59349-71-2

Basic information

• Product Name: (S)-3-phenylpiperidine
• Synonyms: Einecs 261-713-2;(3S)-3-Phenylpiperidine;Piperidine, 3-phenyl-, (3S)-
• CAS NO: 59349-71-2
• Molecular Formula: C₁₁H₁₅N
• Molecular Weight: 161.25
• EINECS: 261-713-2
• Mol File: 59349-71-2.mol

Chemical Properties

• Boiling Point: 263℃
• Flash Point: 116℃
• Appearance: /
• Density: 0.967
• Vapor Pressure: 0.0104mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: 2-8°C(protect from light)
• PKA: 10.01±0.10(Predicted)
• CAS DataBase Reference: (S)-3-phenylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-phenylpiperidine(59349-71-2)
• EPA Substance Registry System: (S)-3-phenylpiperidine(59349-71-2)

Safety Data

• Hazardous Substances Data: 59349-71-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-Phenylpiperidine is used as a key component in the development of new drugs and pharmaceutical products due to its unique chiral structure, which may contribute to novel therapeutic effects and mechanisms of action.
Used in Medicinal Chemistry Research:
(S)-3-Phenylpiperidine is utilized as a research molecule for exploring its potential in medicinal chemistry, where its specific arrangement of atoms can be studied to understand its interactions with biological targets and its potential as a precursor to other pharmaceutically relevant compounds.
Used in Organic Synthesis:
(S)-3-Phenylpiperidine is used as a building block in organic synthesis, providing a foundation for the preparation of more complex chemical compounds that may have various applications in the chemical industry and beyond.

InChI:InChI=1/C11H15N/c1-2-5-10(6-3-1)11-7-4-8-12-9-11/h1-3,5-6,11-12H,4,7-9H2/t11-/m1/s1

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 58879-07-5 N-benzyl-3-hydroxy-3-phenylpiperidine 
• 40114-49-6 1-benzyl-3-piperidone 
• 100-59-4 phenylmagnesium chloride 
• 3979-67-7 N-benzyl-3-phenylpiperidine 
• 3973-62-4 3-phenylpiperidine 

Downstream Products

• 1335523-82-4 4-(3S-piperidine-3-yl)bromobenzene 
• 1476776-55-2 (S)-3-(4-bromophenyl)piperidine-1-carboxylic acid tert-butyl ester 
• 1448668-30-1 C₃₂H₃₆N₂O₃ 
• 1448667-84-2 (2'S,3S,4'S)-1^,-(2,2-diphenylacetyl)-3-phenyl-[1,4'-bipiperidine]-2'-carboxylic acid 
• 1448668-29-8 C₃₂H₃₆N₂O₃ 
• 1448667-83-1 (2'S,3S,4'R)-1^,-(2,2-diphenylacetyl)-3-phenyl-[1,4'-bipiperidine]-2'-carboxylic acid 
• 1246348-09-3 cyclohexyl-{3-[3-((S)-3-phenyl-piperidin-1-yl)-propyl]-1H-pyrazolo[4,3-c]pyridin-4-yl}-amine 
• 1446654-09-6 C₃₁H₃₄N₂O₃ 

Relevant articles and documents

Synthesis method for (R)-3-phenylpiperidine or/and (S)-3-phenylpiperidine and synthesis method for chiral intermediate of niraparib

The invention belongs to the technical field of organic synthesis. The synthesis method firstly provided by the invention takes benzyl-4-oxopiperidine as a starting material, and the starting materialis subjected to Grignard reaction, elimination reaction, hydrogenation reduction reaction and chiral resolution in sequence to successfully obtain a target product (R)-3-phenylpiperidine or/ and (S)-3-phenylpiperidine. The synthesis method sencondly provided by the invention takes the same starting raw material for Grignard reaction, organic silicon reagent is used for removing a hydroxide radical, and benzyl is removed by catalytic hydrogenation reaction; finally, the chiral resolution is carried out to obtain a target product. The (S)-3-phenylpiperidine can be synthesized according to the synthesis method. (S)-3-p-aminosalicylic phenylpiperidine can be synthesized according to the third aspect; or according to the fourth aspect, (S)-3-p-bromophenyl piperidine is synthesized to serve asthe key intermediate for preparing the niraparib. According to the synthesis method for (R)-3-phenylpiperidine or/ and (S)-3-phenylpiperidine and the synthesis method for chiral intermediate of niraparib, production cost is obviously lowered, and the synthesis methods are favorable for the large-scale industrial production of a niraparib medicine.

On the quantitative structure-activity relationships of meta-substituted (S)-phenylpiperidines, a class of preferential dopamine D2 autoreceptor ligands: Modeling of dopamine synthesis and release in vivo by means of partial least squares regression

The quantitative structure-activity relationship between physicochemical properties and effects on dopamine (DA) synthesis and release in the rat brain, in a series of meta-substituted (S)phenylpiperidines, has been investigated by means of partial least squares regression (PLS). The effect on DA synthesis caused by the drugs, in both non-pretreated and reserpine- pretreated rats, was assessed by measurements of tissue levels of L-DOPA accumulated in the striatum following treatment with a decarboxylase inhibitor. Assessment of effects on DA release was performed by analysis of perfusates collected from implanted microdialysis probes. The numerical characterization of the variation in physicochemical features of the phenylpiperidines used in the regression modeling was accomplished by using common tabulated aromatic and aliphatic substituent constants in combination with a set of property descriptors derived from molecular mechanics and semiempirical calculations. It was found that the biochemical responses could be accurately predicted by the regression models based on these molecular feature measures. The molecular features exerting influence an DA synthesis were found to be markedly different from those influencing DA release. This finding is discussed in terms of the possible existence of a dopamine receptor-mediated DA release-controlling mechanism, which may not involve the synthesis regulating DA D2 autoreceptor. Some findings regarding the impact of the piperidine N substituent on agonist properties of the drugs are reported. The regression models were also used for guidance in the search for a phenylpiperidine with a lower intrinsic activity, at the DA D2 type autoreceptor, than the partial DA agonist preclamol (3).