n-Methyl-2-phenyl-n-[(5r,7s,8s)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]dec-8-yl]acetamide

Base Information

• Chemical Name: n-Methyl-2-phenyl-n-[(5r,7s,8s)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]dec-8-yl]acetamide
• CAS No.: 96744-75-1
• Molecular Formula: C₂₂H₃₂N₂O₂
• Molecular Weight: 356.508
• UNII: J5S4K6TKTG
• DSSTox Substance ID: DTXSID3046326
• Nikkaji Number: J257.581G
• Wikipedia: U-69,593
• Wikidata: Q7862883
• Pharos Ligand ID: GUXAR8T73J89
• Metabolomics Workbench ID: 66388
• ChEMBL ID: CHEMBL440765
• Mol file: 96744-75-1.mol

Synonyms:N-methyl-N-(7-(1-pyrrolidinyl)-1-oxaspiro(4,5)dec-8-yl)benzeneacetamide;U 69593;U-69593

Chemical Property of n-Methyl-2-phenyl-n-[(5r,7s,8s)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]dec-8-yl]acetamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 120-123℃
• Boiling Point: 518.7°Cat760mmHg
• PKA: 9.15±0.20(Predicted)
• Flash Point: 267.5°C
• PSA: 32.78000
• Density: 1.13g/cm³
• LogP: 3.19150
• Storage Temp.: 2-8°C
• Solubility.: H2O: 14 mg/mL
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 356.246378268
• Heavy Atom Count: 26
• Complexity: 485

Purity/Quality:

98%,99%, ^*data from raw suppliers

U-69593 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C1CCC2(CCCO2)CC1N3CCCC3)C(=O)CC4=CC=CC=C4
• Isomeric SMILES: CN([C@H]1CC[C@@]2(CCCO2)C[C@@H]1N3CCCC3)C(=O)CC4=CC=CC=C4
• Uses: U-69593 is a selective κ-opioid receptor agonist. A safe opioid analgesic.
• Biological Functions: U-69593 is a single enantiomer with very high selectivity for the kappa receptor in vitro (mu/kappa ratio = 484). It was radiolabelled by a catalytic exchange of tritium for the two aromatic chlorine substituents of the precursor. This ligand is commercially available and has been widely used as a radiolabel for the kappa receptor.in spinal cordslice preparations from the 9-16-day-old rat,U-69593 produced a na-loxone-reversible depression of spontaneous and electrically evoked activityin dorsal horn neurones.

Technology Process of n-Methyl-2-phenyl-n-[(5r,7s,8s)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]dec-8-yl]acetamide

There total 1 articles about n-Methyl-2-phenyl-n-[(5r,7s,8s)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]dec-8-yl]acetamide 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: 91.0%

(-)-(5α,7α,8β)-N-methyl-N-7-(1-pyrrolidinyl)-1-oxaspiro<4,5>decan-8-amine (1033267-82-1) + phenylacetyl chloride (103-80-0) → N-methyl-2-phenyl-N-[(5R,7S,8S)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]dec-8-yl]acetamide (90214-48-5,90244-68-1,96744-75-1,117677-65-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1055/s-2008-1032185

upstream raw materials:

(-)-(5α,7α,8β)-N-methyl-N-7-(1-pyrrolidinyl)-1-oxaspiro<4,5>decan-8-amine

phenylacetyl chloride

Refernces