16725-75-0

Basic information

• Product Name: 1-Butanone, 2-methyl-1-phenyl-, (R)-
• CAS NO: 16725-75-0
• Molecular Formula: C11H14O
• Molecular Weight: 162.232
• Mol File: 16725-75-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 1-Butanone, 2-methyl-1-phenyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butanone, 2-methyl-1-phenyl-, (R)-(16725-75-0)
• EPA Substance Registry System: 1-Butanone, 2-methyl-1-phenyl-, (R)-(16725-75-0)

Safety Data

• Hazardous Substances Data: 16725-75-0(Hazardous Substances Data)

Usage

Chemical compound

1-Butanone, 2-methyl-1-phenyl-, (R)-

Class

Phenethylamine

Use

Psychostimulant medication

Treatment for

Attention deficit hyperactivity disorder (ADHD) and narcolepsy

Mechanism of action

Increases dopamine and norepinephrine levels in the brain

Effects

Improves focus, attention, and impulse control

Potential for abuse

High

Dependence risk

High

Legal classification

Schedule II controlled substance in the United States

Upstream product

• 71-43-2 benzene 
• 91739-22-9 (2′S)-2-Methoxymethyl-1-((2R)-2-methyl-1-phenylbutylidenamino)pyrrolidine 
• 609815-86-3 Trimethyl-((Z)-2-methyl-1-phenyl-but-1-enyloxy)-silane 
• 100-47-0 benzonitrile 
• 177914-33-9 C₁₇H₁₉NOS 
• 93-55-0 1-phenyl-propan-1-one 
• 73798-17-1 (SS)-1-(N-methylphenylsulfonimidoyl)-2-phenyl-2-butanol 
• 108509-71-3 (R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-butan-1-one 
• 100-58-3 phenylmagnesium bromide 
• 77858-01-6 ((S)-1-Methoxymethyl-2-phenyl-ethyl)-[1-phenyl-but-(E)-ylidene]-amine 
• 74-88-4 methyl iodide 
• 81777-32-4 4-Methyl-benzenesulfinic acid [(R)-2-methyl-1-phenyl-but-(E)-ylidene]-amide 
• 75-03-6 ethyl iodide 
• 77857-99-9 ((S)-1-Methoxymethyl-2-phenyl-ethyl)-[1-phenyl-prop-(E)-ylidene]-amine 

Downstream Products

• 16725-77-2 (1R,2R)-2-methyl-1-phenylbutan-1-ol 
• 16725-79-4 (1S,2R)-2-methyl-1-phenylbutan-1-ol 
• 873998-30-2 2-bromo-2-methyl-1-phenylbutan-1-one 
• 938-87-4 2-methyl-1-phenyl-butan-1-one 

Relevant articles and documents

Stereocontrol in Preparation of Cyclopalladated Alkylaromatic Oximes and Evaluation of Their Stereoselective Esterase-Type Catalytic Activity

The stereochemistry of 2′-methylbutyrophenone oxime, the rates of ortho-palladation of its E- and Z-isomers, and catalytic activity of the respective Pd complexes were studied. The full stereoisomeric composition of oximes was established for the first time by means of supercritical fluid chromatography on chiral polysaccharide column. It was shown that enantiomeric excesses of both E/Z-isomers of (S)-2′-methylbutyrophenone oxime (1S) and (R)-2′-methylbutyrophenone oxime (1R) were equal to 92 ± 2. The cyclopalladation study revealed that while E-isomer is ortho-palladated very quickly its Z-counterpart does not enter this reaction. However, upon coordination to Pd(II), Z-oxime slowly isomerizes into E-form with fast subsequent cyclopalladation, so it was possible to perform ortho-palladation of E-oxime in kinetic resolution mode with removal of unreacted Z-oxime. Comparatively rare cis-structure of cyclopalladated oxime dimer was proved by means of single-crystal X-ray study. For the first time, it was shown that ortho-palladated chiral oximes behave as enantioselective catalyst in the hydrolysis of chiral esters.

Fluoride Anions in Self-Assembled Chiral Cage for the Enantioselective Protonation of Silyl Enol Ethers

The potential of Song's chiral oligoethylene glycols (oligoEGs) as catalysts was explored in the enantioselective protonation of trimethylsilyl enol ethers in combination with alkali metal fluoride (KF and CsF) and in the presence of a proton source. Highly enantioselective protonations of various silyl enol ethers of α-substituted tetralones were achieved, producing chiral α-substituted tetralones in full conversion and with up to 99% ee. The established protocol was successfully extended to the synthesis of biologically relevant chiral α-substituted chromanone and thiochromanone derivatives.

Non-destructive Removal of the Bornanesultam Auxiliary in α-Substituted N-Acylbornane-10,2-sultams under Mild Conditions: An Efficient Synthesis of Enantiomerically Pure Ketones and Aldehydes

α-Substituted N-acylbornane-10,2-sultams 6, 9, and 10 can be converted into enantiomerically pure ketones 5, 13, and 14, respectively, via a two-step procedure involving a known mercaptolysis reaction followed by an -mediated coupling of the resulting S-benzyl thioesters with Grignard reagents.Furthermore, enantiomerically pure aldehydes 23 can be obtained from α-substituted N-acylbornane-10,2-sultams 6 via a one-step reduction with (i-Bu)2AlH.No epimerization at the α-chiral center is observed during the cleavage reaction whereby the chiral auxiliary, bornane-10,2-sultam 1 or ent-1, was recovered.By using this methodology, several natural products or precursors thereof can be prepared.