3-(3-methanesulfonylphenyl)piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(3-methanesulfonylphenyl)piperidine
• 英文别名: 3-(3-(Methylsulfonyl)phenyl)piperidine；3-(3-methylsulfonylphenyl)piperidine
• 化学式: C₁₂H₁₇NO₂S
• 分子量: 239.338
• InChiKey: KMVLMAUQHRUFDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

3-(3-(甲基磺酰基)苯基)哌啶是PNU-96391的人类已知代谢物。

3-(3-(Methylsulfonyl)phenyl)piperidine is a known human metabolite of PNU-96391.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  3-(3-methanesulfonylphenyl)piperidine 以>94% ee;72的产率得到PNU-100014
  参考文献：
  名称：

  Tetrahedron Lett. 1994, 48, 9063-9066

  摘要：

  DOI：
• 作为产物：
  描述：

  二乙基(3-吡啶基)-硼烷 在 四(三苯基膦)钯 、 platinum on carbon 、 四丁基溴化铵 、 氢气 、 sodium hydroxide 作用下， 以 四氢呋喃 、 磷酸 、 水 为溶剂， 4.0~98.0 ℃ 、413.7 kPa 条件下， 反应 18.0h， 生成 3-(3-methanesulfonylphenyl)piperidine
  参考文献：
  名称：

  The Synthesis of OSU 6162:  Efficient, Large-Scale Implementation of a Suzuki Coupling

  摘要：

  The synthesis of the chiral, nonracemic 3-aryl piperidine, OSU 6162 ((1) under bar), a potential CNS agent from Pharmacia Corporation, is presented. The key construction in the described synthesis is a palladium-catalyzed aryl cross-coupling reaction between bromosulfone ((4) under bar) and pyridyl borane ((14) under bar). Initially developed conditions for this Suzuki reaction, conducted in tetrahydrofuran/aqueous hydroxide, delivered free base ((6) under bar) or hydrochloride salt ((15a) under bar) in reproducible 80% yield. However, by changing the solvent to toluene and the base to carbonate, significant decreases in catalyst requirement were realized, and the methane sulfonate salt ((15b) under bar) of the coupled product could be obtained in reproducible 92-94% yield on 200-kg input. The success of the Suzuki reaction was critically dependent on a bulk source of the pyridyl borane coupling partner. Cryogenic conditions were developed for its generation via lithium-halogen exchange to generate thermally labile 3-lithiopyridine followed by transmetalation with diethylmethoxy borane. This highly exothermic series of transformations yielded crystalline diethyl-3-pyridyl borane in reproducible 75-80% yield on scales ranging up to 200-kg input. Selective reduction of the biaryl, classical resolution and introduction of the propyl group via the Gribble reductive amination procedure completed the synthesis of OSU 6162 free base. This route was employed to deliver over 35 kg of clinical-quality bulk drug in short order.

  DOI：

  10.1021/op025620u

文献信息

• [EN] SUBSTITUTED CARBAMATE COMPOUNDS AND THEIR USE AS TRANSIENT RECEPTOR POTENTIAL (TRP) CHANNEL ANTAGONISTS<br/>[FR] COMPOSÉS CARBAMATE SUBSTITUÉS ET LEUR UTILISATION EN TANT QU'ANTAGONISTES DU CANAL POTENTIEL RÉCEPTEUR TRANSITOIRE (TRP)
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014060341A1

  公开（公告）日：2014-04-24

  The invention is concerned with the compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein Y, R1 and R3 are defined in the detailed description and claims. In addition, the present invention relates to methods of manufacturing and using the compounds of formula (I) as well as pharmaceutical compositions containing such compounds. The compounds of formula (I) are antagonists of the TRPA1 channel and may be useful in treating inflammatory diseases and disorders associated with that channel.

  该发明涉及式(I)的化合物及其药学上可接受的盐，其中Y、R1和R3在详细描述和权利要求中有定义。此外，本发明涉及制备和使用式(I)的化合物的方法，以及含有这些化合物的药物组合物。式(I)的化合物是TRPA1通道的拮抗剂，可能对治疗与该通道相关的炎症性疾病和紊乱有用。
• SUBSTITUTED CARBAMATE COMPOUNDS
  申请人：HOFFMANN-LA ROCHE INC

  公开号：US20150218141A1

  公开（公告）日：2015-08-06

  The invention is concerned with the compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein Y, R1 and R3 are defined in the detailed description and claims. In addition, the present invention relates to methods of manufacturing and using the compounds of formula (I) as well as pharmaceutical compositions containing such compounds. The compounds of formula (I) are antagonists of the TRPA1 channel and may be useful in treating inflammatory diseases and disorders associated with that channel.

  本发明涉及式(I)的化合物及其药学上可接受的盐，其中Y、R1和R3在详细说明和权利要求中有定义。此外，本发明还涉及制造和使用式(I)化合物的方法，以及含有这些化合物的制药组合物。式(I)化合物是TRPA1通道的拮抗剂，可能有助于治疗与该通道相关的炎症性疾病和障碍。
• PROCESSES FOR PRODUCING RACEMIC PIPERIDINE DERIVATIVE AND FOR PRODUCING OPTICALLY ACTIVE PIPERIDINE DERIVATIVE
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP1295873A1

  公开（公告）日：2003-03-26

  Disclosed are a method for producing racemic piperidine derivatives by processing optically-active piperidine derivatives in a hydrogen atmosphere in the presence of a reducing catalyst; and a method for producing optically-active piperidine derivatives or their acid salts by optically resolving the racemic piperidine derivatives obtained in the former method.

  本发明公开了一种生产外消旋哌啶衍生物的方法，该方法是在氢气环境中，在还原催化剂的存在下处理光学活性哌啶衍生物；以及一种生产光学活性哌啶衍生物或其酸盐类的方法，该方法是对前一种方法中获得的外消旋哌啶衍生物进行光学解析。
• Processes for producing racemic piperidine derivative and for producing optically active piperidine derivative
  申请人：——

  公开号：US20030130313A1

  公开（公告）日：2003-07-10

  Disclosed are a method for producing racemic piperidine derivatives by processing optically-active piperidine derivatives in a hydrogen atmosphere in the presence of a reducing catalyst; and a method for producing optically-active piperidine derivatives or their acid salts by optically resolving the racemic piperidine derivatives obtained in the former method.

  本发明公开了一种生产外消旋哌啶衍生物的方法，该方法是在氢气环境中，在还原催化剂的存在下处理光学活性哌啶衍生物；以及一种生产光学活性哌啶衍生物或其酸盐类的方法，该方法是对前一种方法中获得的外消旋哌啶衍生物进行光学解析。
• [EN] PHOSPHAMIDE DERIVATIVE, METHOD FOR MANUFACTURING THE SAME, AND USES THEREOF<br/>[FR] DÉRIVÉ DE PHOSPHAMIDE, SON PROCÉDÉ DE FABRICATION ET SES UTILISATIONS<br/>[ZH] 一种磷酰胺衍生物及制备方法和用途
  申请人：SICHUAN HAISCO PHARMACEUTICAL CO LTD

  公开号：WO2017133517A1

  公开（公告）日：2017-08-10

  公开了一种磷酰胺衍生物及制备方法和用途。特别公开了一种通式(I)所示化合物及其药学上可接受的盐或立体异构体 (I)，其中，G、L、Q、s如说明书中所定义。