4-(4-chlorophenyl)-1-(4-methylphenyl)sulfonyl-3,6-dihydro-2H-pyridine | 877614-66-9

• 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-chlorophenyl)-1-(4-methylphenyl)sulfonyl-3,6-dihydro-2H-pyridine
• CAS: 877614-66-9
• 化学式: C₁₈H₁₈ClNO₂S
• 分子量: 347.865
• InChiKey: UBIUWKKDAYGYPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-1-(4-methylphenyl)sulfonyl-3,6-dihydro-2H-pyridine 在 palladium on activated charcoal sodium azide 、 ammonium cerium(IV) nitrate 、 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 11.0h， 生成 (3S,4R)-3-amino-1-(4-methylphenyl)sulfonyl-4-phenylpiperidin-4-ol
  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-(4-chlorophenyl)-1-(4-methylphenyl)sulfonyl-3,6-dihydro-2H-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

• New synthesis of 3-arylpyrrolines
  作者：Meng-Yang Chang、Chun-Li Pai、Yung-Hua Kung

  DOI：10.1016/j.tetlet.2005.12.008

  日期：2006.2

  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.
• 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.