(S)-1,4-dibenzyl-2-(2-pyridin-3-ylethyl)piperazine | 612503-27-2

• 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: (S)-1,4-dibenzyl-2-(2-pyridin-3-ylethyl)piperazine
• 英文别名: (S)-1,4-Dibenzyl-2-(2-pyridin-3-yl-ethyl)-piperazine；(2S)-1,4-dibenzyl-2-(2-pyridin-3-ylethyl)piperazine
• CAS: 612503-27-2
• 化学式: C₂₅H₂₉N₃
• 分子量: 371.525
• InChiKey: SQMLMVYNDCPSPT-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1,4-dibenzyl-2-(2-pyridin-3-ylethyl)piperazine 在 palladium on activated charcoal ammonium formate 作用下， 以 乙醇 为溶剂， 以32%的产率得到(2S)-2-[2-(3-吡啶基)乙基]哌嗪
  参考文献：
  名称：

  纯手性 2-(2-芳乙基)哌嗪的合成

  摘要：

  一系列 (S)-2-(2-芳乙基)哌嗪的合成是由 (S)-1,4-dibenzyl-2-vinylpiperazine 通过串联硼氢化/Suzuki 偶联序列然后裂解 N -苄基保护基团。

  DOI：

  10.1055/s-2007-983791
• 作为产物：
  描述：

  (S)-1,4-dibenzyl-2-vinylpiperazine 在 四(三苯基膦)钯 sodium hydroxide 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (S)-1,4-dibenzyl-2-(2-pyridin-3-ylethyl)piperazine
  参考文献：
  名称：

  纯手性 2-(2-芳乙基)哌嗪的合成

  摘要：

  一系列 (S)-2-(2-芳乙基)哌嗪的合成是由 (S)-1,4-dibenzyl-2-vinylpiperazine 通过串联硼氢化/Suzuki 偶联序列然后裂解 N -苄基保护基团。

  DOI：

  10.1055/s-2007-983791

文献信息

• [EN] PIPERAZINE SUBSTITUTED ARYL BENZODIAZEPINES AND THEIR USE AS DOPAMINE RECEPTOR ANTAGONISTS FOR THE TREATMENT OF PSYCHOTIC DISORDERS<br/>[FR] ARYLES BENZODIAZEPINES A SUBSTITUTION DE PIPERAZINE ET LEUR UTILISATION EN TANT QU'ANTAGONISTES DE RECEPTEUR DE DOPAMINE DANS LE TRAITEMENT DE TROUBLES PSYCHOTIQUES
  申请人：LILLY CO ELI

  公开号：WO2003082877A1

  公开（公告）日：2003-10-09

  Described herein are antipyschotic compounds of formula (I) wherein, A is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, O, and S; Alk is (C1-4) alkylene optionally substituted with OH, methoxy, ethoxy, or F; Ar is optionally substituted phenyl, naphthyl, monocyclic heteroaromatic, or bicyclic heteroaromatic; R1 is hydrogen or (C1-4) alkyl optionally substituted with OH, OR3, or OCH2CH2OH, wherein R3 is (C1-2) alkyl; R2 is H, (C1-6) alkyl, halogen, fluorinated (C1-6) alkyl, OR4, SR4, NO2, CN, COR4, CONR5R6, SO2NR5R6, NR5R6, NR5COR4, NR5SO2R4, or optionally substituted phenyl,wherein R4 is hydrogen, (C1-6) alkyl, fluorinated (C1-6) alkyl, benzyl, or optionally substituted phenyl, R5 and R6 are independently hydrogen, (C1-6) alkyl, or optionally substituted phenyl; Z is one or two substituents independently selected from hydrogen, halogen, (C1-6) alkyl, fluorinated (C1-6) alkyl, OR7, SR7, NO2, CN, COR7, CONR8R9, SO2NR8R9, NR8SO2R7, NR8R9, or optionally substituted phenyl, wherein R7 is hydrogen, (C1-6) alkyl, fluorinated (C1-6) alkyl, benzyl, or optionally substituted phenyl, R8 and R9 are independently hydrogen, (C1-6) alkyl, or optionally substituted phenyl; and salts, solvates, and crystal forms thereof. Also described are the use of the compounds of formula (I) as antagonists of the dopamine D2 receptor and as agents for the treatment of psychosis and bipolar disorders, and pharmaceutical formulations of the compounds of formula (I). Also described are compounds useful as intermediates for the synthesis of the compounds of formula (I).

  本文描述了公式（I）的抗精神药物化合物，其中，A是一个可选的苯并嵌有零至三个异原子（N、O和S）的五元或六元芳香环；Alk是（C1-4）烷基烯，可选地取代为OH、甲氧基、乙氧基或F；Ar是可选取代的苯基、萘基、单环杂芳基或双环杂芳基；R1是氢或（C1-4）烷基，可选地取代为OH、OR3或OCH2CH2OH，其中R3是（C1-2）烷基；R2是H、（C1-6）烷基、卤素、氟代（C1-6）烷基、OR4、SR4、NO2、CN、COR4、CONR5R6、SO2NR5R6、NR5R6、NR5COR4、NR5SO2R4或可选取代的苯基，其中R4是氢、（C1-6）烷基、氟代（C1-6）烷基、苄基或可选取代的苯基，R5和R6独立地是氢、（C1-6）烷基或可选取代的苯基；Z是一个或两个取代基，独立地选自氢、卤素、（C1-6）烷基、氟代（C1-6）烷基、OR7、SR7、NO2、CN、COR7、CONR8R9、SO2NR8R9、NR8SO2R7、NR8R9或可选取代的苯基，其中R7是氢、（C1-6）烷基、氟代（C1-6）烷基、苄基或可选取代的苯基，R8和R9独立地是氢、（C1-6）烷基或可选取代的苯基；以及其盐、溶剂合物和晶型。还描述了将公式（I）的化合物用作多巴胺D2受体拮抗剂和治疗精神病和双相障碍的药物，以及公式（I）的化合物的制剂。还描述了作为公式（I）化合物合成的中间体有用的化合物。
• Piperazine substituted aryl benzodiazepines and their use as dopamine receptor antagonists for the treatment of psychotic disorders
  申请人：Aicher Daniel Thomas

