1-(2-甲氧基苯基)-4-(2-苯基乙基)哌嗪 | 144146-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(2-甲氧基苯基)-4-(2-苯基乙基)哌嗪
• 英文名称: 1-(2-methoxyphenyl)-4-(2-phenyl-1-ethyl)piperazine
• 英文别名: 1-(2-methoxyphenyl)-4-(2-phenylethyl)piperazine；1-(2-phenylethyl)-4-(2-methoxyphenyl)piperazine；4-(phenylethyl)-1-(2-methoxyphenyl)piperazine；1-(2-methoxyphenyl)-4-phenethylpiperazine；LDT2；Piperazine, 1-(2-methoxyphenyl)-4-(2-phenylethyl)-
• CAS: 144146-62-3
• 化学式: C₁₉H₂₄N₂O
• 分子量: 296.412
• InChiKey: AMBPIKSQPHQYTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  432.7±45.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)
• 溶解度：
  37.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2-甲氧苯基)哌嗪 、 乙基溴苯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.07h， 以93%的产率得到1-(2-甲氧基苯基)-4-(2-苯基乙基)哌嗪
  参考文献：
  名称：

  新型芳基哌嗪作为α1-肾上腺素受体有效拮抗剂的合成及其构效关系

  摘要：

  芳基哌嗪2 - 11合成，和它们在通过结合表达人克隆亚型的CHO细胞测定法评估α1肾上腺素能受体（α1-ARS），并通过在分离的大鼠输精管功能性实验（α1A），脾（α1B）生物型材，和主动脉（α1D）。在结合实验中，对1,3-苯并二恶唑和苯基正电单元的修饰导致鉴定出许多有效的化合物（相对于α1b-AR具有中等选择性）。值得注意的是，化合物7（LDT451）显示出亚纳摩尔p K i朝向α1a-AR的9.41。对于所有系列化合物而言，令人鼓舞的是较低的α1B效能是一个总体趋势，在功能测定中，α1A/ D的选择性超过了α1B的选择性。如果充分优化，这种特殊的选择性可能与潜在的LUTS / BPH治疗应用有关。

  DOI：

  10.1016/j.ejmech.2016.06.052

文献信息

• Base-catalyzed hydroamination of aromatic olefins-an efficient route to 1-aryl-4-(arylethyl)piperazines
  作者：Matthias Beller、Claudia Breindl

  DOI：10.1016/s0040-4020(98)00295-6

  日期：1998.6

  An efficient synthesis of pharmaceutically interesting 1-aryl-4-(arylethyl)piperazines by base-catalyzed hydroamination is presented. Starting from substituted aryl olefins and various N-arylpiperazines, the desired products 3 – 12 were obtained in one step under mild conditions in the presence of a catalytic amount of n-butyllithium in yields up to 99%.

  提出了一种通过碱催化的加氢胺化反应来有效合成可药用的1-芳基-4-（芳基乙基）哌嗪的方法。从取代的芳基烯烃和各种起始Ñ -arylpiperazines，所需产物12 - 3在催化量的存在下在温和条件下一个步骤获得Ñ丁基锂在产率高达99％。
• Synthesis of Several Substituted Phenylpiperazines Behaving as Mixed D2/5HT1A Ligands
  作者：Sladjana Dukić、Sladjana Kostić-Rajačić、Deana Dragović、Vukic Šoškić、Jelena Joksimović

  DOI：10.1111/j.2042-7158.1997.tb06037.x

  日期：2011.4.12

  N-4 nitrogen to dopaminergic pharmacophores of the 2-(5-benzimidazole)ethyl-, 2-(5-benztriazole)ethyl-, 2-[5-(benzimidazole-2-thione)]ethyl- and 2-[6-(1,4-dihydroquinoxaline-2,3-dione)]ethyl-type were selected according to known structure-affinity requirements of 1-arylpiperazines. All the new compounds were evaluated for in-vitro binding affinity at the dopamine (D1 and D2) and 5-HT1A receptors. Synaptosomal

  为了产生新的混合的D2 / 5HT1A配体，已合成了22种不同的化合物。为此，通过N-4氮与2-（5-苯并咪唑）乙基-，2-（5-苯并三唑）乙基-，2- [5-（苯并咪唑-2-硫酮）的多巴胺能药效团连接的1-取代的苯基哌嗪根据1-芳基哌嗪的已知结构亲和性要求选择）]乙基和2- [6-（1,4-二氢喹喔啉-2,3-二酮）]乙基类型。评价所有新化合物对多巴胺（D1和D2）和5-HT1A受体的体外结合亲和力。由新鲜牛尾状核和海马体制备的突触体膜分别用作多巴胺和5-羟色胺受体的来源。[3H] SCH 23390（D1选择性），将[3H]哌隆（D2选择性）和8-OH- [3H] DPAT（5-HT1A选择性）用作放射性配体。这些化合物均未表达对D1多巴胺受体结合的亲和力。化合物3b和4b在8-OH- [3H] DPAT竞争剂中是无效的，而1b，2b和4b在[3H]哌啶结合测定中是无活性的。测试的其他
• Use of Adrenergic N-Phenylpiperazine Antagonists, Pahrmaceutical Compositions Containning Them, and Methods of Preparing Them
  申请人：Soares Romeiro Antonio Luiz

