41497-31-8

Usage

Classification

Synthetic compound, belongs to the family of phenylpropanoids

Usage

Building block for the preparation of various pharmaceuticals and other organic compounds

Pharmacological properties

Potential use as a psychotropic substance

Structural features

a. Phenyl ring with two methoxy groups at positions 3 and 5
b. Propan-1-one group attached to the phenyl ring

Interest to researchers and chemists

Unique structural features and potential applications

Upstream product

• 721-04-0 2-phenoxy-1-phenylethanone 
• 925-90-6 ethylmagnesium bromide 
• 155586-39-3 (3,5-dimethoxyphenyl)-N-methoxy-N-methylcarboxamide 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 2386-64-3 ethylmagnesium chloride 
• 116114-87-5 3,5-dimethoxy-N-N-dimethylbenzamide 
• 203912-55-4 1-(3,5-dimethoxy-phenyl)-propan-1-ol 
• 41497-28-3 3,5-Dimethoxy-α-(methylsulfonyl)acetophenon 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 7664-93-9 sulfuric acid 
• 502924-54-1 3-(3,5-dimethoxy-phenyl)-2-methyl-3-oxo-propionic acid ethyl ester 
• 811-49-4 ethyllithium 
• 41497-29-4 3,5-Dimethoxy-α-(methylsulfonyl)propiophenon 

Downstream Products

• 54540-67-9 1-(3,5-Dimethoxyphenyl)-4-(4-fluorphenyl)-2-methyl-butan-1-on 
• 57860-53-4 1-(3,5-Dimethoxy-phenyl)-5-(4-fluoro-phenyl)-2-methyl-pentan-1-one 
• 89106-36-5 C₂₂H₂₈O₄ 
• 41395-10-2 1,3-dimethoxy-5-propylbenzene 
• 500-49-2 5-propyl-1,3-benzenediol 
• 31262-38-1 3-norpentyl-3-propyl-Δ⁸-tetrahydrocannabinol 
• 54540-69-1 2(3,5-Dimethoxyphenyl)-3-Methyl-5-(p-Fluorophenyl)Pentane 
• 1265594-39-5 4-(3,5-dimethoxyphenyl)-5-hydroxy-5-methyl-3-(2,4,6-trifluorophenyl)-2(5H)-furanone 
• 1265594-40-8 5-(3,5-dimethoxyphenyl)-6-methyl-4-(2,4,6-trifluorophenyl)-3(2H)-pyridazinone 
• 1265593-96-1 4-(3,5-dimethoxyphenyl)-3,6-dimethyl-5-(2,4,6-trifluorophenyl)pyridazine 
• 1265593-95-0 3-chloro-5-(3,5-dimethoxyphenyl)-6-methyl-4-(2,4,6-trifluorophenyl)-pyridazine 
• 1265594-09-9 3-chloro-5-(2-chloro-3,5-dimethoxyphenyl)-6-methyl-4-(2,4,6-trifluoro-phenyl)pyridazine 
• 28172-17-0 (6aS,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 72661-28-0 α-bromo-3,5-dimethoxypropiophenone 

Relevant academic research and scientific papers

Decomposition of a Β-O-4 lignin model compound over solid Cs-substituted polyoxometalates in anhydrous ethanol: acidity or redox property dependence?

Production of aromatics from lignin has attracted much attention. Because of the coexistence of C–O and C–C bonds and their complex combinations in the lignin macromolecular network, a plausible roadmap for developing a lignin catalytic decomposition process could be developed by exploring the transformation mechanisms of various model compounds. Herein, decomposition of a lignin model compound, 2-phenoxyacetophenone (2-PAP), was investigated over several cesium-exchanged polyoxometalate (Cs-POM) catalysts. Decomposition of 2-PAP can follow two different mechanisms: an active hydrogen transfer mechanism or an oxonium cation mechanism. The mechanism for most reactions depends on the competition between the acidity and redox properties of the catalysts. The catalysts of POMs perform the following functions: promoting active hydrogen liberated from ethanol and causing formation of and then temporarily stabilizing oxonium cations from 2-PAP. The use of Cs-PMo, which with strong redox ability, enhances hydrogen liberation and promotes liberated hydrogen transfer to the reaction intermediates. As a consequence, complete conversion of 2-PAP (>99%) with excellent selectivities to the desired products (98.6% for phenol and 91.1% for acetophenone) can be achieved.

PROCESS FOR THE PRODUCTION OF CANNABIDIOL AND DELTA-9-TETRAHYDROCANNABINOL

The present disclosure relates to the preparation of a cannabidiol compound or a derivative thereof. The cannabidiol compound or derivatives thereof can be prepared by an acid-catalyzed reaction of a suitably selected and substituted di-halo-olivetol or derivative thereof with a suitably selected and substituted cyclic alkene to produce a dihalo-cannabidiol compound or derivative thereof. The dihalo-cannabidiol compound or derivative thereof can be produced in high yield, high stereospecificity, or both. It can then be converted under reducing conditions to a cannabidiol compound or derivatives thereof.

