5333-29-9

Usage

Class of chemicals

Phenethylamines

Structural relation

Amphetamines

Physical state

White crystalline solid

Molecular weight

222.28 g/mol

Availability

Powder or tablet form

Properties

Stimulant and hallucinogenic

Effects

Euphoria, increased energy, altered perceptions

Medical use

Not approved

Legal status

Controlled substance in many countries

Potential issues

Abuse and dependence

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 38228-27-2 N,N-diethyl-3,5-dimethoxybenzamide 
• 17213-58-0 3,5-dimethoxybenzamide 
• 855469-97-5 2,4-dimethoxy-6-valeryl-benzoic acid 
• 3431-67-2 di-n-butylcadmium 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 38228-28-3 1-(1-hydroxypentyl)-3,5-dimethoxybenzene 
• 109-72-8 n-butyllithium 
• 140464-67-1 3,4,5-Trimethoxybenzaldehyde dibutyl acetal 
• 62381-25-3 C₁₀H₁₈LiNO₂ 
• 151-10-0 1,3-Dimethoxybenzene 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 109-65-9 1-bromo-butane 
• 19179-31-8 3,5-dimethoxy-benzonitrile 

Downstream Products

• 50833-08-4 3,5-Dimethoxyphenyl-di-n-butylkarbinol 
• 83816-40-4 Lithium; 5-(3,5-dimethoxy-phenyl)-nonan-5-olate 
• 22930-08-1 1,3-dimethoxy-5-(2-methylhexan-2-yl)benzene 
• 500885-51-8 2-butyl-2-(3,5-dimethoxy-phenyl)-[1,3]dithiolane 
• 330855-39-5 5-(2-butyl-[1,3]dithiolan-2-yl)-benzene-1,3-diol 
• 104388-14-9 1-(1-Butyl-1-methylselanyl-pentyl)-3,5-dimethoxy-benzene 
• 104388-21-8 1-(1,1-Dibutyl-pentyl)-3,5-dimethoxy-benzene 
• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 
• 500-66-3 Olivetol 
• 58545-48-5 (E)-1,3-dimethoxy-5-(pent-1-en-1-yl)benzene 
• 83816-36-8 5-(5-Methylnon-5-yl)resorcinol Dimethyl Ether 

Relevant academic research and scientific papers

Preparation method of 3,5-dihydroxyamylbenzene

The invention provides a preparation method of 3,5-dihydroxyamylbenzene. The preparation method comprises the following steps: with a 3,5-dialkoxy benzoate compound as a raw material, subjecting the 3,5-dialkoxy benzoate compound to reacting with valeronitrile to generate a beta-ketone nitrile compound, hydrolyzing a cyano group to generate a carboxylic acid compound, performing a decarboxylation reaction to obtain 3,5-dialkoxyphenylpentanone, performing Huang Ming-long reaction or catalytic hydrogenation to convert 3,5-dialkoxyphenylpentanone into 3,5-dialkoxyamylbenzene, and finally, reducing an alkoxy group into a phenolic hydroxyl group so as to obtain 3,5-dihydroxyamylbenzene. The preparation method provided by the invention overcomes the defects of high cost, complex route, low yield, poor purity and the like of traditional processes.

Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.

A simple synthesis of ketone from carboxylic acid using tosyl chloride as an activator

An effective process for the conversion of carboxylic acid to ketone has been discovered. In this process, carboxylic acid has been activated using p-toluene sulphonyl group. Under the optimized condition, aromatic, aliphatic heteroaromatic carboxylic acids have been proved to be good substrates for this methodology. The byproduct of this reaction can be removed very easily during work up process. Also, one equivalent of organometallic reagent is sufficient to complete this transformation.

Simple one pot synthesis of ketone from carboxylic acid using DCC as an activator

Simple one pot procedure for the conversion of carboxylic acid to ketone is described. Various carboxylic acids were converted to the corresponding ketones in excellent manner in presence of N,N′-dicyclohexylcarbodiimide (DCC) and organometallic reagents. Aromatic, heteroaromatic and aliphatic acids were converted to the corresponding ketones smoothly under the optimum conditions using organolithium reagents. In this process, desired products have been isolated from the crude reaction mixtures in moderate yields during the purification process.