  公开号：US20070219213A1

  公开（公告）日：2007-09-20

  The present invention describes phenylpiperazinyl alpha adrenergic antagonists that corresponds to the formula (I) which selectively act on the alpha 1A/alpha 1D subtypes, where its selectivity index in comparison to alpha 1B subtype is, at minimum, 1700 for the alpha 1A subtype and 10000 for the alpha 1 D subtype, being therefore useful for the treatment of the lower urinary tract symptoms, including the benign prostatic hyperplasia treatment in mammals, preferentially humans. It is also described pharmaceutical compositions containing said compounds and methods for its preparation.

  本发明描述了与公式（I）相对应的苯基哌嗪基α肾上腺素受体拮抗剂，其选择性作用于α1A/α1D亚型，其中与α1B亚型相比的选择性指数，对于α1A亚型至少为1700，对于α1D亚型至少为10000，因此可用于治疗哺乳动物，尤其是人类的下尿路症状，包括良性前列腺增生的治疗。还描述了含有该化合物的药物组合物以及其制备方法。
• Base-catalyzed synthesis of 1-aryl-4-(aryl ethyl)piperazines from aromatic olefins and 1-arylpiperazines
  申请人：Aventis Research & Technologies

  公开号：US06313297B1

  公开（公告）日：2001-11-06

  A process for preparing a 1-aryl-4-(arylethyl)piperazine of the formula (I) by reacting a 1-arylpiperazine of the formula (II) with an aromatic olefin of the formula (III) Ar′CR1═CHR2  (III) in an inert solvent in the presence of at least one basic catalyst, where in the formulae (I) to (III) Ar and Ar′ independently of one another are an aryl radical, selected from the group of the fused and unfused C6-C22-aromatics and the fused or unfused C5-C22-heteroaromatics which have at least one nitrogen, oxygen or sulfur atom in the ring; and R1 and R2 independently of one another are a hydrogen atom, a C1-C8-alkyl radical or an aryl radical Ar.

  一种制备式(I)的1-芳基-4-(芳基乙基)哌嗪的方法，通过在惰性溶剂中，在至少一个碱性催化剂的存在下，将式(II)的1-芳基哌嗪与式(III)的芳香烯烃Ar′CR1═CHR2反应而得，其中在式(I)到(III)中，Ar和Ar′分别是取自融合和未融合的C6-C22芳香族和至少有一个氮、氧或硫原子在环中的融合或未融合的C5-C22杂环芳香族的芳基基团；而R1和R2分别是氢原子，C1-C8烷基基团或芳基基团Ar。
• The First Rhodium-Catalyzed Anti-Markovnikov Hydroamination: Studies on Hydroamination and Oxidative Amination of Aromatic Olefins
  作者：M. Beller、H. Trauthwein、M. Eichberger、C. Breindl、J. Herwig、T. E. Müller、O. R. Thiel

  DOI：10.1002/(sici)1521-3765(19990401)5:4<1306::aid-chem1306>3.0.co;2-4

  日期：1999.4.1

  The first transition-metal-catalyzed regiospecific anti-Markovnikov hydroamination of aromatic olefins is reported. Styrene and substituted styrenes react with secondary aliphatic amines, especially morpholine and N-arylpiperazines, in the presence of cationic rhodium complexes to give 2-aminoethenylbenzene and 2-aminoethylbenzene derivatives. Cationic [Rh(cod)(2)]+BF4- and various phosphines (1:2-mixture) were employed as in situ catalysts. According to labeling experiments, there is no evidence that the hydroamination is a consecutive hydrogenation of a previously formed enamine. Hydroamination with simple secondary amines, for example piperidine, can also be achieved by the use of a higher olefin concentration and higher reaction temperatures than those given in previously published reaction procedures. Kinetic investigations of the major reaction pathway reveal that the reaction rate of the oxidative amination and the hydroamination is dependent on the styrene and on the catalyst concentration, and independent of the amine concentration. Experiments that employed deuterium-labeled amines (N-D) provided evidence that the mechanism involves an amine-activating pathway, The substituents on the styrene, the phosphine ligand, and the solvent influence the yield of the aminations and the enamine:alkylamine ratio.