103794-93-0

Basic information

• Product Name: 3-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione
• Synonyms: 2,6-piperidinedione, 3-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-
• CAS NO: 103794-93-0
• Molecular Formula: C₁₃H₁₂N₂O₃
• Molecular Weight: 244.246
• Mol File: 103794-93-0.mol

Chemical Properties

• Boiling Point: 534.3°C at 760 mmHg
• Flash Point: 276.9°C
• Density: 1.393g/cm³
• Vapor Pressure: 1.72E-11mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: 3-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione(103794-93-0)
• EPA Substance Registry System: 3-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione(103794-93-0)

Safety Data

• Hazardous Substances Data: 103794-93-0(Hazardous Substances Data)

Upstream product

• 26581-82-8 2-(1-oxo-1,3-dihydro-isoindol-2-yl)-pentanedioic acid anhydride 
• 222713-10-2 1-(4-methoxybenzyl)-3-(1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione 
• 58585-25-4 3-(1-hydroxy-3-oxoisoindolin-2-yl)piperidine-2,6-dione 
• 50-35-1 thalidomide 
• 222713-08-8 3-(1-hydroxy-3-oxo-1,3-dihydro-isoindol-2-yl)-1-(4-methoxy-benzyl)-piperidine-2,6-dione 
• 222713-07-7 2-[1-(4-methoxybenzyl)-2,6-dioxopiperidin-3-yl]isoindoline-1,3-dione 
• 222713-09-9 1-(4-methoxy-benzyl)-3-(1-oxo-3-phenylsulfanyl-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione 
• 6349-98-0 N-phthalylglutamic acid 
• 3343-28-0 N-phthaloylglutamic acid anhydride 
• 2417-73-4 methyl 2-bromomethylbenzoate 
• 2353-44-8 (+/-)-α-aminoglutarimide 
• 31140-42-8 (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester 
• 85535-45-1 5-amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid 
• 643-79-8 o-phthalic dicarboxaldehyde 

Relevant articles and documents

COMPOUNDS MODULATING PROTEIN RECRUITMENT AND/OR DEGRADATION

The invention provides cereblon binders for the degradation of proteins by the ubiquitin proteasome pathway for therapeutic applications.

Chemoselective Electrosynthesis Using Rapid Alternating Polarity

Challenges in the selective manipulation of functional groups (chemoselectivity) in organic synthesis have historically been overcome either by using reagents/catalysts that tunably interact with a substrate or through modification to shield undesired sites of reactivity (protecting groups). Although electrochemistry offers precise redox control to achieve unique chemoselectivity, this approach often becomes challenging in the presence of multiple redox-active functionalities. Historically, electrosynthesis has been performed almost solely by using direct current (DC). In contrast, applying alternating current (AC) has been known to change reaction outcomes considerably on an analytical scale but has rarely been strategically exploited for use in complex preparative organic synthesis. Here we show how a square waveform employed to deliver electric current - rapid alternating polarity (rAP) - enables control over reaction outcomes in the chemoselective reduction of carbonyl compounds, one of the most widely used reaction manifolds. The reactivity observed cannot be recapitulated using DC electrolysis or chemical reagents. The synthetic value brought by this new method for controlling chemoselectivity is vividly demonstrated in the context of classical reactivity problems such as chiral auxiliary removal and cutting-edge medicinal chemistry topics such as the synthesis of PROTACs.

THALIDOMIDE ANALOGS AND METHODS OF USE

Thalidomide analogs and methods of using the thalidomide analogs are disclosed. Some embodiments of the disclosed compounds exhibit anti- angiogenic and/or anti-inflammatory activity. Certain embodiments of the disclosed compounds are non-teratogenic.

Thalidomide metabolites and analogues. 3. Synthesis and antiangiogenic activity of the teratogenic and TNFα-modulatory thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine

Versatile synthesis of the teratogenic, TNFα-modulatory, and antiangiogenic thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine (1) and its direct antiangiogenic properties are described. With thalidomide or thalidomide derivatives as precursors, the synthesis involved either carbonyl reduction/thiation-desulfurization or carbonyl reduction/acyliminium ion reduction protocols. Compared to earlier studies with thalidomide, which was only active with microsomal treatment, 1 exhibited marginal inhibitory activity in the rat aortic ring assay, thereby demonstrating the requirement for metabolic activation.

A facile scheme for phthalimide ? phthalimidine conversion

Desulfurization of phenylthiolactams using an ultrasound-promoted Raney nickel protocol yields the corresponding N-substituted phthalimidines. Benzylic oxidation of the N-substituted phthalimidines by treatment with 2,2'-bipyridinium chlorochromate/m-chloroperbenzoic acid (BPCC/MCPBA) affords the original phthalimides. The reduction-desulfurization is applied to the preparation of a deoxythalidomide derivative which is a TNF-α inhibitor.

Comparative teratological investigation of compounds structurally and pharmacologically related to thalidomide

Compounds differing from thalidomide in either the phthalimide or the 2,6-dioxopiperidine moiety of the molecule were synthetized and tested for teratogenic potency in White New Zealand rabbits. Both the 2,6-dioxopiperidine and 2-oxopiperidine derivatives of phthalimide and phthalimidine were found to be highly teratogenic. A somewhat higher teratogenic potential appeared to be associated with the 2,6-dioxopiperidine derivatives. The most potent teratogen investigated was clearly 3-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-dioxopiperidine (EM 12). Compounds in which the phthalimide ring was replaced by 2,3-dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol, did not induce any embryopathic effect differing from control data. No consistent correlation between teratogenic activity and sedative properties of the compounds was detected. The results are discussed in respect to current views of the molecular mechanism leading to thalidomide embryopathy.