A versatile synthesis of O-desmethylangolensin analogues from methoxy-substituted benzoic acids

The synthesis of O-desmethylangolensin (O-DMA) analogues from methoxy-substituted benzoic acids was described. Treatment of methoxy-substituted benzoic acids with 2 equiv of ethyllithium afforded methoxypropiophenones, which were subsequently transformed to ethyl 2-(methoxyphenyl)propionates via 1,2-rearrangement of the methoxyphenyl group using Pb(OAc)4/HClO4 in triethyl orthoformate. After hydrolysis with KOH, the 2-(methoxyphenyl)propionic acids were reacted with di- 2-pyridyl carbonate to afford 2-pyridyl 2-(methoxyphenyl)propionates, which were acylated with methoxy-substituted phenylmagnesium bromides to give methoxy-α-methyldesoxybenzoins. The methoxy groups of these compounds were selectively or fully demethylated using boron tribromide to give diverse O-DMA analogues in high yields.

FUNGICIDAL DIPHENYL-SUBSTITUTED PYRIDAZINES

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, wherein R1, R2, R3, R4a, R4b, R5, W, m and n are as defined in the disclosure. Also disclosed

QUINOLINE-DERIVED AMIDE MODULATORS OF VANILLOID VR1 RECEPTOR

This invention is directed to vanilloid receptor VR1 ligands. More particularly, this invention relates to quinoline-derived amides that are potent antagonists or agonists of VR1 which are useful for the treatment and prevention of inflammatory and other pain conditions in mammals.

Synthesis and pharmacological evaluation of ether and related analogues of Δ8-, Δ9-, and Δ9,11-tetrahydrocannabinol

The primary goal of this research was to synthesize a series of ether analogues of the cannabinoid drug class and to evaluate their agonist and antagonist pharmacological properties in either the mouse or the rat. Agonist and antagonist activity was evaluated in mice using a multiple-evaluation procedure (locomotor activity, tail-flick latency, hypothermia, ring immobility) and activity in rats determined in a discriminative stimulus paradigm. Additionally, novel analogues were evaluated for their ability to bind to the THC receptor site labeled by 3H-CP-55,940. None of the cannabinoid analogues were capable of attenuating the effects of Δ9-THC (3 mg/kg) in either the rat (doses up to 10 mg/kg) or in the mouse (doses up to 30 mg/kg). It also appears that the compounds with minimal in vivo activity are not mixed agonist/antagonists. These data would suggest that the phenolic hydroxyl is important for receptor recognition (binding) and in vivo potency. Additionally, cannabinoid methyl ethers previously considered inactive have been found to produce limited activity. Lastly, data suggest that Δ9,11- THC is more potent than previous reports indicated, and does possess pharmacological activity.

Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 2. Synthesis and estrogen receptor binding affinity of 4,4'-, 5,5'-, and 6,6'-disubstituted metahexestrols

The synthesis of symmetrically 4,4'-, 5,5'-, and 6,6'-disubstituted derivatives of the mammary tumor inhibiting antiestrogen metahexestrol [meso-3,4-bis(3-hydroxyphenyl)hexane] (1) are described [4,4'-disubstituents: F(2), Cl (3), Br (4), I (5), CH2N(CH3)2 (6), CH3 (7), CH2OCH3 (8), CH2OC2H5 (9), CH2OH (10), NO2 (11), NH2 (12), N(CH3)2 (13), COCH3 (14), and C2H5 (15); 5,5'-substituents: OH (16) and Cl (17); 6,6'-disubstituents: OH (18), F (19), Cl (20), and CH3 (21)]. The synthesis of 1-3, 16, and 19 was accomplished by reductive coupling of the propiophenones with TiCl4/Zn and subsequent hydrogenation of the cis-3,4-diphenylhex-3-enes. Compounds 17, 18, 20, and 21 were synthesized by coupling the 1-phenyl-1-propanols with TiCl3/LiAlH4 and separation of the meso diastereomers, while 4-15 were obtained by substitution of metahexestrol. The binding affinity of these compounds to the calf uterine estrogen receptor was measured relative to that of [3H]estradiol by a competitive binding assay. The test compounds showed relative binding affinity (RBA) values between 15 and 0.5% were evaluated in the mouse uterine weight test. They showed a similar (2 and 12), slightly increased (19 and 21), or strongly enhanced (7 and 20) estrogenicity compared to that of metahexestrol. Compounds 1, 2, 7, 12, and 21 exhibited antiestrogenic activity inhibiting the estrone-stimulated uterine growth (24 to 60% inhibition).