4-(4-甲氧基苯基)哌啶 | 67259-62-5

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-(4-甲氧基苯基)哌啶
• 中文别名: 4-(2-甲氧基苯基)哌啶；4-(4-甲基苯基)哌啶
• 英文名称: 4-(4-methoxyphenyl)piperidine
• CAS: 67259-62-5
• 化学式: C₁₂H₁₇NO
• mdl: MFCD03839927
• 分子量: 191.273
• InChiKey: VCRQRAYQLAPLJH-UHFFFAOYSA-N

物化性质

• 沸点：
  304℃
• 密度：
  1.003
• 闪点：
  122℃

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 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：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  1-苄基-4-(4-甲氧基苯基)四氢吡啶	N-benzyl-4-(4-methoxyphenyl)piperidine	13314-69-7	C19H23NO	281.398
  ——	tert-butyl 4-(4-methoxyphenyl)piperidine-1-carboxylate	303975-71-5	C17H25NO3	291.39
  1-苄氧羰基-4-(4-甲氧基苯基)哌啶	benzyl 4-(4-methoxyphenyl)piperidine-1-carboxylate	127625-95-0	C20H23NO3	325.408
  1-Boc-4-对羟基苯基哌啶	tert-butyl 4-(4-hydroxyphenyl)piperidine-1-carboxylate	149377-19-5	C16H23NO3	277.364

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	1-methoxymethyl-4-(4-methoxy-phenyl)-piperidine	946429-26-1	C14H21NO2	235.326
  ——	4-(4-butoxyphenyl)-1-propylpiperidine	1369588-99-7	C18H29NO	275.434
  2-[4-(4-甲氧基苯基)哌啶-1-基]-N-(3-甲基苯基)乙酰胺	2-[4-(4-Methoxyphenyl)piperidin-1-yl]-N-(3-methylphenyl)acetamide	918408-41-0	C21H26N2O2	338.45

反应信息

• 作为反应物：
  描述：

  4-(4-甲氧基苯基)哌啶 在 盐酸 、 sodium hydroxide 、 potassium carbonate 作用下， 反应 24.83h， 生成 2-[2-[2-[4-(4-methoxyphenyl)piperidin-1-yl]ethoxy]phenyl]-N-methyl-1,3-thiazolidine-3-carbothioamide
  参考文献：
  名称：

  Synthesis of 2-phenylthiazolidine derivatives as cardiotonic agents. IV. Modification of the phenylpiperazino moiety of 2-(phenylpiperazinoalkoxyphenyl)thiazolidine-3-carbothioamides and the corresponding carboxamides.

  摘要：

  通过对苯基哌嗪分子进行化学修饰，扩展了作为新型强心剂的 2-（苯基哌嗪烷氧基苯基）-噻唑烷-3-硫代酰胺和相应羧酰胺（1）的结构-活性关系研究。从氯化物（10）通过几个中间体（12、14 和 16）制备出了 4-苯基哌啶（13）、4-苯基四氢吡啶（17）和相关衍生物，并进行了强心活性测试。一般来说，4-苯基哌啶（13）和 4-苯基四氢吡啶（17）衍生物都表现出与 1 相似的强效正性肌力活性，而 N-苯基哌啶（9）和酰胺衍生物（22、25 和 28）则没有表现出明显的正性肌力活性。苯基丙胺（29）和乙二胺（30）的情况也是如此，它们是 1 的哌嗪分子的假环类似物。均哌嗪衍生物（23）的活性约为相应哌嗪衍生物（1）的三十分之一。因此，在这一系列化合物中，烷氧基侧链末端含有 4-苯基基团的六元碱性氮杂环烷环（哌啶或哌嗪）似乎是产生强效正性肌力活性的关键。

  DOI：

  10.1248/cpb.35.2825
• 作为产物：
  描述：

  1-benzyl-4-(4-methoxy-phenyl)-1,2,3,6-tetrahydro-pyridine 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、393.01 kPa 条件下， 反应 24.0h， 以96%的产率得到4-(4-甲氧基苯基)哌啶
  参考文献：
  名称：

  Design, syntheses, and characterization of pharmacophore based chemokine receptor CCR5 antagonists as anti prostate cancer agents

