72526-00-2

Basic information

• Product Name: 2-Propenoic acid, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• Synonyms: (-)-(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate;(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl prop-2-enoate;(1R,2S,5R)-5-methyl-2-(2-phenylprop-2-yl)cyclohexyl acrylate;(-)-8-phenylmenthyl dimethyl phosphonoacetate;5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate;2-Propenoic acid,(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester;(+)-8-phenylmenthyl acrylate;Acrylic acid,[5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl] ester
• CAS NO: 72526-00-2
• Molecular Formula: C19H26O2
• Molecular Weight: 286.414
• Mol File: 72526-00-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester(72526-00-2)
• EPA Substance Registry System: 2-Propenoic acid, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester(72526-00-2)

Safety Data

• Hazardous Substances Data: 72526-00-2(Hazardous Substances Data)

Upstream product

• 65253-04-5 (-)-8-phenylmenthol 
• 814-68-6 acryloyl chloride 
• 1427281-83-1 (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 
• 88002-15-7 Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester 
• 79-10-7 acrylic acid 

Downstream Products

• 84312-20-9 (1R,3R,4S)-8-phenylmenthyl glyoxylate 
• 185515-94-0 <1R-(1α,2β,5α)>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-hydroxy-3-nitropropanoate 
• 676566-70-4 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1R,4S,5R)-4-hydroxy-2-[(4-methylphenyl)sulfonyl]-3-oxo-2-azabicyclo[2.2.2]oct-7-ene-5-carboxylate 
• 635678-43-2 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl-(2,3-dibromo)propionate 
• 880866-46-6 tetrahydro-pyrrolo[1,2-b]isoxazole-2,3a-dicarboxylic acid 3a-tert-butyl ester 2-[5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester 
• 1065272-12-9 C₄₁H₄₈F₆N₂O₅ 
• 1065272-14-1 C₄₁H₄₈F₆N₂O₅ 
• 1431164-77-0 (-)-(1R,2S,5R)-8-phenylmenthyl (2R)-4-oxo-1-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 
• 88146-33-2 (1R)-3-Methylencyclopentancarbonsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester 
• 88146-36-5 (1S)-3-Methylencyclopentancarbonsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester 
• 111832-23-6 Oxirane-2-carboxylic acid (1S,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Relevant articles and documents

Stereoselective synthesis of novel C-3 functionalized 3-sulfonyl-β-lactams: Promising biologically active heterocyclic scaffolds

An efficient and operationally simple strategy for the stereoselective synthesis of novel C-3 functionalized 3-sulfonyl-β-lactam heterocycles is described. The C-3 functionalized 3-phenyl/benzylsulfonyl-β-lactams 3/3′, 5/5′ has been synthesized via Michael addition using different Michael acceptors on trans-3-phenyl/benzylsulfonyl-β-lactams 2(a–f) using K2CO3as a base and acetonitrile/DMF as solvents. The reaction furnished exclusively cis-β-lactam adducts 3(a–r) using sterically less hindered Michael acceptors. Further, the effect of steric bulk and chiralilty of Michael acceptors was explored to achieve target C-3 functionalized β-lactams 3(s-u)/3′(s-u) and 5(a–c)/5′(a–c). The structural and stereochemical analysis of novel β-lactams were carried out using FT-IR, NMR (1H,13C,1H-1H COSY,1H-13C COSY and13C DEPT-135), elemental analysis (CHNS), mass spectrometry (EIMS and LCMS) in representative cases and single crystal X-ray crystallographic studies (3e). The cis or trans configuration of the Michael acceptor (E) at C-3 was assigned with respect to C4-H.

The origin of stereoselectivity in cycloaddition reactions promoted by stereoisomers of 8-phenylmenthyl glyoxylate oxime

A structural study of three synthesized stereoisomeric oximes, (-)-8-phenylmenthyl glyoxylate oxime (8-PMGO), (+)-8-phenylneomenthyl glyoxylate oxime (8-PnMGO), and (-)-8-phenylisoneomenthyl glyoxylate oxime (8-PinMGO), was performed by means of variable temperature 1H NMR spectroscopy, X-ray crystallography, and ab initio calculations. It was found that in 8-PMGO a conformation where the phenyl and oxime moieties are stacked is significantly favored, whereas in the other stereoisomers this preference was not so evident. The conformational differences found between the isomers were used to rationalize the outcome of the reaction (simultaneous 1,3-cycloaddition and aza-Diels-Alder reaction) between the referred oximes and cyclopentadiene, in which the stereoselectivity was evaluated and found to be nicely reproduced by a simple conformational analysis. The global results indicate that the stereoselectivity of the studied oximes, a bit higher for 8-PMGO, originates from their particular conformational distribution, in which the phenyloxime aromatic interaction plays a decisive role.

Structure-activity relationship studies optimizing the antiproliferative activity of novel cyclic somatostatin analogues containing a restrained cyclic β-amino acid

The cyclic somatostatin analogue cyclo[Pro1-Phe 2-D-Trp3-Lys4-Thr5-Phe6] (L-363,301) displays high biological activity in inhibiting the release of growth hormone, insulin, and glucagon. According to the sequence of L-363,301, we synthesized a number of cyclic hexa- and pentapeptides containing nonnatural α- and β-amino acids. The N-fluorenylmethoxycarbonyl protected cyclic β-amino acid [1S, 2S, 5R]-2-amino-3,5-dimethyl-2-cyclohex-3-enecarboxylic acid (cβAA), for the replacement of the Phe6-Pro1 moiety of L-363,301, was synthesized in two steps by an enantioselective multicomponent reaction using (-)-8-phenylmenthol as a chiral auxiliary. The resulting peptide cyclo[cβAA1-Tyr2-D-Trp 3-Nle4-Thr(Trt)5] (Trt = triphenylmethyl) shows high antiproliferative effects in an in vitro assay with A431 cancer cells. The same peptide without the Trt group does not reveal any biological activity, whereas L-363,301 and closely related hexapeptides show only minor activity. By comparison of the solution structure of cyclo[cβAA1-Tyr 2-D-Trp3-Nle4-Thr(Trt)5] with the structure of L-363,301, a nearly perfect match of the βII′-turn region with D-Trp in the i + 1 position was observed. The cyclic β-amino acid cβAA is likely needed for the bioactive conformation of the peptide.