  公开号：US20050203296A1

  公开（公告）日：2005-09-15

  Described herein are antipyschotic compounds of formula (I) wherein, A is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, O, and S; Alk is (C 1-4 ) alkylene optionally substituted with OH, methoxy, ethoxy, or F; Ar is optionally substituted phenyl, naphthyl, monocyclic heteroaromatic, or bicyclic heteroaromatic; R 1 is hydrogen or (C 1-4 ) alkyl optionally substituted with OH, OR 3 , or OCH 2 CH 2 OH, wherein R 3 is (C 1-2 ) alkyl; R 2 is H, (C 1-6 ) alkyl, halogen, fluorinated (C 1-6 ) alkyl, OR 4 , SR 4 , NO 2 , CN, COR 4 , CONR 5 R 6 , SO 2 NR 5 R 6 , NR 5 R 6 , NR 5 COR 4 , NR 5 SO 2 R 4 , or optionally substituted phenyl, wherein R 4 is hydrogen, (C 1-6 ) alkyl, fluorinated (C 1-6 ) alkyl, benzyl, or optionally substituted phenyl, R 5 and R 6 are independently hydrogen, (C 1-6 ) alkyl, or optionally substituted phenyl; Z is one or two substituents independently selected from hydrogen, halogen, (C 1-6 ) alkyl, fluorinated (C 1-6 ) alkyl, OR 7 , SR 7 , NO 2 , CN, COR 7 , CONR 8 R 9 , SO 2 NR 8 R 9 , NR 8 SO 2 R 7 , NR 8 R 9 , or optionally substituted phenyl, wherein R 7 is hydrogen, (C 1-6 ) alkyl, fluorinated alkyl, benzyl, or optionally substituted phenyl, R 8 and R 9 are independently hydrogen, (C 1-6 ) alkyl, or optionally substituted phenyl; and salts, solvates, and crystal forms thereof. Also described are the use of the compounds of formula (a) as antagonists of the dopamine D 2 receptor and as agents for the treatment of psychosis and bipolar disorders, and pharmaceutical formulations of the compounds of formula (I). Also described are compounds useful as intermediates for the synthesis of the compounds of formula (I).

  本文描述了式（I）的抗精神病化合物，其中A是一个选择性地与N、O和S中的零到三个杂原子独立选定的五元或六元芳香环，可以与苯并联；Alk是（C1-4）的烷基，可以选择性地用OH，甲氧基，乙氧基或F取代；Ar是选择性取代的苯基，萘基，单环杂芳基或双环杂芳基；R1是氢或（C1-4）烷基，可以选择性地用OH，OR3或OCH2CH2OH取代，其中R3是（C1-2）烷基；R2是H，（C1-6）烷基，卤素，氟化的（C1-6）烷基，OR4，SR4，NO2，CN，COR4，CONR5R6，SO2NR5R6，NR5R6，NR5COR4，NR5SO2R4或选择性取代的苯基，其中R4是氢，（C1-6）烷基，氟化的（C1-6）烷基，苄基或选择性取代的苯基，R5和R6独立地是氢，（C1-6）烷基或选择性取代的苯基；Z是一个或两个取代基，独立选择自氢，卤素，（C1-6）烷基，氟化的（C1-6）烷基，OR7，SR7，NO2，CN，COR7，CONR8R9，SO2NR8R9，NR8SO2R7，NR8R9或选择性取代的苯基，其中R7是氢，（C1-6）烷基，氟化的烷基，苄基或选择性取代的苯基，R8和R9独立地是氢，（C1-6）烷基或选择性取代的苯基；以及其盐，溶剂化合物和晶体形式。本文还描述了将式（a）的化合物用作多巴胺D2受体的拮抗剂以及用于治疗精神病和双相障碍的药物，以及式（I）的化合物的制药配方。还描述了用于合成式（I）的化合物的中间体。
• PIPERAZINE SUBSTITUTED ARYL BENZODIAZEPINES AND THEIR USE AS DOPAMINE RECEPTOR ANTAGONISTS FOR THE TREATMENT OF PSYCHOTIC DISORDERS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1492794B1

  公开（公告）日：2007-12-12
• US7214673B2
  申请人：——

  公开号：US7214673B2

  公开（公告）日：2007-05-08
• Synthesis of Homochiral 2-(2-Arylethyl)piperazines
  作者：John Schaus、Joseph Krushinski、Kevin Ruley、Vincent Rocco

  DOI：10.1055/s-2007-983791

  日期：2007.7

  The synthesis of a series of ( S)-2-(2-arylethyl)piper-azines was achieved from ( S)-1,4-dibenzyl-2-vinylpiperazine via a tandem hydroboration/Suzuki coupling sequence followed by cleavage of the N-benzyl protecting groups.

  一系列 (S)-2-(2-芳乙基)哌嗪的合成是由 (S)-1,4-dibenzyl-2-vinylpiperazine 通过串联硼氢化/Suzuki 偶联序列然后裂解 N -苄基保护基团。