Cannabinoid derivatives, methods of making, and use thereof

1′-substituted cannabinoid derivatives of delta-8-tetrahydrocannabinol, delta-9-tetrahydrocannabinol, and delta-6a-10a-tetrahydrocannabinol that have affinity for the cannabinoid receptor type-1 (CB-1) and/or cannabinoid receptor type-2 (CB-2). Compounds

Synthesis and testing of novel classical cannabinoids: Exploring the side chain ligand binding pocket of the CB1 and CB2 receptors

A series of C3 cyclic side-chain analogues of classical cannabinoids were synthesized to probe the ligand binding pocket of the CB1 and CB2 receptors. The analogues were evaluated for CB1 and CB2 receptor binding affinities relative to Δ8-THC. The C3 side-chain geometries of the analogues were studied using high field NMR spectroscopy and quantum mechanical calculations. The results of these studies provide insights into the geometry of the ligand binding pocket of the CB1 and CB2 receptors.

Selective para metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with n-butyl lithium-potassium tert-butoxide (LIC-KOR): Synthesis of 3,5-dimethoxy-4-methyl benzoic acid

The potassium salt of 3-methoxy and 3,5-dimethoxy benzoic acids undergoes deprotonation at the position para to the carboxylate group selectively when treated with LIC-KOR in THF at -78°C and it has been extended to the synthesis of 3,5-dimethoxy-4-methyl benzoic acid. (C) 2000 Elsevier Science Ltd.

Regioselective Reductive Electrophilic Substitution of Derivatives of 3,4,5-Trimethoxybenzaldehyde

The behavior of several protected derivatives of 3,4,5-trimethoxybenzaldehyde has been investigated under conditions of electron transfer from alkali metals in aprotic solvents.The 4-methoxy group can be regioselectively removed in good to high yield under such conditions, and an appropriate choice of the protecting group, metal, and solvent allows its substitution with a variety of electrophiles. 3,4,5-Trimethoxybenzaldehyde dimethyl acetal, 1, is the starting material of choice for a new general synthetic approach to several polysubstituted resorcinol dimethyl ethers.Investigation of the mechanism of demethoxymetylation, with the aid of labeling experiments, showed that reductive demethoxylation is strongly influenced by the nature of the aldehyde protective group employed.

Long Chain Phenols. Part 17. The Synthesis of 5-resorcinol, 'Cardol monoene,' and of 5-resorcinol Dimethyl Ether, 'Cardol diene' Dimethyl Ether

Two unsaturated compounds in the 'cardol' series, an important component phenol from Anacardium Occidentale, have been synthesised. 3,5-Dimethoxybenzaldehyde interacted with OH-protected 6-chlorohexan-1-ol in the presence of lithium to give, after acidic treatment, 1-(3,5-dimethoxyphenyl)heptane-1,7-diol which was hydrogenolysed selectively to 7-(3,5-dimethoxyphenyl)heptan-1-ol.Conversion into the bromide and alkylation of lithio-oct-1-yne gave 5-(pentadec-8-ynyl)resorcinol dimethyl ether which was selectively converted into the 8-(Z)-alkene.Dmethylation with lithium iodide gave 5-resorcinol which was identical to 'cardol monoene'.Reaction of 7-(3,5-dimethoxyphenyl)heptyl bromide with lithium derivative of OH-protected propargyl alcohol, gave after acidic treatment 10-(3,5-dimethoxyphenyl)dec-2-yn-1-ol, the bromide of which with pent-1-ynylmagnesium bromide afforded 5-pentadec-8,11-diynylresorcinol dimethyl ether.Selective hydrogenation yielded 5-resorcinol dimethyl ether identical with the dimethyl ether of 'cardol diene.'

ADDITION OF CARBON NUCLEOPHILES TO ARENE-CHROMIUM COMPLEXES

The electrophilic reactivity of arenes coordinated to the chromium tricarbonyl unit has been developed into several distinct methods for coupling carbon nucleophiles with aromatic rings.Addition of the nucleophile produces stable η-cyclohexadienyl chromium complexes which can be oxidized to induce loss of the endo hydrogen and the metal, overall nucleophilic substitution for hydrogen.Alternatively, the intermediate can be protonated and the resulting cyclohexa-1,3-diene can be detached from the chromium, effecting nucleophilic addition with reduction of one double bond.If a halogen (F, Cl) is present as a ring substituent, and if the nucleophile can migrate about the arene ligand, then loss of halide can occur parallel with classical nucleophilic aromatic substitution for halogen in electron-deficient haloarenes.With substituted arenes, the regioselectivity of addition becomes important and is often very high.Particularly useful are strong resonance donor substituents (RO-, R2N-, F-) where selectivity for meta attack is high.Indole provides an excellent example of selective activation, as the six-membered ring complexes selectively and is then susceptible to nucleophilic substitution, predominantly at the 4 and 7 positions.Substitution for halogen is a somewhat limited process and depends upon the nature of the nucleophile.Very reactive nucleophiles add to unsubstituted positions and are often slow to isomerize to the ipso position from which loss of halide can occur.