1-苯磺酰基-3-哌啶酮 | 267666-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯磺酰基-3-哌啶酮
• 英文名称: N-benzenesulfonyl-3-piperidone
• 英文别名: N-phenylsulfonyl-3-piperidone；1-(Benzenesulfonyl)piperidin-3-one
• CAS: 267666-10-4
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: CHNPGJQSBBJGFC-UHFFFAOYSA-N

物化性质

• 熔点：
  77-78℃ (ethyl acetate hexane )

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-苯磺酰基-3-哌啶酮 在 三氯化铝 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 10.5h， 生成 N-(2-benzenesulfonyl-8-methoxy-1,2,3,4-tetrahydrobenzo[4,5]furo[2,3-c]pyridin-6-yl)benzenesulfonamide
  参考文献：
  名称：

  Lewis Acid-Directed Cyclocondensation of Piperidone Enol Ethers with 2-Methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine:  A New Regioselective Synthesis of Oxygenated Carbolines

  摘要：

  Lewis acid-directed cyclocondensations of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine are reported. Benzofurans are obtained with BF3. OEt2 as a promoter, whereas use of excess amounts of TiCl4:Ti(OiPr)(4) leads to tetrahydrocarbolines. The latter reactions provide expedient routes to oxygen-substituted tetrahydrocarbolines and carbolines. As applications of this new methodology, the preparations of 1-[3-(dimethylamino)propyl] amino-7-methoxy- and 1-[3-(dimethylamino)propyl]amino-7,8-dimethoxy-5H-pyrido[4,3-b]indoles are described.

  DOI：

  10.1021/jo9916176
• 作为产物：
  描述：

  3-羟基哌啶 在 三乙胺 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 1-苯磺酰基-3-哌啶酮
  参考文献：
  名称：

  Synthesis of 1,2,4-trisubstituted-1,2,5,6-tetrahydropyridines

  摘要：

  A novel method for the synthesis of 1,2,4-trisubstituted- or 1,2,3,4-tetrasubstituted-1,2,5,6-tetrahydropyridine is presented. The process was carried out by the bromomethoxylation of 4-substituted-1,2,5,6-tetrahydropyridines 1 with N-bromosuccinimide (NBS) in methanol, dehydrobromination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF(3)-OEt(2))-catalyzed cross coupling of the corresponding enamine with trimethylsilyl-based nucleophiles. Homokainoid analogs were also synthesized via the protocol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.131

文献信息

• Rh₂(II)-Catalyzed Selective Aminomethylene Migration from Styryl Azides
  作者：Chen Kong、Navendu Jana、Tom G. Driver

  DOI：10.1021/ol400137q

  日期：2013.2.15

  Rh2(II)-Carboxylate complexes were discovered to promote the selective migration of aminomethylenes in β,β-disubstituted styryl azides to form 2,3-disubstituted indoles. Mechanistic data are also presented that suggest that the migration occurs stepwise before diffusion of the iminium ion.

  发现Rh 2 (II)-羧酸盐配合物可促进氨基亚甲基在 β,β-二取代苯乙烯基叠氮化物中的选择性迁移形成 2,3-二取代吲哚。还提供了表明迁移在亚胺离子扩散之前逐步发生的机械数据。
• Synthesis of rodocaine
  作者：Meng-Yang Chang、Hang-Yi Tai、Yeh-Long Chen

  DOI：10.1016/j.tet.2011.08.025

  日期：2011.10

  A new method for synthesis of rodocaine (1) is presented. Two key steps were carried out by the N-bromosuccinimide (NBS)-mediated intermolecular addition of known enamine 5 with allyltrimethyl silane in presence of boron trifluoride etherate (BF3/OEt2) and the intramolecular ring-closing metathesis of triene 3. The Diels-Alder cycloaddition of triene 3 with different ethyl propiolates was also studied. (C) 2011 Elsevier Ltd. All rights reserved.
• Skeletal Diversification via Heteroatom Linkage Control: Preparation of Bicyclic and Spirocyclic Scaffolds from N-Substituted Homopropargyl Alcohols
  作者：Thomas O. Painter、Jonathon R. Bunn、Frank J. Schoenen、Justin T. Douglas、Victor W. Day、Conrad Santini

  DOI：10.1021/jo400077m

  日期：2013.4.19

  The discovery and application of a new branching pathway synthesis strategy that rapidly produces skeletally diverse scaffolds is described. Two different scaffold types, one a bicyclic iodo-vinylidene tertiary amine/tertiary alcohol and the other, a spirocyclic 3-furanone, are each obtained using a two-step sequence featuring a common first step. Both scaffold types lead to intermediates that can be orthogonally diversified using the same final components. One of the scaffold types was obtained in sufficiently high yield that it was immediately used to produce a 97 compound library.
• Synthesis of Furo[2,3-b]pyridine
  作者：Meng-Yang Chang、Hang-Yi Tai

  DOI：10.3987/com-11-12305

  日期：——

  Two synthetic routes toward furo[2,3-b]pyridine (1) starting with the known beta,gamma-unsaturated ester (3) are described.
• Synthesis of 1,2,4-trisubstituted-1,2,5,6-tetrahydropyridines
  作者：Meng-Yang Chang、Ming-Fang Lee、Nien-Chia Lee、Yu-Ping Huang、Chung-Han Lin

  DOI：10.1016/j.tetlet.2010.11.131

  日期：2011.2

  A novel method for the synthesis of 1,2,4-trisubstituted- or 1,2,3,4-tetrasubstituted-1,2,5,6-tetrahydropyridine is presented. The process was carried out by the bromomethoxylation of 4-substituted-1,2,5,6-tetrahydropyridines 1 with N-bromosuccinimide (NBS) in methanol, dehydrobromination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF(3)-OEt(2))-catalyzed cross coupling of the corresponding enamine with trimethylsilyl-based nucleophiles. Homokainoid analogs were also synthesized via the protocol. (C) 2010 Elsevier Ltd. All rights reserved.