153390-68-2

Basic information

• Product Name: 2-(2,3-diMethoxyphenyl)propan-2-ol
• Synonyms: 2-(2,3-diMethoxyphenyl)propan-2-ol
• CAS NO: 153390-68-2
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.24294
• Mol File: 153390-68-2.mol

Chemical Properties

• Boiling Point: 97 °C(Press: 0.5 Torr)
• Appearance: /
• Density: 1.060±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane, Ethyl acetate, Methanol
• PKA: 14.30±0.29(Predicted)
• CAS DataBase Reference: 2-(2,3-diMethoxyphenyl)propan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,3-diMethoxyphenyl)propan-2-ol(153390-68-2)
• EPA Substance Registry System: 2-(2,3-diMethoxyphenyl)propan-2-ol(153390-68-2)

Safety Data

• Hazardous Substances Data: 153390-68-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(2,3-diMethoxyphenyl)propan-2-ol is used as an intermediate for the synthesis of Miltirone (M344500), an active component in Salvia miltiorrhiza. Miltirone has demonstrated potential as a phytotherapeutic agent in the treatment of alcohol dependence. It works by inhibiting the increase in the abundance of the mRNA for the α4 subunit of the GABAA receptor induced by ethanol withdrawal in cultured hippocampal neurons, thus helping to alleviate the symptoms of alcohol withdrawal and reducing the risk of relapse.

Upstream product

• 2150-42-7 methyl 2,3-dimethoxybenzoate 
• 75-16-1 methylmagnesium bromide 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 91-16-7 1,2-dimethoxybenzene 
• 67-64-1 acetone 

Downstream Products

• 2138-48-9 3-isopropylbenzene-1,2-diol 
• 850254-57-8 5-[2-(3-isopropyl-4,5-dimethoxy-phenyl)-2-methoxycarbonyloxy-ethyl]-4,4,5-trimethyl-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 850254-52-3 3-[2-(3-isopropyl-4,5-dimethoxy-phenyl)-2-methoxycarbonyloxy-ethyl]-3,4,4-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid methyl ester 
• 850254-59-0 3-[(E)-2-(3-Isopropyl-4,5-dimethoxy-phenyl)-vinyl]-3,4,4-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid methyl ester 
• 850254-56-7 4-[2-hydroxy-2-(3-isopropyl-4,5-dimethoxy-phenyl)-ethyl]-3,3,4-trimethyl-cyclohexanone 
• 850254-61-4 4-[(E)-2-(3-Isopropyl-4,5-dimethoxy-phenyl)-vinyl]-3,3,4-trimethyl-cyclohexanone 

Relevant articles and documents

Total Synthesis of (±)-Brussonol and (±)-Komaroviquinone via a Regioselective Cross-Electrophile Coupling of Aryl Bromides and Epoxides

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Synthesis of [6,6,m]-Tricyclic Compounds via [4+2] Cycloaddition with Au or Cu Catalyst

We synthesized [6,6,6]- and [6,6,7]-tricyclic compounds via intramolecular [4+2] cycloaddition by gold or copper catalysts. Substrates for cyclization were prepared by coupling reactions between eight types of diyne and four types of aromatic moieties. We have successfully synthesized eleven tricyclic compounds.

Total Synthesis of 1-Oxomiltirone and Arucadiol

A practical and efficient approach for the total synthesis of arucadiol and 1-oxomiltirone is reported. The key step which involves an intramolecular [4+2] cycloaddition catalyzed by gold(III) bromide or copper(II) triflate leads to the formation of 6-6-6-fused aromatic abietane core.

Convergent formal syntheses of (±)-brussonol and (±)-abrotanone via an intramolecular Marson-type cyclization

The formal convergent syntheses of both (±)-brussonol and (±)-abrotanone are reported. The key step involved the diastereoselective capture of an in situ generated oxocarbenium cation via an intramolecular Friedel-Crafts/Marson-type cyclization.

Esters as acylating reagent in a Friedel-Crafts reaction: Indium tribromide catalyzed acylation of arenes using dimethylchlorosilane

(Chemical Equation Presented) The Friedel-Crafts acylation of arenes with esters by dimethylchlorosilane and 10 mol % of indium tribromide has been achieved. The key intermediate RCOOSi(Cl)Me2 is generated from alkoxy esters with the evolution of the corresponding alkanes. The scope of the alkoxy ester moiety was wide: tert-butyl, benzyl, allyl, and isopropyl esters were successful. In addition, we demonstrated the direct synthesis of the indanone intermediate 11 of salviasperanol from ester 10.

A Rh(II)-catalyzed cycloaddition approach toward the synthesis of komaroviquinone

Using a rhodium(II)-catalyzed cyclization/cycloaddition sequence as the key reaction step, the icetexane core of komaroviquinone was constructed by an intramolecular dipolar-cycloaddition of a carbonyl ylide dipole across a tethered π-bond. The ylide was arrived at by cyclization of a rhodium carbenoid intermediate onto a proximal ester group. Efforts toward the preparation of the required precursor for elaboration to the natural product are discussed.

The total synthesis of pygmaeocin C

Making use of a recently developed intramolecular Friedel-Crafts alkylation process as the key operation, the first total synthesis, in racemic form, of pygmaeocin C has been achieved. Georg Thieme Verlag Stuttgart.