpyrrolines

  摘要：

  We present an easy and straightforward synthesis of 3-arylpyrrolines 4a-g by repeated treatment of 4-aryl-1,2,5,6-tetrahydropyridines 2a-g with in-chloroperoxybenzoic acid (MCPBA) and boron trifluoride etherate (BF3-OEt2). The transformation proceeds via epoxidation, ring contraction, Baeyer-Villiger oxidation and elimination reaction and affords 3-arylpyrrolines 4a-g with 61-70% yield. This facile strategy was also used to synthesize racemic baclofen (6). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.008

文献信息

• Synthesis of cis-3,4-diarylpiperidines and cis-3,4-diaryltetrahydropyrans
  作者：Meng-Yang Chang、Chun-Yu Lin、Ching-Yi Hung

  DOI：10.1016/j.tet.2007.02.055

  日期：2007.4

  following sequence: (1) pinacol-type ring contraction having the combination of m-chloroperoxybenzoic acid and boron trifluoride etherate, (2) Grignard addition with arylmagnesium bromide reagents and followed by boron trifluoride etherate-mediated intramolecular ring-expanded rearrangement, and (3) hydrogenation with hydrogen on 10% palladium-activated carbon. A facile synthesis of 3,4-diarylpyridines

  取代的顺式-3,4-二芳基哌啶和顺式-3,4-二芳基四氢吡喃以适度的总收率合成，起始于4-芳基-1,2,5,6-四氢吡啶和4-芳基-1,2,5,6-通过以下顺序的四氢吡喃：（1）频哪醇型具有的组合环收缩米氯过氧酸和三氟化硼醚，（2）格氏加成与芳基溴化镁试剂和随后三氟化硼醚介导的分子内环扩展重排， （3）在10％钯活化的碳上用氢加氢。还通过碱诱导的芳构化描述了3，4-二芳基吡啶的容易的合成。
• New synthesis of cis-3,4-diaryl-1-tosylpyrrolidines
  作者：Meng-Yang Chang、Chun-Li Pai、Chun-Yu Lin

  DOI：10.1016/j.tetlet.2006.03.141

  日期：2006.5

  Unsymmetrically substituted cis-3,4-diarylpyrrolidines are synthesized in nearly 25% overall yields starting from 4-aryl-1,2,5,6-tetrahydropyridines by iterative reactions using the combination of m-chloroperoxybenzoic acid (MCPBA) and boron trifluoride etherate (BF3 center dot OEt2) followed by Grignard addition, elimination and hydrogenation sequence. (c) 2006 Elsevier Ltd. All rights reserved.
• Aminohydroxylation and dihydroxylation of 4-aryl-1,2,5,6-tetrahydropyridines
  作者：Meng-Yang Chang、Chun-Yu Lin、Tsun-Cheng Wu

  DOI：10.1016/j.tetlet.2006.05.174

  日期：2006.7

  Substituted 3-amino-4-aryl-4-liydi-oxypiperidines and 4-aryl-3.4-dihvdroxypiperidiiies are synthesized in the modest overall yields starting from the regio- and stereoselective trans-aminohydroxylation and dihydroxylation of 4-aryl-1,15.6-tetrahydropyridines via CAN-mediated oxidative addition and hydrogenation. (c) 2006 Elsevier Ltd. All rights reserved.