260412-75-7

Basic information

• Product Name: t-Butyl 1,3-dihydroisoindole-2-carboxylate
• Synonyms: t-Butyl 1,3-dihydroisoindole-2-carboxylate;1,3-Dihydro-isoindole-2-carboxylic acid tert-butyl ester;tert-Butyl isoindoline-2-carboxylate;2H-Isoindole-2-carboxylic acid, 1,3-dihydro-, 1,1-dimethylethyl ester
• CAS NO: 260412-75-7
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.27958
• Mol File: 260412-75-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: t-Butyl 1,3-dihydroisoindole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: t-Butyl 1,3-dihydroisoindole-2-carboxylate(260412-75-7)
• EPA Substance Registry System: t-Butyl 1,3-dihydroisoindole-2-carboxylate(260412-75-7)

Safety Data

• Hazardous Substances Data: 260412-75-7(Hazardous Substances Data)

Usage

General Description

t-Butyl 1,3-dihydroisoindole-2-carboxylate is a compound that belongs to the class of organic chemicals known as benzodihydroisoquinolines and related structures. It is a t-butyl ester derivative of 1,3-dihydroisoindole-2-carboxylic acid, and its chemical formula is C14H19NO2. This chemical is commonly used in the pharmaceutical industry as a building block for the synthesis of various drugs and bioactive molecules. It has also been studied for its potential pharmacological properties, including its ability to inhibit certain enzymes and receptors in the body. Additionally, it has been investigated for its potential applications in organic synthesis and material science.

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 articles and documents

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.

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.