905589-59-5

Basic information

• Product Name: (3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate
• Synonyms: (3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate
• CAS NO: 905589-59-5
• Molecular Weight: 312.58
• Mol File: 905589-59-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate(CAS DataBase Reference)
• NIST Chemistry Reference: (3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate(905589-59-5)
• EPA Substance Registry System: (3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate(905589-59-5)

Safety Data

• Hazardous Substances Data: 905589-59-5(Hazardous Substances Data)

Upstream product

• 545-06-2 trichloroacetonitrile 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 

Downstream Products

• 212051-39-3 methyl 3-(3,4-dimethoxy-benzyloxy)-2-(R)-methyl-propionate 
• 905589-58-4 (2S,3R)-1-tert-butyldimethylsilyl-2-chloro-3-(3,4-dimethoxybenzyl)-4-methoxymethyl-butane-1,3,4-triol 
• 395069-65-5 4-[2-(4-Bromomethyl-phenyl)-ethoxymethyl]-1,2-dimethoxy-benzene 
• 185300-91-8 (3,4-Dimethoxy-benzyloxy)-acetic acid methyl ester 
• 105014-95-7 1-[(2R,3R,3aR,9aR)-3-(3,4-Dimethoxy-benzyloxy)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-3-(2-methoxy-ethoxymethyl)-1H-pyrimidine-2,4-dione 
• 101538-31-2 3,4-dimethoxybenzyl benzoate 
• 5888-51-7 4-ethylveratrole 
• 1221294-62-7 C₃₄H₄₈O₇Si 
• 105038-58-2 Phosphoric acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(3,4-dimethoxy-benzyloxy)-5-[3-(2-methoxy-ethoxymethyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 5-chloro-quinolin-8-yl ester 
• 105038-56-0 1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(3,4-dimethoxy-benzyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-3-(2-methoxy-ethoxymethyl)-1H-pyrimidine-2,4-dione 
• 105014-96-8 1-[(2R,3R,4R,5R)-3-(3,4-Dimethoxy-benzyloxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-3-(2-methoxy-ethoxymethyl)-1H-pyrimidine-2,4-dione 
• 185300-92-9 (2S,5R,6S,7R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-1-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-6-methyl-octane-1,3-dione 
• 185300-83-8 (S)-3-[(2S,3R,5R,6S,7R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-3-hydroxy-6-methyl-octanoyl]-4-isopropyl-oxazolidin-2-one 
• 1054698-71-3 (S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one 

Relevant articles and documents

Synthesis of 1,1′-diarylethanes and related systems by displacement of trichloroacetimidates with trimethylaluminum

Benzylic trichloroacetimidates are readily displaced by trimethylaluminum under Lewis acid promoted conditions to provide the corresponding methyl substitution product. This method is a convenient way to access 1,1′-diarylethanes and related systems, which play a significant role in medicinal chemistry, with a number of systems owing their biological activity to this functionality. Most benzylic substrates undergo ready displacement, with electron deficient systems being the exception. The use of an enantiopure imidate showed significant racemization, implicating the formation of a cationic intermediate.

Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1′-diarylbutyl pharmacophore

1,1′-Diarylbutyl groups are a common pharmacophore found in many biologically active small molecules. To access these systems under mild conditions, the reaction of diarylmethyl trichloroacetimidates with allyltributylstannanes was explored. Simply heating allyltributylstannane with the trichloroacetimidate resulted in substitution of the imidate with an allyl group. Unlike other methods used to access these systems, no strong base, transition metal catalyst, Br?nsted acid or Lewis acid promoter was required to affect the transformation. Conversions are best with electron rich benzylic trichloroacetimidate systems, where excellent yields are achieved just by refluxing the reactants together in nitromethane.

Synthesis of homo- and heteroprotected furcated units for modular chemistry

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