16808-41-6

Basic information

• Product Name: 2-(AdaMantan-1-yl)isoindoline-1,3-dione
• Synonyms: 2-(AdaMantan-1-yl)isoindoline-1,3-dione;2-(1-adamantyl)isoindole-1,3-dione;2-(1-adamantyl)isoindoline-1,3-dione;2-(1-adamantyl)isoindoline-1,3-quinone;AIDS089084;AIDS-089084;N-(1-Adamantyl)phthalimide;STK282264
• CAS NO: 16808-41-6
• Molecular Formula: C₁₈H₁₉NO₂
• Molecular Weight: 281.34896
• Mol File: 16808-41-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 137-138 °C
• Boiling Point: 414.3°Cat760mmHg
• Flash Point: 180.5°C
• Appearance: /
• Density: 1.336g/cm³
• Vapor Pressure: 4.5E-07mmHg at 25°C
• Refractive Index: 1.661
• PKA: -2.18±0.20(Predicted)
• CAS DataBase Reference: 2-(AdaMantan-1-yl)isoindoline-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(AdaMantan-1-yl)isoindoline-1,3-dione(16808-41-6)
• EPA Substance Registry System: 2-(AdaMantan-1-yl)isoindoline-1,3-dione(16808-41-6)

Safety Data

• Hazardous Substances Data: 16808-41-6(Hazardous Substances Data)

Usage

Molecular class

Isoindoline-1,3-dione compounds

Structural feature

Contains an adamantane group

Known for

Diverse range of pharmaceutical and biological activities

Importance in drug design

Adds steric and conformational properties

Potential for further research

Synthesis and potential applications in medicinal chemistry

InChI:InChI=1/C18H19NO2/c20-16-14-3-1-2-4-15(14)17(21)19(16)18-8-11-5-12(9-18)7-13(6-11)10-18/h1-4,11-13H,5-10H2

Upstream product

• 85-44-9 phthalic anhydride 
• 768-94-5 1-Adamantanamine 
• 768-95-6 1-adamanthanol 
• 136918-14-4 phthalimide 
• 612058-38-5 (1-adamantyloxy)di(phenyl)phosphine 
• 6221-58-5 bicyclo[3.3.1]nonane-3,7-dicarboxylic acid 
• 107-13-1 acrylonitrile 
• 1581695-79-5 2-cyanotricyclo[3.3.1.1^3,7]decane-1-carboxylic acid 
• 1064664-26-1 ethyl 2-cyanotricyclo[3.3.1.1^3,7]decane-1-carboxylate 
• 25995-06-6 ethyl 2-oxoadamantane-1-carboxylate 
• 24569-89-9 1,3-dehydroadamantane 
• 6240-10-4 3-amino-1-adamantanecarboxylic acid 
• 1333108-05-6 3-(N-phthalimido)-1-adamantane carboxylic acid 
• 292638-85-8 acrylic acid methyl ester 

Relevant articles and documents

Tumor necrosis factor-alpha production-regulating activity of phthalimide derivatives in genetically modified murine melanoma cells B78H1

The effect of imides, monothioimides, trimellitimides, as well as 5′-deoxy-5′-phthaloylamino-derivatives of azidothymidine on tumor necrosis factor-alpha (TNF-α) production by genetically modified murine B78H1 melanoma cells transduced with the gene for human TNF-α (B78/TNF) was investigated. It was found that N-(adamant-1-yl)monothiophthalimide (1e) and N-(adamant-2-yl)-monothiophthalimide (1f) showed over 200% enhancing of TNF-α production while some of imides were inhibitors.

Cyclic (Aryl)(Amido)Carbenes: NHCs with Triplet-like Reactivity

The synthesis and study of a library of cyclic (aryl)(amido)carbenes (CArAmCs), which represent a class of electrophilic NHCs that feature low calculated singlet-triplet gaps (ΔEST=19.9 kcal mol?1; B3LYP/def2-TZVP) and exhibit reactivity profiles expected from triplet carbenes, are described. The electrophilic properties of the CArAmCs were quantified by analyzing their respective selenium adducts, which exhibited the largest downfield 77Se NMR chemical shifts (up to 1645 ppm) measured for any NHC derivative known to date, as well as their Ir carbonyl complexes, from which large Tolman electronic parameter (TEP) values (up to 2064 cm?1) were ascertained. The CArAmCs were found to engage in reactions that are typically observed with triplet carbenes, including C?H insertions, [2+1] cycloadditions with alkenes as well as alkynes, and spontaneous oxidation upon exposure to oxygen.

Alkylphosphinites as Synthons for Stabilized Carbocations

We present a new acid-free method for the generation of carbocations based on a redox condensation reaction that enables SN1 reactions with a variety of nucleophiles. We utilize readily synthesized phosphinites that are activated by diisopropyl azodicarboxylate to form betaine structures that collapse upon adding a pronucleophile, thereby yielding reactive carbocation intermediates. We also employ this approach for the alkylation of some bioactive molecules.

NEW CRBN MODULATORS

Disclosed are degraders, pharmaceutical compositions containing them, and methods of making and using the degraders to treat diseases and disorders characterized by dysregulated or dysfunctional protein activity that can be targeted by cereblon.