179898-00-1

Basic information

• Product Name: TERT-BUTYL 4-OXO-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE
• Synonyms: TERT-BUTYL 4-OXO-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE;N-Boc-3,4-dihydroquinoline-4(2H)-one;4-Oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester
• CAS NO: 179898-00-1
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.3
• Mol File: 179898-00-1.mol

Chemical Properties

• Boiling Point: 360.706°C at 760 mmHg
• Flash Point: 171.949°C
• Appearance: /
• Density: 1.172g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: 2-8°C
• PKA: -1.91±0.20(Predicted)
• CAS DataBase Reference: TERT-BUTYL 4-OXO-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 4-OXO-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE(179898-00-1)
• EPA Substance Registry System: TERT-BUTYL 4-OXO-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE(179898-00-1)

Safety Data

• Hazardous Substances Data: 179898-00-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
TERT-BUTYL 4-OXO-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE is used as an intermediate in the synthesis of pharmaceuticals for its potential to contribute to the development of new drugs. Its unique structure allows it to be a key component in creating molecules with therapeutic properties.
Used in Agrochemical Synthesis:
In the agrochemical industry, TERT-BUTYL 4-OXO-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE is used as a precursor in the development of agrochemicals, such as pesticides and herbicides, due to its ability to be incorporated into molecules that can target and control various agricultural pests and weeds.
Used in Medicinal Chemistry Research:
TERT-BUTYL 4-OXO-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE is utilized as a subject of research in medicinal chemistry to explore its potential therapeutic applications. Its pharmacological properties are of interest to scientists who aim to understand and harness its capabilities for treating various diseases and conditions.
Used in Biological Activity Studies:
TERT-BUTYL 4-OXO-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE is also used in biological activity studies to investigate its interactions with biological systems. Understanding these interactions can lead to insights into how it may be used to modulate biological processes for therapeutic benefit.

InChI:InChI=1/C14H17NO3/c1-14(2,3)18-13(17)15-9-8-12(16)10-6-4-5-7-11(10)15/h4-7H,8-9H2,1-3H3

Upstream product

• 4295-36-7 2,3-dihydroquinolin-4(1H)-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 123387-53-1 tert-butyl 1,2,3,4-tetrahydroquinoline-1-carboxylate 
• 5652-38-0 N-phenyl-β-alanine 
• 62-53-3 aniline 
• 179898-22-7 7-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline 
• 1407968-48-2 3-[N-(tert-butoxycarbonyl)-N-(2-iodophenyl)amino]propanal 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 7661-07-6 3-bromo-N-phenylpropanamide 
• 5099-95-6 1-phenylazetidin-2-one 

Downstream Products

• 19343-78-3 4-methyl-1,2,3,4-tetrahydroquinoline 
• 17507-29-8 4-(2-methylpropyl)-1,2,3,4-tetrahydroquinoline 
• 1146210-98-1 C₂₁H₂₁F₂N₃O₃ 
• 1535200-77-1 (E)-tert-butyl 4-benzylidene-3,4-dihydroquinoline-1(2H)-carboxylate 
• 1535200-81-7 (Z)-tert-butyl 4-benzylidene-3,4-dihydroquinoline-1(2H)-carboxylate 
• 4295-36-7 2,3-dihydroquinolin-4(1H)-one 

Relevant articles and documents

Manganese-Catalyzed Asymmetric Oxidation of Methylene C-H of Spirocyclic Oxindoles and Dihydroquinolinones with Hydrogen Peroxide

A highly efficient strategy for the enantioselective oxidation of methylene C-H of spirocyclic oxindoles and dihydroquinolinones has been established, in which an earth-abundant manganese catalyst and hydrogen peroxide are used. Noteworthy, the manganese catalyst can be applied to the asymmetric hydroxylation of spirocyclic 2,3-dihydroquinolin-4-ones with 94-99% ee.

INHIBITORS OF NOROVIRUS AND CORONAVIRUS REPLICATION

Compounds of Formula (I) and methods of inhibiting the replication of viruses in a biological sample or patient, of reducing the amount of viruses in a biological sample or patient, and of treating a virus infection in a patient, comprising administering to said biological sample or patient an effective amount of a compound represented by Formula (I), a compound of Table A or B or a pharmaceutically acceptable salt thereof.

