82167-79-1

Basic information

• Product Name: 2-Butanone, 3-methyl-4-(phenylmethoxy)-, (R)-
• CAS NO: 82167-79-1
• Molecular Formula: C12H16O2
• Molecular Weight: 192.258
• Mol File: 82167-79-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-Butanone, 3-methyl-4-(phenylmethoxy)-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butanone, 3-methyl-4-(phenylmethoxy)-, (R)-(82167-79-1)
• EPA Substance Registry System: 2-Butanone, 3-methyl-4-(phenylmethoxy)-, (R)-(82167-79-1)

Safety Data

• Hazardous Substances Data: 82167-79-1(Hazardous Substances Data)

Upstream product

• 138058-66-9 (2R,4S,5R)-2-((S)-2-Benzyloxy-1-methyl-ethyl)-2,4-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 676-58-4 methylmagnesium chloride 
• 116652-76-7 (2R)-3-benzyloxy-N-methoxy-N-methyl-2-methylpropanamide 
• 88671-02-7 (R)-1-(benzyloxy)-2-methyl-3-[(tetrahydropyranyl)oxy]propan 
• 138058-63-6 (2R,4S,5R)-2-((R)-1-tert-Butylsulfanylcarbonyl-ethyl)-2,4-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 138058-72-7 (2R,4S,5R)-2-((R)-1-Methoxycarbonyl-ethyl)-2,4-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 138058-65-8 (2R,4S,5R)-2-((S)-2-Hydroxy-1-methyl-ethyl)-2,4-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 100-39-0 benzyl bromide 
• 88729-00-4 (-)-(R)-3-benzyloxy-2-methylpropionic acid 
• 63930-46-1 (S)-3-benzyloxy-2-methylpropan-1-ol 
• 89358-30-5 benzyl (2E)-4-bromobut-2-en-1-yl ether 
• 116505-20-5 3-Benzyloxy-2-methyl-propionyl chloride 
• 84801-99-0 (2R)-3-(Benzyloxy)-2-methylpropanoic acid chloride 
• 917-54-4 methyllithium 

Downstream Products

• 88671-03-8 (S)-4-(benzyloxy)-2,3-dimethyl-1-butene 
• 444804-99-3 (2R,5S)-1-benzyloxy-5-hydroxy-5-[(4S)-4-isopropenyl-cyclohex-1-enyl]-2-methyl-pentan-3-one 
• 62948-37-2 (+)-Phyllanthocin 
• 82167-80-4 (3R,3aS,6S,7aR)-3-Benzyloxymethoxy-3-benzyloxymethyl-2-((S)-4-hydroxy-3-methyl-2-methylene-butyl)-6-vinyl-octahydro-benzofuran-2-ol 
• 82189-56-8 C₃₂H₄₀O₅ 
• 82167-81-5 (2S,3R,3aS,5'S,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-methylene-6-vinylspiropyran> 
• 481048-22-0 (3R)-2,4-diiodo-3-methylbut-1-ene 
• 603040-95-5 C₁₂H₁₈O₂ 
• 16897-88-4 C₁₂H₁₈O₂ 
• 1453462-25-3 (2R,5S,6R,E)-1-(benzyloxy)-8-bromo-5-hydroxy-2,6-dimethylnon-7-en-3-one 
• 88671-21-0 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-2,3-dimethyl-but-3-enyl ester 
• 88671-20-9 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-2,3-dimethyl-but-3-enyl ester 
• 88671-06-1 methyl (2S,3R,3aS,5'R,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-oxospiropyran>-6-carboxylate 
• 88671-10-7 methyl (2S,3R,3aS,4'S,5'R,6S,7aR)-3-<(tert-butyldimethylsiloxy)methyl>-4'-<(E)-cinnamoyloxy>decahydro-3-hydroxy-5'-methylspiropyran>-6-carboxylate 

Relevant articles and documents

Lewis Base–Br?nsted Acid–Enzyme Catalysis in Enantioselective Multistep One-Pot Syntheses

Establishing one-pot, multi-step protocols combining different types of catalysts is one important goal for increasing efficiency in modern organic synthesis. In particular, the high potential of biocatalysts still needs to be harvested. Based on an in-depth mechanistic investigation of a new organocatalytic protocol employing two catalysts {1,4-diazabicyclo[2.2.2]octane (DABCO); benzoic acid (BzOH)}, a sequence was established providing starting materials for enzymatic refinement (ene reductase; alcohol dehydrogenase): A gram-scale access to a variety of enantiopure key building blocks for natural product syntheses was enabled utilizing up to six catalytic steps within the same reaction vessel.

Simple organocatalysts in multi-step reactions: An efficient one-pot Morita-Baylis-Hillman-type α-hydroxymethylation of vinyl ketones followed by the convenient, temperature-controlled one-pot etherification using alcohols

1,4-Diazabicyclo[2.2.2]octane (DABCO) was utilized as versatile catalyst in a one-pot synthesis: First, for the preparation of alcoholic formaldehyde solutions from para-formaldehyde catalysed by using low loadings of inexpensive DABCO. Second, for the fast α-hydroxymethylation of alkylic and aromatic vinyl ketones in high yields. In a third step, the same catalyst can be used for an optional, temperature controlled in situ etherification of the Morita-Baylis-Hillman product with various alcohols on a multi-gram scale in moderate to good overall yields and high purities. Furthermore, an application of the ether in the enantioselective synthesis of a common building block for total synthesis is shown, thus providing a gram-scale access from inexpensive bulk chemicals.

Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones

The use of pseudoephedrine as a practical chiral auxiliary for asymmetric synthesis is described in full. Both enantiomers of pseudoephedrine are inexpensive commodity chemicals and can be N-acylated in high yields to form tertiary amides. In the presence of lithium chloride, the enolates of the corresponding pseudoephedrine amides undergo highly diastereoselective alkylations with a wide range of alkyl halides to afford α-substituted products in high yields. These products can then be transformed in a single operation into highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones.