159213-12-4

Basic information

• Product Name: (R)-2-Methyl-1-phenyl-3-heptanone
• Synonyms: (R)-2-Methyl-1-phenyl-3-heptanone
• CAS NO: 159213-12-4
• Molecular Formula: C₁₄H₂₀O
• Molecular Weight: 204.308
• Mol File: 159213-12-4.mol

Chemical Properties

• Boiling Point: 290.5±9.0 °C(Predicted)
• Appearance: /
• Density: 0.933±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (R)-2-Methyl-1-phenyl-3-heptanone(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Methyl-1-phenyl-3-heptanone(159213-12-4)
• EPA Substance Registry System: (R)-2-Methyl-1-phenyl-3-heptanone(159213-12-4)

Safety Data

• Hazardous Substances Data: 159213-12-4(Hazardous Substances Data)

Usage

Uses

Used in the Food and Beverage Industry:
(R)-2-Methyl-1-phenyl-3-heptanone is used as a flavoring agent for its sweet, fruity aroma that resembles the scent of raspberries, enhancing the taste and smell of various food and drink products.
Used in the Cosmetic and Perfume Industry:
Raspberry ketone is used as a fragrance component for its pleasant and appealing scent, contributing to the creation of captivating and long-lasting fragrances in cosmetics and perfumes.
Used in the Health and Wellness Industry:
(R)-2-Methyl-1-phenyl-3-heptanone is used as an ingredient in weight loss supplements due to its potential to increase the breakdown of fats in the body. However, more research is required to confirm its effectiveness and safety in this application.

Upstream product

• 109-72-8 n-butyllithium 
• 159345-06-9 (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethyl-3-phenylpropionamide 
• 7042-33-3 ethyl 2-methylcinnamate 
• 470676-68-7 (E)-2-methyl-1-phenyl-1-hepten-3-one 
• 100-52-7 benzaldehyde 
• 155852-53-2 N-methoxy-N-methyl-α-methylcinnamamide 
• 1380325-31-4 (R)-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethyl-3-phenylpropanamide 
• 100-39-0 benzyl bromide 
• 377092-88-1 (1R)-2-endo-[(2R)-methylhydrocinnamoyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 
• 123-62-6 propionic acid anhydride 

Relevant articles and documents

Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones

Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.

Pseudoephenamine: A practical chiral auxiliary for asymmetric synthesis

Unrestricted: Pseudoephenamine is introduced as a versatile chiral auxiliary and an alternative to pseudoephedrine in asymmetric synthesis. It is free from regulatory restrictions and leads to remarkable stereocontrol in alkylation reactions, especially in those that form quaternary carbon centers. Amides derived from pseudoephenamine exhibit a high propensity to be crystalline substances, and provide sharp, well-defined signals in NMR spectra. Copyright

Application of A Recyclable Pseudoephedrine Resin in Asymmetric Alkylations on Solid Phase

A pseudoephedrine resin has been successfully employed in asymmetric alkylations on solid phase. Immobilized pseudoephedrine amides are conveniently prepared by the one-step attachment of pseudoephedrine to Merrifield resin through the hydroxyl group and subsequent acylation on nitrogen. Deprotonation and alkylation of the resin-bound amides proceeds smoothly. Ketones and alcohols are cleaved from the resin in high enantiomeric excess and moderate to good overall yield. The parallel, asymmetric solid-phase synthesis of a small library of chiral ketones and alcohols has been carried out to illustrate the utility of the approach. Finally, the pseudoephedrine resin can be conveniently recycled and utilized with no significant loss in the yield or enantiomeric excess of the products.

Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase

(Equation Presented) Immobilized pseudoephedrine amides have been conveniently prepared by attachment of pseudoephedrine to Merrifield resin and acylation on nitrogen. Deprotonation and alkylation of the resin bound amides proceeds smoothly. Products were cleaved from the resin to give ketones and alcohols in high enantiomeric excess and moderate to good overall yield.

Alkylation of chiral α-hydroxy ketones derived from (1R)-(+)-camphor. An asymmetric variant of the classical acetylene route to carbonyl compounds

Equation presented The asymmetric version of the traditional route for transforming acetylene into α-branched carbonyl compounds is now feasible for the first time. The method involves the temporary attachment of camphor to acetylene and gives a remarkably high diastereo-and enantioselectivity.

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.

Synthesis of compounds with predetermined chirality

A method for synthesizing enantiomerically enriched chemical intermediates with predetermined chirality is described. The method comprises formation of a pseudoephedrine amide, followed by stereoselective alkylation at the alpha carbon. The chiral auxiliary can then be cleaved off, affording chiral end products useful for further transformations. The enantiomeric enrichment of the chiral end products may exceed 98%, and the chiral auxiliary can be recovered. Novel amides of pseudoephedrine used in this method are also disclosed.