4-Phenyl-1,2,3,6-tetrahydropyridine

Base Information

• Chemical Name: 4-Phenyl-1,2,3,6-tetrahydropyridine
• CAS No.: 10338-69-9
• Molecular Formula: C11H13N
• Molecular Weight: 159.231
• Hs Code.: 2933399090
• European Community (EC) Number: 676-256-8
• NSC Number: 54451
• DSSTox Substance ID: DTXSID2065040
• Nikkaji Number: J257.553A
• Wikidata: Q72506542
• Pharos Ligand ID: G8R26BBQHNS4
• ChEMBL ID: CHEMBL6224
• Mol file: 10338-69-9.mol

Synonyms:4-phenyl-1,2,3,6-tetrahydropyridine;4-phenyl-1,2,3,6-tetrahydropyridine hdyrochloride

Chemical Property of 4-Phenyl-1,2,3,6-tetrahydropyridine

Chemical Property:

• Boiling Point: 267.923 °C at 760 mmHg
• PKA: 9.41±0.10(Predicted)
• Flash Point: 119.944 °C
• PSA: 12.03000
• Density: 1.008 g/cm³
• LogP: 3.19410
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 159.104799419
• Heavy Atom Count: 12
• Complexity: 166

Purity/Quality:

97% ^*data from raw suppliers

4-Phenyl-1,2,3,6-tetrahydropyridine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36-51
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC=C1C2=CC=CC=C2

Technology Process of 4-Phenyl-1,2,3,6-tetrahydropyridine

There total 24 articles about 4-Phenyl-1,2,3,6-tetrahydropyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

4-hydroxy-4-phenylpiperidine-1-carboxylic acid tert-butyl ester (172734-33-7) → 1,2,3,6-tetrahydro-4-phenylpyridine (10338-69-9)

Guidance literature:

With trifluoroacetic acid; for 1h; Reflux;

DOI:10.1039/c6dt01461e

Reference yield: 68.0%

4-hydroxy-4-phenylpiperidin (40807-61-2) → 1,2,3,6-tetrahydro-4-phenylpyridine (10338-69-9)

Guidance literature:

With hydrogenchloride; at 80 ℃; for 24h;

DOI:10.1016/j.bmcl.2012.09.080

Reference yield: 56.0%

p-phenylpyridine (939-23-1) → 1,2,3,6-tetrahydro-4-phenylpyridine (10338-69-9)

Guidance literature:

With triphenylborane; diphenylsilane; diphenylamine; In toluene; at 130 ℃; for 24h; chemoselective reaction; Glovebox; Inert atmosphere;

DOI:10.1002/anie.201702304

upstream raw materials:

6-methyl-6-phenyl-[1,3]oxazinane

sodium proprionate

4-bromo-4-phenyl-piperidine; hydrobromide

propionic acid

Downstream raw materials:

p-phenylpyridine

4-phenylpiperidine

4-bromo-4-phenyl-piperidine; hydrobromide

N-(4-phenyl-1,2,3,6-tetrahydropyridin-1-ylmethyl)phthalimide

Refernces

Enhancing a CH-π interaction to increase the affinity for 5-HT _1A receptors

10.1021/ml4004843

The research aimed to explore how modifying the chemical structure of certain compounds could enhance their binding affinity for 5-HT1A receptors, which are important in the central nervous system and targeted by various drugs. 4-Phenyl-1,2,3,6-tetrahydropyridine (THP) is a key chemical structure that was explored for its potential to enhance binding affinity to 5-HT1A receptors compared to its corresponding 4-phenylpiperazine analogues. The study hypothesized that the higher affinity of THP analogues could be attributed to an electrostatic interaction between the distal phenyl ring of the molecule and a phenylalanine residue (Phe 6.52) in the 5-HT1A receptor binding pocket. This interaction is believed to be stabilized by an edge-to-face CH-p interaction, where the phenyl ring of the THP compound and the phenyl ring of the Phe 6.52 residue are almost coplanar. The results showed that the presence of electron-donating groups, particularly two methyl groups in positions 3 and 5, significantly increased the affinity for 5-HT1A receptors. The study concluded that the THP structure, when appropriately substituted, can enhance the CH-p interaction and improve receptor binding, providing valuable insights for the design of high-affinity 5-HT1A ligands.