1-(1-苯基环己基)-4-羟基哌啶 | 60232-85-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-(1-苯基环己基)-4-羟基哌啶
• 英文名称: 1-(1-phenylcyclohexyl)-4-hydroxypiperidine
• 英文别名: PHP；(1-phenylcyclohexyl)-4-hydroxypiperidine；1-(1-phenyl-cyclohexyl)-piperidin-4-ol；(1-phenylcyclohexyl) 4-hydroxypiperidine；1-(1-phenylcyclohexyl)piperidin-4-ol
• CAS: 60232-85-1
• 化学式: C₁₇H₂₅NO
• 分子量: 259.392
• InChiKey: SLUMSLWGPLFKGY-UHFFFAOYSA-N

物化性质

• 熔点：
  116-118 °C(Solv: hexane (110-54-3); ethanol (64-17-5))
• 沸点：
  400.9±25.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：30mg/mL； DMF:PBS(pH 7.2)(1:6)：0.14 mg/ml； DMSO：25mg/mL；乙醇：30mg/mL
• 保留指数：
  2550

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

PCHP是已知的人体代谢物，由苯环利定（PCP）代谢产生。

PCHP is a known human metabolite of phencyclidine.

来源:NORMAN Suspect List Exchange

安全信息

• 储存条件：
  -20°C，密闭保存，并保持干燥。

制备方法与用途

(1-苯基环己基)-4-羟哌啶是一种结构分类为芳基环己胺的分析标准品。

反应信息

• 作为反应物：
  描述：

  1-(1-苯基环己基)-4-羟基哌啶 在 aluminum isopropoxide 作用下， 以 丙酮 、 苯 为溶剂， 反应 7.0h， 以25%的产率得到1-(1-phenylcyclohexyl)-4-piperidone
  参考文献：
  名称：

  衍生自苯环利定的新型止痛药。

  摘要：

  1-（1-苯基环己基）-4-哌啶醇（3），1-（1-苯基环己基）-4-苯基-4-哌啶醇（10）及其丙酸酯（11）和1-（1-苯基环己基）的几种酯制备并表征了）-4-苯基哌啶（13）。衍生自苯环利定的新化合物在小鼠中发挥镇痛作用。最有效的是10，活性是吗啡的两倍。10、11和13的抗伤害感受活性可能与它们在小鼠输精管生物测定中的功效密切相关，并且纳洛酮可完全逆转两者。

  DOI：

  10.1021/jm00137a004
• 作为产物：
  描述：

  4-hydroxypiperidinocyclohexyl carbonitrile 在 吡啶 、 magnesium 、 六甲基二硅氮烷 作用下， 反应 6.0h， 生成 1-(1-苯基环己基)-4-羟基哌啶
  参考文献：
  名称：

  衍生自苯环利定的新型止痛药。

  摘要：

  1-（1-苯基环己基）-4-哌啶醇（3），1-（1-苯基环己基）-4-苯基-4-哌啶醇（10）及其丙酸酯（11）和1-（1-苯基环己基）的几种酯制备并表征了）-4-苯基哌啶（13）。衍生自苯环利定的新化合物在小鼠中发挥镇痛作用。最有效的是10，活性是吗啡的两倍。10、11和13的抗伤害感受活性可能与它们在小鼠输精管生物测定中的功效密切相关，并且纳洛酮可完全逆转两者。

  DOI：

  10.1021/jm00137a004

文献信息

• Application of chemical P450 model systems to studies on drug metabolism. I. Phencyclidine. A multi-functional model substrate.
  作者：Hiroshi MASUMOTO、Kaoru TAKEUCHI、Shigeru OHTA、Masaaki HIROBE

  DOI：10.1248/cpb.37.1788

  日期：——

  Cytochrome P450 model and liver microsomal oxidations of drugs were compared using phencyclidine. In general, the chemical reaction systems produced many oxidation products. Besides the formation of the cyclohexane-4-hydroxyl compound (2), hydroxylation of the aromatic ring was favored in the Fenton reaction system (Fe2++H2O2). Formation of an m-hydroxylated product (m-5) was the main aromatic oxidation pathway in the Udenfriend reaction (Fe2+-ascorbic acid-O2), and 2, the piperidine-3-hydroxyl compound (3), and the piperidine-4-hydroxyl compound (4) were also formed. In the system using meso-tetraphenylporphinatoiron chloride (Fe(III)TPPC1) with an oxidant, the main product was the piperidine-3-oxo compound (8). In the liver microsomes system, 2, 4, 8, and m-5, which were all generated by the chemical oxidation reactions, were detected as metabolites of phencyclidine. They were formed by cytochrome P450-dependent reactions. Chemical oxidation systems can be used to study drug metabolism; they can reveal some tendencies of the real metabolis reactions, are easy to operate, and yield sufficient amounts of product.

