4-phenyl-1-tosyl-1,2,3,6-tetrahydropyridine | 99099-57-7

• 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-phenyl-1-tosyl-1,2,3,6-tetrahydropyridine
• 英文别名: 4-Phenyl-1,2,3,6-tetrahydro-1-(para-tolylsulfonyl)-pyridine；1-(4-methylphenyl)sulfonyl-4-phenyl-3,6-dihydro-2H-pyridine
• CAS: 99099-57-7
• 化学式: C₁₈H₁₉NO₂S
• 分子量: 313.42
• InChiKey: GUGOGDZQXGYQFL-UHFFFAOYSA-N

物化性质

• 熔点：
  203 °C
• 沸点：
  472.5±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 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：
  3

反应信息

• 作为反应物：
  描述：

  4-phenyl-1-tosyl-1,2,3,6-tetrahydropyridine 在 palladium on activated charcoal ammonium cerium(IV) nitrate 、 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (3S,4R)-1-(4-methylphenyl)sulfonyl-4-phenylpiperidine-3,4-diol
  参考文献：
  名称：

  Aminohydroxylation and dihydroxylation of 4-aryl-1,2,5,6-tetrahydropyridines

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2006.05.174
• 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-phenyl-1-tosyl-1,2,3,6-tetrahydropyridine
  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

• Synthese und analgetische Wirkung einiger 4-Phenyl-piperidin-(4)-alkylsulfone. 2. Mitteilung
  作者：J. Büchi、M. Prost、E. Eichenberger、R. Lieberherr

  DOI：10.1002/hlca.19530360409

  日期：——

  Es wird die Herstellung von 1-Methyl-4-(m-methoxyphenyl)-, 1-Methyl-4-(m-acetoxyphenyl)- und 1-Methyl-4-(m-oxyphenyl)-piperidin-(4)-äthylsulfon-hydrohalogeniden beschrieben. Die m-Acetoxy-Verbindung zeigt bei verminderter Toxizität dieselbe analgetische Wirkung wie Dolantin.

  可以将1-甲基-4-（间甲氧基苯基）-，1-甲基-4-（间乙酰氧基苯基）-和1-甲基-4-（间氧基苯基）-哌啶-（4）-乙硫基酮-氢卤代亚苄基苯胺。死于乙型肝炎，死于毒物，死于柴油。
• 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。
• FeCl3-catalyzed cyclization of α-sulfonamido-allenes with aldehydes—the substituent effect
  作者：Jiajia Cheng、Xinjun Tang、Yihua Yu、Shengming Ma

  DOI：10.1039/c2cc36941a

  日期：——

  FeCl3-catalyzed aza-Prins-cyclization reaction of α-sulfonamido-allenes with aldehydes afforded 1,2,3,6-tetrahydropyridine or 2,5-dihydro-1H-pyrrole derivatives efficiently and highly selectively. The different regioselectivity is probably caused by the stabilizing effect of the phenyl group on the positively charged allylic intermediate.

  在 FeCl3 催化下，δ-磺酰胺基亚庚烯与醛的氮杂-普林环化反应高效且高选择性地生成了 1,2,3,6- 四氢吡啶或 2,5- 二氢-1H-吡咯衍生物。不同的区域选择性可能是由于苯基对带正电荷的烯丙基中间体的稳定作用造成的。
• Selectfluor-promoted fluorination of piperidinyl olefins
  作者：Meng-Yang Chang、Nien-Chia Lee、Ming-Fang Lee、Yu-Ping Huang、Chung-Han Lin

  DOI：10.1016/j.tetlet.2010.08.090

  日期：2010.11

  4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate (Selectfluor) is reported. Two transformations from endo-olefin 1 to allylic fluoride 3 and from exo-olefin 2 to fluorohydrin 6 proceed via allylic fluorination and fluorohydroxylation in moderate yields. It presents two novel reactions promoted by Selectfluor and broadens the scope of application.

  通过哌啶子基外表皮的处理，简单而直接地合成1-取代的4-芳基-5-氟-1,2,3,6-四氢吡啶（3）或1-取代的4-二芳基甲酰基-4-氟哌啶（6）-或内烯烃与1-氯甲基-4-氟-1,4-二氮鎓双环[2.2.2]辛烷双（四氟硼酸盐（的Selectfluor）报道从两次转变。内切α-烯烃1至烯丙基氟化物3和从外烯烃2至氟代醇6通过烯丙基氟化和氟羟基化进行中等收率。它展示了Selectfluor促进的两个新颖反应，并扩大了应用范围。
• Decarboxylative Ring Contractions and Olefin Insertions of Vinyl Oxazinanones
  作者：Chao Wang、Jon A. Tunge

  DOI：10.1021/ol0610744

  日期：2006.7.1

  6-Vinyl oxazinanones undergo catalytic, diastereoselective, decarboxylative ring contraction to form vinyl azetidines in good yield. Performing the decarboxylation in the presence of Michael acceptors results in decarboxylative olefin insertion to provide diastereoenriched substituted vinyl piperidines.