31883-79-1

Basic information

• Product Name: 3-METHYL-3,4-DIHYDRO-1H-QUINOLIN-2-ONE
• Synonyms: 3-METHYL-3,4-DIHYDRO-1H-QUINOLIN-2-ONE;3-METHYL-3,4-DIHYDROQUINOLIN-2(1H)-ONE
• CAS NO: 31883-79-1
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.2
• Mol File: 31883-79-1.mol

Chemical Properties

• Melting Point: 130 °C
• Boiling Point: 325.1±31.0 °C(Predicted)
• Appearance: /
• Density: 1.083±0.06 g/cm3(Predicted)
• PKA: 14.80±0.40(Predicted)
• CAS DataBase Reference: 3-METHYL-3,4-DIHYDRO-1H-QUINOLIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-3,4-DIHYDRO-1H-QUINOLIN-2-ONE(31883-79-1)
• EPA Substance Registry System: 3-METHYL-3,4-DIHYDRO-1H-QUINOLIN-2-ONE(31883-79-1)

Safety Data

• Hazardous Substances Data: 31883-79-1(Hazardous Substances Data)

Upstream product

• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 74-88-4 methyl iodide 
• 94527-29-4 o-nitrobenzylidene du propionate d'ethyle 
• 159763-36-7 3-hydroxy-2-methylene-3-(2-nitrophenyl)propanoic acid methyl ester 
• 615-43-0 2-iodophenylamine 
• 80-62-6 methacrylic acid methyl ester 
• 365-33-3 2-nitrobenzenediazonium tetrafluoroborate 
• 201230-82-2 carbon monoxide 
• 32704-22-6 2-allyl-phenylamine 
• 577-19-5 2-nitrophenyl bromide 
• 60031-27-8 methyl 2-(2-nitrobenzyl)propanoate 
• 17496-14-9 2,3-dihydro-2-methyl-1H-inden-1-one 
• 1611-83-2 2-methyl-N-phenylacrylamide 
• 589-09-3 N-allyl-N-phenylamine 

Downstream Products

• 113092-96-9 6-bromo-2-chloro-3-methylquinoline 
• 2721-59-7 3-methylcarbostyril 
• 57876-69-4 2-chloro-3-methyl-quinoline 
• 113093-17-7 3-Chloro-3-methyl-3,4-dihydro-1H-quinolin-2-one 
• 92367-59-4 3,3-dimethyl-3,4-dihydroquinolin-2(1H)-one 

Relevant articles and documents

Evaluating thiourea/urea catalyst for enantioselective 6π-photocyclization of acrylanilides

6π-Photocyclization of acrylanilide with thiourea and urea based organocatalysts were evaluated to develop H-bonding activated photochemical reactions. These photochemical reactions resulted in a 3,4-dihydroquinolin-2-one photoproduct with low enantioselectivity. Photophysical studies revealed catalyst-substrate interactions in the excited state. The low chiral induction is likely due to a combination of low stereodifferentiation with respect to the mode of cyclization of the substrate by the catalyst, formation of an enol intermediate that destroys the chirality and the relative reactivity of the zwitterionic intermediate that competes with enol formation and direct hydrogen atom migration.

Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products

Oximes are valuable synthetic intermediates for the preparation of a variety of functional groups. To date, the stereoselective synthesis of oximes remains a major challenge, as most current synthetic methods either provide mixtures of E and Z isomers or furnish the thermodynamically preferred E isomer. Herein we report a mild and general method to achieve Z isomers of aryl oximes by photoisomerization of oximes via visible-light-mediated energy transfer (EnT) catalysis. Facile access to (Z)-oximes provides opportunities to achieve regio- and chemoselectivity complementary to those of widely used transformations employing oxime starting materials. We show an enhanced one-pot protocol for photocatalyzed oxime isomerization and subsequent Beckmann rearrangement that enables novel reactivity with alkyl groups migrating preferentially over aryl groups, reversing the regioselectivity of the traditional Beckmann reaction. Chemodivergent N- or O- cyclizations of alkenyl oximes are also demonstrated, leading to nitrones or cyclic oxime ethers, respectively.

HETEROCYCLIC COMPOUNDS AND USES THEREOF

Provided herein are novel heterocyclic compounds, for example, compounds having Formula I, I-P, II, lI-P, or III. Also provided herein are pharmaceutical compositions comprising the compounds and methods of using the same, for example, in inhibiting aldehyde dehydrogenases and/or for treating various cancers, cancer metastasis, type 2 diabetes, pulmonary arterial hypertension (PAH) or neointimal hyperplasia (NIH).

FUSED IMIDAZOLE AND PYRAZOLE DERIVATIVES AS MODULATORS OF TNF ACTIVITY

A series of substituted benzimidazole, imidazo[1,2-a]pyridine and pyrazolo[1,5-a]pyridine derivatives, and analogues thereof, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

Regiodivergent access to five- and six-membered benzo-fused lactams: Ru-catalyzed olefin hydrocarbamoylation

We report herein a new strategy of the Ru-catalyzed intramolecular olefin hydrocarbamoylation for the regiodivergent synthesis of five- and six-membered benzo-fused lactams starting from N-(2-alkenylphenyl)formamides. Using a combined catalyst of Ru3

Palladium-catalyzed β-arylation of silyl ketene acetals and application to the synthesis of benzo-fused δ-lactones

Silyl ketene acetals are shown to be competent nucleophiles in Pd-catalyzed migrative C(sp3)-H arylations. Compared to the parent ester lithium enolates, they possess decreased reactivity but enhanced chemoselectivity. This behavior was exploited through the synthesis of valuable benzo-fused δ-lactones such as 1-isochromanones and dihydrocoumarins.

Multicomponent multicatalyst reactions (MC)2R: One-pot synthesis of 3,4-dihydroquinolinones

A Rh/Pd/Cu catalyst system led to an efficient synthesis of dihydroquinolinones in one-pot, two operations. The reaction features the first triple metal-catalyzed transformations in one reaction vessel, without any intermediate workup. The conjugate-addition/amidation/amidation reaction sequence is highly modular, divergent, and practical.

Ionic diamine rhodium complex catalyzed hydroaminomethylation of 2-allylanilines

Ionic diamine rhodium complexes catalyze the hydroaminomethylation of 2-allylanilines. The reaction involves initial hydroformylation followed by reductive amination, which provides direct access to 1,2,3,4- tetrahydroquinolines and 2,3,4,5-1H-1-benzazepi

Preparation of 2-Quinolones by sequential heck reduction-cyclization (HRC) reactions by using a multitask palladium catalyst

One-pot sequential Heck reduction-cyclization (HRC) reactions leading to the synthesis of substituted 2-quinolones have been developed by using a heterogeneous or mixed homogeneous/heterogeneous multitask palladium catalyst with charcoal as a support. The whole sequence occurs under very mild conditions without the need for additives (ligand or base) by taking advantage of the high reactivity of aryldiazonium salts as "super electrophiles". Recycling experiments showed that the reused heterogeneous Pd°/C catalyst was not able to promote another HRC sequence but was, however, still highly active for hydrogenation, hydrodehalogenation, as well as hydrogenolysis reactions.

Convergent synthesis of dihydroquinolones from o-aminoarylboronates

An efficient and convergent one-step synthesis of substituted dihydroquinolin-2-ones from α,β-unsaturated esters and aminoaryl pinacolboronates under rhodium catalysis is reported. The reaction is easily applicable in parallel synthesis format and provide