260412-75-7

Usage

Uses

Used in Pharmaceutical Industry:
t-Butyl 1,3-dihydroisoindole-2-carboxylate is used as a building block for the synthesis of various drugs and bioactive molecules. Its unique structure and functional groups make it a valuable component in the development of new pharmaceutical agents.
Used in Organic Synthesis:
t-Butyl 1,3-dihydroisoindole-2-carboxylate is used as a key intermediate in the synthesis of complex organic compounds. Its reactivity and stability contribute to the formation of a wide range of chemical products.
Used in Material Science:
t-Butyl 1,3-dihydroisoindole-2-carboxylate is used in the development of new materials with specific properties. Its incorporation into polymers and other materials can enhance their performance and create novel applications.
Used in Enzyme and Receptor Inhibition:
t-Butyl 1,3-dihydroisoindole-2-carboxylate has been studied for its potential pharmacological properties, including its ability to inhibit certain enzymes and receptors in the body. This makes it a candidate for the development of drugs targeting specific biological pathways.

Upstream product

• 496-12-8 isoindoline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 126799-83-5 2-methylbenzylazide 

Downstream Products

• 1620-30-0 diphenyl(pyridin-4-yl)methanol 

Relevant academic research and scientific papers

Generation and Alkylation of α-Carbamyl Radicals via Organic Photoredox Catalysis

Strategies for the direct C-H functionalization of amines are valuable as these compounds comprise a number of pharmaceuticals, agrochemicals and natural products. This work describes a novel method for the C-H functionalization of carbamate-protected secondary amines via α-carbamyl radicals generated using photoredox catalysis. The use of the highly oxidizing, organic acridinium photoredox catalyst allows for direct oxidation of carbamate-protected amines with high redox potentials to give the corresponding carbamyl cation radical. Following deprotonation, the resultant open-shell species can be intercepted by a variety of Michael acceptors to give elaborate α-functionalized secondary amines. The reaction proceeds under mild conditions without the requirement of exogenous redox mediators or substrate prefunctionalization. Additionally, we were able to showcase the utility of this methodology through the enantioselective synthesis of the indolizidine alkaloid, (+)-monomorine I.

Cobalt-Porphyrin-Catalysed Intramolecular Ring-Closing C?H Amination of Aliphatic Azides: A Nitrene-Radical Approach to Saturated Heterocycles

Cobalt-porphyrin-catalysed intramolecular ring-closing C?H bond amination enables direct synthesis of various N-heterocycles from aliphatic azides. Pyrrolidines, oxazolidines, imidazolidines, isoindolines and tetrahydroisoquinoline can be obtained in good to excellent yields in a single reaction step with an air- and moisture-stable catalyst. Kinetic studies of the reaction in combination with DFT calculations reveal a metallo-radical-type mechanism involving rate-limiting azide activation to form the key cobalt(III)-nitrene radical intermediate. A subsequent low barrier intramolecular hydrogen-atom transfer from a benzylic C?H bond to the nitrene-radical intermediate followed by a radical rebound step leads to formation of the desired N-heterocyclic ring products. Kinetic isotope competition experiments are in agreement with a radical-type C?H bond-activation step (intramolecular KIE=7), which occurs after the rate-limiting azide activation step. The use of di-tert-butyldicarbonate (Boc2O) significantly enhances the reaction rate by preventing competitive binding of the formed amine product. Under these conditions, the reaction shows clean first-order kinetics in both the [catalyst] and the [azide substrate], and is zero-order in [Boc2O]. Modest enantioselectivities (29–46 % ee in the temperature range of 100–80 °C) could be achieved in the ring closure of (4-azidobutyl)benzene using a new chiral cobalt-porphyrin catalyst equipped with four (1S)-(?)-camphanic-ester groups.

Catalytic Synthesis of N-Heterocycles via Direct C(sp3)-H Amination Using an Air-Stable Iron(III) Species with a Redox-Active Ligand

Coordination of FeCl3 to the redox-active pyridine-aminophenol ligand NNOH2 in the presence of base and under aerobic conditions generates FeCl2(NNOISQ) (1), featuring high-spin FeIII and an NNOISQ radical ligand. The complex has an overall S = 2 spin state, as deduced from experimental and computational data. The ligand-centered radical couples antiferromagnetically with the Fe center. Readily available, well-defined, and air-stable 1 catalyzes the challenging intramolecular direct C(sp3)-H amination of unactivated organic azides to generate a range of saturated N-heterocycles with the highest turnover number (TON) (1 mol% of 1, 12 h, TON = 62; 0.1 mol% of 1, 7 days, TON = 620) reported to date. The catalyst is easily recycled without noticeable loss of catalytic activity. A detailed kinetic study for C(sp3)-H amination of 1-azido-4-phenylbutane (S1) revealed zero order in the azide substrate and first order in both the catalyst and Boc2O. A cationic iron complex, generated from the neutral precatalyst upon reaction with Boc2O, is proposed as the catalytically active species.

Inhibitors of dipeptidyl peptidase 8 and dipeptidyl peptidase 9. Part 2: Isoindoline containing inhibitors

To obtain selective and potent inhibitors of dipeptidyl peptidases 8 and 9, we synthesized a series of substituted isoindolines as modified analogs of allo-Ile-isoindoline, the reference DPP8/9 inhibitor. The influence of phenyl substituents and different P2 residues on the inhibitors' affinity toward other DPPs and more specifically, their potential to discriminate between DPP8 and DPP9 will be discussed. Within this series compound 8j was shown to be a potent and selective inhibitor of DPP8/9 with low activity toward DPP II.