108794-01-0

Basic information

• Product Name: 4-Pentenoic acid, 2-hydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2S)-
• CAS NO: 108794-01-0
• Molecular Formula: C21H30O3
• Molecular Weight: 330.467
• Mol File: 108794-01-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-Pentenoic acid, 2-hydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentenoic acid, 2-hydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2S)-(108794-01-0)
• EPA Substance Registry System: 4-Pentenoic acid, 2-hydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2S)-(108794-01-0)

Safety Data

• Hazardous Substances Data: 108794-01-0(Hazardous Substances Data)

Upstream product

• 187737-37-7 propene 
• 84312-20-9 (1R,3R,4S)-8-phenylmenthyl glyoxylate 
• 65253-04-5 (-)-8-phenylmenthol 
• 89-82-7 pulegone 
• 56680-79-6 allyloxyacetyl chloride 
• 24850-33-7 allyltributylstanane 
• 108794-12-3 <1R-(1α,2β,5α)>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl dihydroxyacetate 
• 106-95-6 allyl bromide 
• 109385-12-8 Allyloxy-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 72526-00-2 (-)-8-phenylmenthyl acrylate 
• 104197-95-7 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate 
• 80595-59-1 bromoacetic acid (-)-8-phenylmenthol ester 

Relevant articles and documents

Enantioselective synthesis of unsaturated α-hydroxy acids

(S)- and (R)-2-Hydroxyhex-5-enoic acid and (S)- and (R)-2-hydroxyhept- 6-enoic acid were prepared in excellent yields and enantiomeric excesses (>99% ee) from the corresponding α-keto esters by the enzyme catalysed hydrolysis of the ester and reduction of the ketone in a single pot process. The enantioselective synthesis of (S)-2-hydroxypent-4-enoic acid was achieved via reaction of the reagent derived from allyl bromide and indium metal with the hydrate of 8-phenylmenthyl glyoxalate in water.

Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: Synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl- 4-butanolide

The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4- butanolide 13 is presented.

ASYMMETRIC INDUCTION IN THE ENE REACTION OF GLYOXYLATE ESTERS OF 8-PHENYLMENTHOL

We recently communicated (J.K.Whitesell, A.Bhattacharya, D.A.Aguilar and K.Henke, J.Chem.Soc.Chem.Commun. 989 (1982)) a highly efficient and effective method for the control of absolute stereochemistry through asymmetric induction in the ene reaction the chiral glyoxylate 1 with alkenes.We now have accumulated sufficient information on this process in terms of both its mechanistic details as well as its scope and applicability to a variety of situations that warrants a more complete presentation of these reactions.