13268-54-7

Basic information

• Product Name: 1,2-Dihydro-1-tosylquinoline
• Synonyms: 1,2-Dihydro-1-(p-tolylsulfonyl)quinoline;1,2-Dihydro-1-tosylquinoline
• CAS NO: 13268-54-7
• Molecular Formula: C₁₆H₁₅NO₂S
• Molecular Weight: 285.3608
• Mol File: 13268-54-7.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 442.9°Cat760mmHg
• Flash Point: 221.7°C
• Appearance: /
• Density: 1.273g/cm³
• Vapor Pressure: 4.84E-08mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: 1,2-Dihydro-1-tosylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dihydro-1-tosylquinoline(13268-54-7)
• EPA Substance Registry System: 1,2-Dihydro-1-tosylquinoline(13268-54-7)

Safety Data

• Hazardous Substances Data: 13268-54-7(Hazardous Substances Data)

Usage

General Description

1,2-Dihydro-1-tosylquinoline, also known as 1-tosyl-1,2,3,4-tetrahydroquinoline, is a chemical compound with the molecular formula C16H17NO2S. It is a tosylated derivative of tetrahydroquinoline, and it is commonly used as a building block in organic synthesis. 1,2-Dihydro-1-tosylquinoline is a white to off-white solid that is sparingly soluble in water, but soluble in organic solvents such as acetone and ethyl acetate. 1,2-Dihydro-1-tosylquinoline is commonly used as a reagent in various chemical reactions, particularly in the synthesis of pharmaceuticals and other organic compounds. It is an important intermediate in the production of various organic compounds and is utilized in research and development in the field of organic chemistry.

InChI:InChI=1/C16H15NO2S/c1-13-8-10-15(11-9-13)20(18,19)17-12-4-6-14-5-2-3-7-16(14)17/h2-11H,12H2,1H3

Upstream product

• 1038502-78-1 6-methyl-1-tosyl-4-vinyl-1H-benzo[d][1,3]oxazin-2(4H)-one 
• 15119-34-3 3-cyanocoumarin 
• 1038502-72-5 1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one 
• 1038502-69-0 (7E,15E)-5,13-ditosyl-5,6,13,14-tetrahydrodibenzo[b,h][1,7]diazacyclododecine 
• 91-22-5 quinoline 
• 14278-37-6 1-tosyl-2,3-dihydroquinolin-4(1H)-one 
• 68-34-8 phenyl toluenesulfonamide 
• 30765-95-8 N-p-toluenesulfonyl-2-vinylaniline 
• 497066-36-1 N-allyl-4-methyl-N-(2-vinyl-phenyl)-benzenesulfonamide 
• 333383-70-3 4-methyl-N-(3-oxo-propyl)-N-phenyl-benzenesulfonamide 
• 51315-69-6 N-tosyl-o-allylaniline 
• 24206-42-6 1,2,3,4-tetrahydro-4-hydroxy-1-tosylquinoline 
• 612-18-0 1,2-dihydroquinoline 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1666-96-2 3-phenylquinoline 
• 159682-32-3 1,2,3,4-tetrahydro-3-(2'-hydroxyphenyl)quinoline 
• 91-22-5 quinoline 
• 159682-30-1 7,12-dihydro-7-tosyl-6,12-methano-2,3-methylenedioxy-6H-dibenzo<1,3>oxazocine 

Relevant articles and documents

Access to benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety: Via a double decarboxylative formal ring-expansion process under palladium catalysis

Direct access to pharmaceutically attractive benzo-fused nine-membered heterocyclic alkenes 3 with a trifluoromethyl carbinol moiety was achieved via a palladium-catalyzed double-decarboxylative formal ring-expansion process from six-membered trifluoromethyl benzo[d][1,3]oxazinones 1 to nine-membered trifluoromethyl benzo[c][1,5]oxazonines 3 in the presence of vinylethylene carbonates 2. Generation of a Pd-π-allyl zwitterionic intermediate was proposed in the catalytic cycle. The trifluoromethyl group in the benzoxazinanones 1 plays an important role throughout the transformation. Diastereoselective chemical transformations of products 3 were also demonstrated.

Hydrogen Bonding Networks Enable Br?nsted Acid-Catalyzed Carbonyl-Olefin Metathesis**

Synthetic chemists have learned to mimic nature in using hydrogen bonds and other weak interactions to dictate the spatial arrangement of reaction substrates and to stabilize transition states to enable highly efficient and selective reactions. The activation of a catalyst molecule itself by hydrogen-bonding networks, in order to enhance its catalytic activity to achieve a desired reaction outcome, is less explored in organic synthesis, despite being a commonly found phenomenon in nature. Herein, we show our investigation into this underexplored area by studying the promotion of carbonyl-olefin metathesis reactions by hydrogen-bonding-assisted Br?nsted acid catalysis, using hexafluoroisopropanol (HFIP) solvent in combination with para-toluenesulfonic acid (pTSA). Our experimental and computational mechanistic studies reveal not only an interesting role of HFIP solvent in assisting pTSA Br?nsted acid catalyst, but also insightful knowledge about the current limitations of the carbonyl-olefin metathesis reaction.

Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis

The synthesis of 1,2-dihydroquinolines by the hydrazine-catalyzed ring-closing carbonyl-olefin metathesis (RCCOM) of N-prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of substitution patterns are shown. With an acid-labile protecting group on the nitrogen atom, in situ deprotection and autoxidation furnish quinoline. In comparison with related oxygen-containing substrates, the cycloaddition step of the catalytic cycle is shown to be slower, but the cycloreversion is found to be more facile.