192199-24-9

Basic information

• Product Name: (1R,3R,4S)-8-phenylmenthyl 2-methylacetoacetate
• Synonyms: (1R,3R,4S)-8-phenylmenthyl 2-methylacetoacetate
• CAS NO: 192199-24-9
• Molecular Weight: 330.467
• Mol File: 192199-24-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R,3R,4S)-8-phenylmenthyl 2-methylacetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3R,4S)-8-phenylmenthyl 2-methylacetoacetate(192199-24-9)
• EPA Substance Registry System: (1R,3R,4S)-8-phenylmenthyl 2-methylacetoacetate(192199-24-9)

Safety Data

• Hazardous Substances Data: 192199-24-9(Hazardous Substances Data)

Upstream product

• 90358-31-9 (+)-(1R,2S,5R)-8-phenylmenthyl 3-oxobutanoate 
• 74-88-4 methyl iodide 
• 65253-04-5 (-)-8-phenylmenthol 
• 609-14-3 2-acetylpropanoic acid ethyl ester 

Downstream Products

• 154903-59-0 (1R,4aS,10aR)-6-Methoxy-1,4a-dimethyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 154903-60-3 (-)-Phenylmenthyl (+)-O-methylpodocarpate 
• 10037-26-0 O-methylpodocarpic acid 
• 16826-86-1 12-O-methylpodocarpol 
• 16826-83-8 12-O-methylpodocarpal 
• 444667-38-3 2-Methylene-3-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 428453-85-4 (6E,10E)-13-Hydroxy-2,6,10-trimethyl-3-oxo-trideca-6,10-dienoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Relevant articles and documents

A Convenient Synthesis of A-Ring-Functionalized Podolactones. Revision of the Structure of Wentilactone B

(Matrix Presented) A new route to podolactones functionalized in the A ring has been achieved. Two key steps were employed in this synthesis, the construction of the bicyclic skeleton via a Mn(III)-mediated radical cyclization and the transformation of this bicyclic intermediate into the tetracyclic podolactone skeleton through a Pd (II)-mediated bislactonization of the corresponding conjugate diene. The reported synthesis of 3β-hydroxy-13,14,15,-16-tetranorlabda-7,9(11)-dien-(19,6β),(12,17)- diolide (1) let us reassign the structure of wentilactone B, for which structure 1 was wrongly reported.

Asymmetric Induction in Mn(III)-Based Oxidative Free-Radical Cyclizations of Phenylmenthyl Acetoacetates and 2,5-Dimethylpyrrolidine Acetoacetamides

Mn(III)-based oxidative free-radical cyclization of phenylmenthyl ester 1e afforded 90percent of 13 with 86percent de.Cyclization of 31b provided 56percent of (+)-podocarpic acid precursor 32e with 82percent de.The direction of de was opposite in these two cases.Oxidative cyclization of α-methyl β-keto ester 44b gave a 1:1.6 mixture of 46b and 47b while α-propyl β-keto ester 44d produced a >10:1 mixture of 46d and 47d indicating that the extent and direction of de is dependent on the size of the α-substituent.The reaction proceeds through transition states 12 and 56 with large α-substituents and through transition states 19 and 57 with small α-substituents.The de depends on the double-bond substitution pattern as shown by the decreased de with 37b and 37d, and selectivity in the 5-exo cyclization of 64b, 65b, 70b, and 71b is low.