291275-45-1

Basic information

• Product Name: (Z)-tert-butyl-[1-(3-chlorophenyl)prop-1-enyloxy]dimethylsilane
• Synonyms: (Z)-tert-butyl-[1-(3-chlorophenyl)prop-1-enyloxy]dimethylsilane
• CAS NO: 291275-45-1
• Molecular Weight: 282.886
• Mol File: 291275-45-1.mol

Chemical Properties

• CAS DataBase Reference: (Z)-tert-butyl-[1-(3-chlorophenyl)prop-1-enyloxy]dimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-tert-butyl-[1-(3-chlorophenyl)prop-1-enyloxy]dimethylsilane(291275-45-1)
• EPA Substance Registry System: (Z)-tert-butyl-[1-(3-chlorophenyl)prop-1-enyloxy]dimethylsilane(291275-45-1)

Safety Data

• Hazardous Substances Data: 291275-45-1(Hazardous Substances Data)

Upstream product

• 34841-35-5 3'-chloro-propiophenone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 587-04-2 m-Chlorobenzaldehyde 
• 1190391-42-4 tert-butyldimethyl(1-m-chlorophenyl-prop-2-en-1-yloxy)silane 

Downstream Products

• 287477-53-6 (S)-1-(3-chlorophenyl)-2-hydroxypropan-1-one 
• 291275-46-2 (R)-(+)-1-(3-chlorophenyl)-2-hydroxypropan-1-one 
• 192374-14-4 radafaxine 
• 192374-15-5 (R,R)-Hydroxybupropion 
• 291275-48-4 Trifluoro-methanesulfonic acid (R)-2-(3-chloro-phenyl)-1-methyl-2-oxo-ethyl ester 
• 291275-47-3 Trifluoro-methanesulfonic acid (S)-2-(3-chloro-phenyl)-1-methyl-2-oxo-ethyl ester 
• 1231951-92-0 (2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol 

Relevant articles and documents

Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate

A stereospecific method for the synthesis of enantiopure α-aminoketone from its corresponding α-hydroxy-ketone via the triflate intermediate is discussed. This strategy provides a rapid and efficient route for the preparation of either enantiomer of bupro

Palladium-catalysed alkene chain-running isomerization

We report a method for palladium-catalysed chain-running isomerization of terminal and internal alkenes. Using an air-stable 2,9-dimethylphenanthroline-palladium catalyst in combination with NaBAr4 promoter, olefins are converted to the most stable double bond isomer at -30 to 20 °C. Silyl enol ethers are readily formed from silylated allylic alcohols. Fluorinated substituents are compatible with the reaction conditions, allowing the synthesis of fluoroenolates. Catalyst loading as low as 0.05% can be employed on a gram scale.

HYDROXYBUPROPION ANALOGUES FOR TREATING DRUG DEPENDENCE

The invention provides hydroxybupropion analogues capable of inhibiting the reuptake of one or more monoamines and/or acting as antagonists at nicotinic acetylcholine receptors. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin and/or may selectively bind to one or more nicotinic acetylcholine receptor subtypes. Such compounds may be used to treat conditions that are responsive to modification of monoamine levels and/or antagonism of nicotinic acetylcholine receptors, including drug dependency, depression, and obesity.

Synthesis and characterization of in vitro and in vivo profiles of hydroxybupropion analogues: Aids to smoking cessation

To create potentially superior aids to smoking cessation and/or antidepressants and to elucidate bupropions possible mechanisms of action(s), 23 analogues based on its active hydroxymetabolite (2S,3S)-4a were synthesized and tested for their abilities to inhibit monoamine uptake and nAChR subtype activities in vitro and acute effects of nicotine in vivo. The 3′,4′-dichlorophenyl [(±)-4n], naphthyl (4r), and 3-chlorophenyl or 3-propyl analogues 4s and 4t, respectively, had higher inhibitory potency and/or absolute selectivity than (2S,3S)-4a for inhibition of DA, NE, or 5HT uptake. The 3′-fluorophenyl, 3′-bromophenyl, and 4-biphenyl analogues 4c, 4d, and 4l, respectively, had higher potency for antagonism of α4β2-nAChR than (2S,3S)-4a. Several analogues also had higher potency than (2S,3S)-4a as antagonists of nicotine-mediated antinociception in the tail-flick assay. The results suggest that compounds acting via some combination of DA, NE, or 5HT inhibition and/or antagonism of α4β2-nAChR can potentially be new pharmacotherapeutics for treatment of nicotine dependence.