90358-31-9

Basic information

• Product Name: (+)-(1R,2S,5R)-8-phenylmenthyl 3-oxobutanoate
• Synonyms: (+)-(1R,2S,5R)-8-phenylmenthyl 3-oxobutanoate
• CAS NO: 90358-31-9
• Molecular Weight: 316.441
• Mol File: 90358-31-9.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (+)-(1R,2S,5R)-8-phenylmenthyl 3-oxobutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1R,2S,5R)-8-phenylmenthyl 3-oxobutanoate(90358-31-9)
• EPA Substance Registry System: (+)-(1R,2S,5R)-8-phenylmenthyl 3-oxobutanoate(90358-31-9)

Safety Data

• Hazardous Substances Data: 90358-31-9(Hazardous Substances Data)

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 65253-04-5 (-)-8-phenylmenthol 
• 105-45-3 acetoacetic acid methyl ester 
• 2033-24-1 cycl-isopropylidene malonate 
• 75-36-5 acetyl chloride 
• 141-97-9 ethyl acetoacetate 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 

Downstream Products

• 1031781-51-7 C₂₀H₂₆N₂O₃ 
• 126421-82-7 (1R,2S,5R)-8-phenylmenthyl 3-acetamidobutanoate 
• 126421-76-9 (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (Z)-3-acetamido-2-butenoate 
• 192199-27-2 (R)-2-(4-Chloro-benzyl)-2-methyl-3-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 192199-25-0 (R)-2-Benzyl-2-methyl-3-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 192199-28-3 (R)-2-Methyl-3-oxo-2-phenethyl-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 264610-07-3 (E)-2-Chloro-9-(3-isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Relevant articles and documents

Mild and high-yielding synthesis of β-keto esters and β-ketoamides

In the presence of sodium acetate, the reaction between 2,2,6-trimethyl-4H-1,3-dioxin-4-one and secondary or tertiary alcohols (including chiral ones) or primary or secondary amines could be carried out in refluxing tetrahydrofuran, under much milder conditions than those described in the literature. In these new conditions, side products normally observed using the traditional protocol were avoided, and-keto esters and-ketoamides were normally obtained in quantitative yields.

Asymmetric synthesis of multifunctionalized pyrrolines by a ruthenium porphyrin-catalyzed three-component coupling reaction

(Chemical Equation Presented) Chiral multifunctionalized pyrrolines have been synthesized by a ruthenium porphyrin catalyzed three-component coupling reaction. In a one-pot reaction, ruthenium porphyrins catalyzed in situ generation of chiral azomethine ylides from chiral diazo esters and imines. Asymmetric 1,3-dipolar cycloaddition reactions of the chiral azomethine ylides with dipolarophiles afforded the corresponding pyrrolines in good yields and high diastereoselectivity (up to 92% de).

Diastereoselective alkylation of 8-phenylmenthyl 2- methylacetoacetate. Preparation of enantiomerically pure 4,4-disubstituted 2-pyrazolin-5-ones

Alkylation of (1R,3R,4S)-8-phenylmenthyl 2-methylacetoacetate with alkyl halides affords 2-alkyl-2-methylacetoacetates in diastereomeric ratios 72:28 to 85:15. The major R (at C-α) diastereoisomers are converted into enantiopure 4,4-disubstituted 2-pyrazolin-5-ones with recovery of the chiral inductor.