55908-34-4

Basic information

• Product Name: A-METHYL-4-QUINOLINEMETHANOL
• Synonyms: 4-QUINOLINEMETHANOL, A-METHYL-;A-METHYL-4-QUINOLINEMETHANOL;4-Quinolinemethanol,α-methyl-;1-Quinolin-4-yl-ethanol
• CAS NO: 55908-34-4
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.214
• Mol File: 55908-34-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: A-METHYL-4-QUINOLINEMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: A-METHYL-4-QUINOLINEMETHANOL(55908-34-4)
• EPA Substance Registry System: A-METHYL-4-QUINOLINEMETHANOL(55908-34-4)

Safety Data

• Hazardous Substances Data: 55908-34-4(Hazardous Substances Data)

Upstream product

• 4363-93-3 quinoline-4-carboxaldehyde 
• 75-16-1 methylmagnesium bromide 
• 74-88-4 methyl iodide 
• 19020-26-9 4-ethylquinoline 
• 917-64-6 methyl magnesium iodide 
• 91-22-5 quinoline 
• 64-17-5 ethanol 

Downstream Products

• 4945-29-3 4-vinylquinoline 
• 19020-26-9 4-ethylquinoline 
• 60814-30-4 4-acetylquinoline 
• 161906-99-6 (R)-4-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-trimethylsilanylethynyl-2H-quinoline-1-carboxylic acid phenyl ester 
• 161824-79-9 (1aS,2S,7bR)-7b-Acetyl-2-((Z)-6-trimethylsilanyl-hex-3-ene-1,5-diynyl)-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester 
• 161824-78-8 (1aS,2S,7bR)-7b-Acetyl-2-ethynyl-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester 
• 169103-36-0 (1aS,2S,7bS)-2-Ethynyl-7b-((S)-1-hydroxy-ethyl)-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester 
• 161906-98-5 4-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-quinoline 
• 161824-77-7 (R)-2-Ethynyl-4-((S)-1-hydroxy-ethyl)-2H-quinoline-1-carboxylic acid phenyl ester 
• 168843-97-8 4-[1-(4-Methoxy-benzyloxy)-ethyl]-quinoline 

Relevant articles and documents

Synthetic studies on antibiotic dynemicin A. Synthesis of cyclic enediyne model compound of dynemicin A

Dynemicin A, a potent antitumor antibiotic has novel 10-membered cyclic enediyne moiety. The bicyclo[7.3.1]-tridecadiyne system having aniline moiety of this antibiotic was designed and synthesized from lepidine in 10 steps. The synthesized compound can be cycloaromatized to Bergman product via pinacol rearrangement under acidic condition, and also exhibited DNA cleaving activity.

Metal-Free Chemoselective Oxidation of 4-Methylquinolines into Quinoline-4-Carbaldehydes

A convenient protocol for the synthesis of quinoline-4-carbaldehydes via chemoselective oxidation of 4-methylquinolines using hypervalent iodine(III) reagents as oxidant is described. This method highlights metal-free and mild reaction conditions, nice yield, good functional group tolerance, and high chemoselectivity.

METHOD OF PREPARING SILYLATIVE-REDUCED N-HETEROCYCLIC COMPOUND USING ORGANOBORON CATALYST

Provided is a method of preparing a silylative-reduced N-heterocyclic compound by reducing an N-heteraromatic compound including a sp2 hybridized nitrogen atom while simultaneously introducing a silyl group into a beta-position with respect to a nitrogen atom of the N-heteroaromatic compound, using a silane compound, in the presence of an organoboron catalyst.

Boron-catalyzed silylative reduction of quinolines: Selective sp3 C-Si bond formation

A silylative reduction of quinolines to synthetically versatile tetrahydroquinoline molecules involving the formation of a C(sp3)-Si bond exclusively β to nitrogen is described. Triarylborane is a highly efficient catalyst (up to 1000 turnovers), and silanes serve as both a silyl source and a reducing reagent. The present procedure is convenient to perform even on a large scale with excellent stereoselectivity. Mechanistic studies revealed that the formation of a 1,4-addition adduct is rate-limiting while the subsequent C(sp3)-Si bond-forming step from the 1,4-adduct is facile.

Palladium-catalyzed Minisci reaction with simple alcohols

A palladium-catalyzed coupling of N-heterocycles with simple alcohols was achieved. The reaction is initiated by peroxide and does not require the use of stoichiometric acid for activation of the heterocycle.

NOVEL CYCLIC COMPOUND HAVING QUINOLYLALKYLTHIO GROUP

The present invention relates to a synthesis study of novel cyclic compounds having a quinolylalkylthio group represented by the formula (1), and pharmacological actions of the compounds. In the formula, the ring X represents: which may have halogen and/or alkyl; R1 and R2 independently represent hydrogen, alkyl, cycloalkyl, aryl or a (non) aromatic heterocycle; R3 represents qinolyl; A represents sulfur, sulfinyl or sulfonyl; and B represents alkylene.

CALCIUM RECEPTOR MODULATING ARYLALKYLAMINES

The compounds of the invention are represented by the following general structure (I) or a pharmaceutically acceptable salt thereof, and compositions containing them, wherein the variables are defined herein, and their use to reduce or inhibit PTH secretion, including methods for reducing or inhibiting PTH secretion and methods for treatment or prophylaxis of diseases associated with bone disorders, such as osteoporosis, or associated with excessive secretion of PTH, such as hyperparathyroidism. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

Imidazole and imidazoline derivatives and uses thereof

This invention is directed to novel imidazole and imidazoline derivatives which are selective agonists for cloned human α2 adrenergic receptors. This invention is also related to the use of these compounds for the treatment of any disease where

Synthesis of a Simple Model Compound of Dynemicin and Cycloaromatization with Pinacol-Pinacolone Rearrangement in the Strained Enediyne Medium Ring

Novel bicyclo-tridecdiyne system included in dynemicin was synthesized from a quinoline aldehyde in 9 steps.Key step was the cyclization with silyl acetylene to ketone carbonyl group through fluoride activation with CsF.The cyclized compound did aromatize under acidic condition, with opening of the epoxide ring, to give a Bergman product that was further converted with pinacol-pinacolone rearrangement.

Synthesis of 4-Vinylquinoline: Pyrolytic Rearrangement of the 4-(1-Hydroxyethyl)quinoline and Related Derivatives

The synthesis of 4-vinylquinoline has been carried out by means of the Wittig reaction between 4-quinolinecarbaldehyde and the methyl triphenylphosphonium ylide in dimethyl sulphoxide in good yield.Dehydration of the 4-(1-hydroxyethyl)quinoline and their xanthate derivative, give equimolar amounts of 4-ethylquinoline and 4-acetylquinoline while small amounts of 4-vinylquinoline were found.Dehydrochlorination of 4-(1-chloroethyl)quinoline in ethanol-sodium hydroxide provides 4-ethyl-3-ethoxyquinoline in good yield, but 4-vinylquinoline is a minor reaction product.