  摘要：

  Accumulating evidence has shown multiple roles that chemokine receptor CCR5 may play to promote the progression of several types of cancer. The mechanism of such promotion is believed to involve chronic inflammation that creates a microenvironment which enhances tumor survival. Therefore, blocking CCR5 function with an antagonist may provide a novel treatment of cancers such as prostate cancer. Currently, several CCR5 antagonists are available, but all have been optimized for their inhibitory activity on HIV-1 cellular membrane invasion process rather than inhibition on cytoplasmic signaling pathways. Thus, there is need to develop CCR5 antagonists focusing on blockage of CCR5 downstream signaling and inhibition of CCR5 related prostate cancer proliferation and progression. In this report, a pharmacophore analysis was conducted based on docking studies of several known CCR5 antagonists in a CCR5 homology model. A unique structural skeleton for CCR5 antagonist was constructed and functionalized, resulting in a new series of small molecules to be synthesized and characterized. A combination of CCR5 calcium flux inhibition, anti prostate cancer cell proliferation, basal cytotoxicity, and in vivo animal model studies were applied to screen the newly synthesized compounds. Results from this study provided a potential lead compound for future CCR5 antagonist development focusing on prostate cancer therapy. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.09.004

文献信息

• Substituted piperidines as therapeutic compounds
  申请人：Speedel Experimenta AG

  公开号：EP2018862A1

  公开（公告）日：2009-01-28

  Described are compounds of the general formula (I) and pharmaceutically acceptable salt thereof, in which R2, R3, W,and X have the definitions illustrated in detail in the description, as beta-secretase, cathepsin D, plasmepsin II and/or HIV protease inhibitors.

  描述了一般式（I）的化合物及其药用可接受的盐，其中R2、R3、W和X的定义在描述中详细说明，作为β-分泌酶、半胱氨酸蛋白酶D、质体蛋白酶II和/或HIV蛋白酶抑制剂。
• Selective NR2B Antagonists
  申请人：Bristol-Myers Squibb Company

  公开号：US20150191452A1

  公开（公告）日：2015-07-09

  The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands of the NR2B receptor and may be useful for the treatment of various disorders of the central nervous system.

  该披露通常涉及到I式化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物是NR2B受体的配体，可能对治疗中枢神经系统的各种疾病有用。
• Compounds having effects on serotonin-related systems
  申请人：Eli Lilly and Company

  公开号：US05741789A1

  公开（公告）日：1998-04-21

  A series of hetero-oxy alkanamines are effective pharmaceuticals for the treatment of conditions related to or affected by the reuptake of serotonin and by the serotonin 1.sub.A receptor. The compounds are particularly useful for alleviating the symptoms of nicotine and tobacco withdrawal, and for the treatment of depression and other conditions for which serotonin reuptake inhibitors are used.

  一系列的杂氧烷胺类化合物是治疗与血清素再摄取和血清素1A受体有关或受其影响的疾病的有效药物。这些化合物特别适用于缓解尼古丁和烟草戒断症状，以及治疗抑郁症和其他需要使用血清素再摄取抑制剂的疾病。
• [EN] COMPOUNDS AND COMPOSITIONS AS MODULATORS OF GPR119 ACTIVITY<br/>[FR] COMPOSÉS ET COMPOSITIONS EN TANT QUE MODULATEURS DE L'ACTIVITÉ DE GPR119
  申请人：IRM LLC

  公开号：WO2009038974A1

  公开（公告）日：2009-03-26

  The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of GPR119.

  这项发明提供了化合物，包括这些化合物的药物组合物以及使用这些化合物治疗或预防与GPR119活性相关的疾病或紊乱的方法。
• [EN] 20-HETE FORMATION INHIBITORS<br/>[FR] INHIBITEURS DE FORMATION DE 20-HETE
  申请人：UNIV OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：WO2020163689A1

  公开（公告）日：2020-08-13

  This disclosure provides novel heterocyclic compounds and methods for inhibiting the enzyme CYP4. Further disclosed methods include: a method of inhibiting the biosynthesis of 20-hydroxyeicosatetraenoic acid (20-HETE) in a subject in need thereof and a method of producing neuroprotection and decreased brain damage by preventing cerebral microvascular blood flow impairment and anti-oxidant mechanisms in a subject experiencing or having experienced an ischemic event.

  本公开提供了新颖的杂环化合物和抑制酶CYP4的方法。进一步公开的方法包括：一种抑制需要该物质的受试者体内20-羟基二十碳五烯酸（20-HETE）生物合成的方法，以及通过防止脑微血管血流受损和抗氧化机制来产生神经保护和减少脑损伤的方法，适用于正在经历或曾经经历缺血事件的受试者。