3-(1,3-Dihydro-1-oxo-2h-isoindol-2-yl)-2,6-piperidinedione

Base Information

• Chemical Name: 3-(1,3-Dihydro-1-oxo-2h-isoindol-2-yl)-2,6-piperidinedione
• CAS No.: 26581-81-7
• Deprecated CAS: 103794-93-0
• Molecular Formula: C13H12 N2 O3
• Molecular Weight: 244.25
• European Community (EC) Number: 848-178-6
• DSSTox Substance ID: DTXSID401034323
• Nikkaji Number: J53.848E
• Wikidata: Q26840990
• ChEMBL ID: CHEMBL304572
• Mol file: 26581-81-7.mol

Synonyms:2-(2,6-dioxopiperidin-3-yl)phthalimidine;2-(2,6-dioxopiperidin-3-yl)phthalimidine, (+-)-isomer;2-(2,6-dioxopiperidin-3-yl)phthalimidine, (R)-isomer;2-(2,6-dioxopiperidin-3-yl)phthalimidine, (S)-isomer;2-(2,6-dioxopiperidine-3-yl)phthalimidine;EM 12;EM-12

Chemical Property of 3-(1,3-Dihydro-1-oxo-2h-isoindol-2-yl)-2,6-piperidinedione

Chemical Property:

• Vapor Pressure: 1.72E-11mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 534.3°Cat760mmHg
• PKA: 10.70±0.40(Predicted)
• Flash Point: 276.9°C
• PSA: 69.97000
• Density: 1.393g/cm³
• LogP: 0.66140
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 244.08479225
• Heavy Atom Count: 18
• Complexity: 407

Purity/Quality:

99% ^*data from raw suppliers

PHTHALIMIDINE, 2-(2,6-DIOXOPIPERIDEN-3-YL) 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC(=O)C1N2CC3=CC=CC=C3C2=O
• Description: Phthalimidine, 2-(2,6-dioxopiperiden-3-yl) is a lenalidomide analog that can be useful in PROTAC research.

Technology Process of 3-(1,3-Dihydro-1-oxo-2h-isoindol-2-yl)-2,6-piperidinedione

There total 20 articles about 3-(1,3-Dihydro-1-oxo-2h-isoindol-2-yl)-2,6-piperidinedione 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%

methyl 2-bromomethylbenzoate (2417-73-4) + (+/-)-α-aminoglutarimide (2353-44-8,673485-72-8) → 3-(1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (26581-81-7,103794-93-0,107740-48-7,107657-57-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80 ℃; for 18h;

Reference yield: 90.0%

thalidomide (50-35-1) → 3-(1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (26581-81-7,103794-93-0,107740-48-7,107657-57-8)

Guidance literature:

With tetramethylammonium tetrafluoroborate; tert-butyl alcohol; Trimethylacetic acid; In acetonitrile; at 20 ℃; Solvent; Reagent/catalyst; chemoselective reaction; Electrolysis; Inert atmosphere;

DOI:10.1021/jacs.1c06572

Reference yield: 80.0%

2-(1-oxo-1,3-dihydro-isoindol-2-yl)-pentanedioic acid anhydride (26581-82-8) → 3-(1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione (26581-81-7,103794-93-0,107740-48-7,107657-57-8)

Guidance literature:

With urea; at 180 ℃;

upstream raw materials:

2-(1-oxo-1,3-dihydro-isoindol-2-yl)-pentanedioic acid anhydride

1-(4-methoxybenzyl)-3-(1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

3-(1-hydroxy-3-oxoisoindolin-2-yl)piperidine-2,6-dione

thalidomide