  使用苯环利定比较了细胞色素P450模型和肝微粒体的药物氧化。一般来说，化学反应系统产生了许多氧化产物。除了形成环己烷-4-羟基化合物（2）外，在芬顿反应体系（Fe2++H2O2）中芳香环的羟基化反应被优先生成。在尤登友反应（Fe2+-抗坏血酸-O2）中，形成m-羟基化产物（m-5）是主要的芳香氧化途径，同时也形成了化合物2、哌啶-3-羟基化合物（3）和哌啶-4-羟基化合物（4）。在使用含氧化剂的美索-四苯基卟啉铁氯化物（Fe(III)TPPC1）体系中，主要产物是哌啶-3-氧化物（8）。在肝微粒体系统中，2、4、8和m-5都是通过化学氧化反应生成的苯环利定代谢物，它们是通过细胞色素P450依赖的反应形成的。化学氧化系统可用于研究药物代谢；它们能够揭示一些真实代谢反应的趋势，操作简单，并能产生足够的产物。
• Phencyclidine and phencyclidine metabolites assay, tracers, immunogens
  申请人：Abbott Laboratories

  公开号：US05124457A1

  公开（公告）日：1992-06-23

  The present invention is directed to a fluorescence polarization assay for phencyclidine and phencyclidine derivatives, to the various components needed for preparing and carrying out such an assay, and to methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for making them. The tracers and the immunogens are made from substituted phencyclidine compounds. A fluorescein moiety is included in the tracer, while a poly(amino acid) forms a part of the immunogen. The assay is conducted by measuring the degree of polarization retention of plane polarized light that has been passed through a sample containing antiserum and tracer.

  本发明涉及一种用于苯环丙胺和苯环丙胺衍生物的荧光偏振测定的方法，涉及用于准备和执行此类测定所需的各种组分，以及制备这些组分的方法。具体地，公开了示踪剂、免疫原和抗体，以及制备它们的方法。示踪剂和免疫原由取代苯环丙胺化合物制成。示踪剂中包含荧光基团，而多肽（氨基酸）构成免疫原的一部分。该测定通过测量已通过含有抗血清和示踪剂的样品的偏振保留度的平面偏振光的程度来进行。
• Metabolism of Phencyclidine by Microorganisms
  作者：Charles D. Huffordx、John K. Baker、Alice M. Clark

  DOI：10.1002/jps.2600700210

  日期：1981.2

  A number of microorganisms were screened for their ability to metabolize phencyclidine. Two microorganisms, Beauveria sulfurescens and Cunninghamella echinulata, produced hydroxylated metabolites, which were identified as 1-(1-phenylcyclohexyl)-4-hydroxypiperidine and 4-phenyl-4-piperidinocyclohexanol by high-pressure liquid chromatographic analysis.

  筛选了许多微生物的代谢苯环利定的能力。通过高压液相色谱分析，两种微生物，白僵菌和马鞭草（Cunninghamella echinulata）产生羟基化的代谢产物，它们被鉴定为1-（1-苯基环己基）-4-羟基哌啶和4-苯基-4-哌啶基环己醇。
• Phencyclidine and phencyclidine metabolites assay, tracers, immunogens,
  申请人：Abbott Laboratories

  公开号：US05155212A1

  公开（公告）日：1992-10-13

  The present invention is directed to a fluorescence polarization assay for phencyclidine and phencyclidine derivatives, to the various components needed for preparting and carrying out such an assay, and to methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for making them, and a reagent kit containing them. The tracers and the immunogens are made from substituted phencyclidine compounds. A fluorescein moiety is included in the tracer, while a poly(amino acid) forms a part of the immunogen. The assay is conducted by measuring the degree of polarization retention of plane polarized light that has been passed through a sample containing antiserum and tracer.

  本发明涉及一种用于苯环丙胺和苯环丙胺衍生物的荧光偏振测定法，以及制备和执行此类测定所需的各种组分和制备这些组分的方法。具体而言，本发明揭示了示踪剂、免疫原和抗体，以及制备它们的方法和包含它们的试剂盒。示踪剂和免疫原是由取代苯环丙胺化合物制备而成。示踪剂中包含荧光素基团，而免疫原中包含一种聚（氨基酸）。该测定方法是通过测量通过含有抗血清和示踪剂的样品的偏振平面光的偏振保留度来进行的。
• Phencyclidine and phencyclidine metabolites assay, tracers, immunogens, antibodies and reagent kit
  申请人：ABBOTT LABORATORIES

  公开号：EP0459387A2

  公开（公告）日：1991-12-04

  The present invention is directed to a fluorescence polarization assay for phencyclidine and phencyclidine derivatives, to the various components needed for preparing and carrying out such an assay, and to methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for making them, and a reagent kit containing them. The tracers and the immunogens are made from substituted phencyclidine compounds. A fluorescein moiety is included in the tracer, while a poly(amino acid) forms a part of the immunogen. The assay is conducted by measuring the degree of polarization retention of plane polarized light that has been passed through a sample containing antiserum and tracer.

  本发明涉及苯环利定和苯环利定衍生物的荧光偏振测定法、制备和进行这种测定法所需的各种成分以及制造这些成分的方法。具体而言，本发明公开了示踪剂、免疫原和抗体，以及制造它们的方法和含有它们的试剂盒。示踪剂和免疫原由取代的苯环利定化合物制成。示踪剂中含有荧光素分子，而免疫原中含有聚氨基酸分子。检测方法是测量通过含有抗血清和示踪剂的样品的平面偏振光的偏振保留程度。

表征谱图