Multi-Functional Oxidase Activity of CYP102A1 (P450BM3) in the Oxidation of Quinolines and Tetrahydroquinolines

Tetrahydroquinoline, quinoline, and dihydroquinolinone are common core motifs in drug molecules. Screening of a 48-variant library of the cytochrome P450 enzyme CYP102A1 (P450BM3), followed by targeted mutagenesis based on mutation-selectivity correlations from initial hits, has enabled the hydroxylation of substituted tetrahydroquinolines, quinolines, and 3,4-dihydro-2-quinolinones at most positions around the two rings in good to high yields at synthetically relevant scales (1.5 g L?1 day?1). Other oxidase activities, such as C?C bond desaturation, aromatization, and C?C bond formation, were also observed. The enzyme variants, with mutations at the key active site residues S72, A82, F87, I263, E267, A328, and A330, provide direct and sustainable routes to oxy-functionalized derivatives of these building block molecules for synthesis and drug discovery.

Asymmetric Synthesis of Cyclopentene-Fused Tetrahydroquinolines via N-Heterocyclic Carbene Catalyzed Domino Reactions

A new strategy for the N-heterocyclic carbene catalyzed asymmetric synthesis of cyclopentene-fused tetrahydroquinoline derivatives has been developed. The one-pot organocatalytic domino protocol allows a direct entry to the characteristic cyclopenta[ c ]tetrahydroquinoline core of many alkaloids and some potential drugs employing readily available quinolinone and enal substrates in good domino yields and stereoselectivities.

DUAL NAV1.2/5HT2A INHIBITORS FOR TREATING CNS DISORDERS

Compounds of formula I: I are disclosed, as are pharmaceutical compositions containing such compounds. Methods of treating neurological or psychiatric disorders in a patient in need are also disclosed. Such disorders include depression, bipolar disorder, pain, schizophrenia, obsessive compulsive disorder, addiction, social disorder, attention deficit hyperactivity disorder, an anxiety disorder, autism, a cognitive impairment, or a neuropsychiatric symptom such as apathy, depression, anxiety, psychosis, aggression, agitation, impulse control disorders, and sleep disorders in neurological disorders such as Alzheimer's and Parkinson's diseases.

THERAPEUTIC COMPOUNDS AND USES THEREOF

Provided herein are compounds of formula I: and salts thereof and compositions and uses thereof. The compounds are useful as inhibitors of LSD1. Also included are pharmaceutical compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof, and methods of using such compounds and salts in the treatment of various LSD1-mediated disorders.

PIPERIDINE DERIVATIVES AS HDAC1/2 INHIBITORS

Provided herein are compounds, pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat diseases or disorders associated with HDACl and/or HDAC2 activity.

Novozyme 435 lipase mediated enantioselective kinetic resolution: A facile method for the synthesis of chiral tetrahydroquinolin-4-ol and tetrahydro-1H-benzo[b]azepin-5-ol derivatives

Vinyl 2-chloroacetate was used as an efficient acyl donor for enantioselective acylation of racemic 1,2,3,4-tetrahydroquinolin-4-ols and 2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ols with Novozyme 435 lipase. Two enantiocomplimentary tetrahydroquinolin-4-ol

Intramolecular Pd(0)-catalyzed reactions of (2-iodoanilino)-aldehydes: A joint experimental-computational study

An extensive joint experimental-computational density functional theory (DFT) study has been carried out to gain insight into the factors that control the chemoselectivity (i.e., acylation vs α-arylation reaction) of palladium-catalyzed cyclizations of (2-iodoanilino)-aldehydes. To this end, the nature of the tethers joining the aniline nitrogen and the aldehyde moiety, different palladium precatalysts and reaction conditions (base and temperature), as well as different additives (mono- and bidendate ligands) has been explored. The adequate selection of these variables allows for the control of the selectivity of the process. Thus, (2-iodoanilino)-aldehydes generally lead to the formation of nucleophilic addition derived products when Cs 2CO3/Et3N is used as base. In contrast, the use of stronger bases like KtOBu (in the presence of PhOH) mainly forms α-arylation reaction products. The different reaction pathways leading to the experimentally observed reaction products have been studied by means of computational tools.