Methyl -3-phenyl-2-propenoate

C10H9NO4 methyl trans-3-(3-nitrophenyl)-2-propenoate 659-04-1 25.00 1.3140 2 19124 Cl OH1002 cis-2-methyl-3-phenyl-2-propenoic acid 15250-29-0 27.69 1.0799 2... 

Reports on enantioselectivc cyclopropanations involving simple diazoalkanes and optically active catalysts are scarce. The enantioselectivities are rather low89, with the exception of a bis(semicorrinato)copper catalyst. In the reactions of (E)- -phenyl-1 -propene and methyl ( )-3-phenyl-2-propenoate with diazomethane this catalyst90 induces ee s in the range of 70-75%. 

An excellent method for the diastereoselective synthesis of substituted amino acids is based on optically active bislactim ethers of cyclodipeptides as Michael donors (Schollkopf method, see Section 1.5.2.4.2.2.4.). Thus, the lithium enolates of bislactim ethers, from amino acids add in a 1,4-fashion to various a,/i-unsaturated esters with high diastereofacial selectivity (syn/anti ratios > 99.3 0.7-99.5 0.5). For example, the enolate of the lactim ether derivative 6, prepared from (S)-valine and glycine, adds in a highly stereoselective manner to methyl ( )-3-phenyl-propenoate a cis/trans ratio of 99.6 0.4 and a syn/anti ratio of 91 9, with respect to the two new stereogenic centers, in the product 7 are found105, los. 

E-3-[6 -Methyl-2 -(4"-nitrophenyl)phenyl]propenoic Acid Methyl Ester (21) [7]... 

Two peaks from the pyrogram, namely 2-ethylhexanol and benzoic acid phenyl ester do not seem to be formed from the poly(ethyl methacrylate) pyrolysis and are probably additives. Also, 2-methyl-2-propenoic acid methyl ester identified in the pyrogram is either a contaminant or an artifact of the analysis (carryover in the GC/MS system). 

Reaction of ketene dithioacetals 260 with thioamides gave 5-substituted 2-methyl(phenyl)-6-methylthio-4-thioxopyrimidine (262) (92H1573). The reaction mechanism involves the addition of the thioamide to the ketene dithioacetal 260 to afford 2-cyano-3-methylthio-3-thioamido-propenoni-trile or -propenoate intermediate, which cyclizes in situ by site-selective nucleophilic attack of the sulfur on the cyano group to give 6-imino-l,3-thiazine 261, which rearranged to 262 (Scheme 84). 

The regeneration of MV can also proceed in an electrochemical cell by Reaction [1]. For practical aspects see Section 6. If larger amoimts of enoates are reduced the regeneration of MV can also be carried out by Reaction [6a]. However, this reaction is not catalysed by C. tyrobutyricum. Therefore cells of Proteus vulgaris, P. mirabilis or C. thermoaceticum have to be added. As an example the reduction of 286 mmol ( -2-methyl-3-[4-(5-hep1ylpyrimidine-2-yl)-phenyl]-propenoate will be described (Table 3 No. 50 and Table 4 No. 22). 

Synonyms Methyl cinnamylate Methyl-3-phenyl propenoate 3-Phenyl-2-propenoic acid methyl ester... 

Propenamide-2-propenoic acid polymer. See Acrylic acid/acrylamide copolymer 2-Propenamide, N-[[4-[(4,7,7-trimethyl-3-oxobicyclo [2.2.1] hept-2-ylidene) methyl] phenyl] methyl]-, homopolymer. See Polyacrylamidomethyl benzylidene camphor Propenamidopropyltrimethylammonium chloride, polymer with propenoic acid, butenoic acid, and/or alkyl propenoates. See Acrylamidopropyltrimonium chloride/acrylates copolymer... 

Synonyms p-Menth-1-en-8-yl cinnamate (Z)-1-Methyl-1 -(4-methyl-3-cyclohexen-1 -yl) ethyl cinnamate Terpinyl p-phenylacrylate Terpinyl 3-phenyl propenoate... 

Dihydroxy-5-(l-oxopropyl)phenyl]-3-methyl-2-propenoic acid (E)... 

Methyl methacrylate homopolymet Methyl methacrylate polymer Methyl methacrylate polymers Methyl methacrylate resin. See Polymethyl methacrylate 2-Methyl-3-(para-methoxy phenyl)-ptopanal. See Canthoxal a-Methyl-ro-methoxypolydimethylsiloxane. See Dimethylsiloxane 1 -Methyl-4 (1 -methylethenyl) cyclohexene. See dl-Limonene 1-Methyl-4-(1-methylethenyl)-(S)-cyclohexene. See l-Limonene (R)-1-Methyl-4-(1-methylethenyl)-cyclohexene. See d-Umonene 1-Methyl-4-(1-methylethyl) benzene. See p-Cymene 1-Methyl-4-(1-methylethylidene) cyclohexene. See Terpinolene Methyl-2(methyl-2) oxybispropanol. See Dipropylene glycol Methyl-2-methyl-2-propenoate. See Methyl methacrylate Methylmorpholine 4-Methyl morpholine N-Methyl morpholine. See p-Methyl morpholine p-Methyl morpholine CAS 109-02-4 EINECS/ELINCS 203-640-0 UN 2535 (DOT)... 

Phenyl-2-propenoic acid [621 -82-9] commonly referred to as cinnamic acid, is a white crystalline soHd having a low intensity sweet, honeylike aroma. It has been identified as a principal constituent in the botanical exudates from Styrax IJquidamber orientalis) Benzoin Styrax ben in Pern Balsam [Myroxylon pereirae and Tolu Balsam (]Ayro>ylon balsamum) (4,5). In these, as well as numerous other natural products, it exists both as the free acid and in the form of one or more of its esters, as for example, methyl cinnamate, ben2yl cinnamate [103 1 -3] and cinnamyl cinnamate. 

However, the configuration of the major isomer obtained in the conjugate addition to methyl ( )-3-[(35,)-3-tot-butoxycarbonyl-2,2-dimcthyl-4-oxazolidinyl]-2-propenoate (entry 3) did not depend on the cuprate type alkyl-, vinyl-, 2-methylpropenyl-, phenyl-, and benzvl-cuprates induced the same sense of asymmetry, although the absolute configuration was not determined5. Here also, the stereochemical outcome was not dependent upon the geometry of the double bond. 

Conjugate Addition to Methyl ( >3-1(25,4A, 5.S>3-Benzyloxycarbonyl-4-methyl-5-phenyl-2-oxazolidinyl]-2-propenoate Typical Procedure7" ... 

Conjugate Addition. To a solution of 1.5 mmol of lithium dialkylcuprate at — 25 CC is added 1 mmol of methyl ( )-3-[(25,45,55)-3-benzyloxycarbonyl-4-methyl-5-phenyl-2-oxazolidinyl]-propenoate dissolved in 1 mL of dry diethyl ether. After 30 ntin at — 25 C, the mixture is treated with an aq NH3/NH4C1 pH 8 buffer solution and then stirred at r.t. for 15 min. After diethyl ether extraction, the organic layers are dried over Na,S()4 and filtered and the solvent is evaporated under reduced pressure. The crude products are checked by H- and l3C-NMR analyses in order to determine the diastereomer ratios (g 95 5) and then purified by flash chromatography (hexane/ethyl acetate 80 20) yield 70-72%. 

Propenoic acid, 2-methyl-3-phenyl-, butyl ester and Benzonitrile, 4-[(lE)-2-... 

Clive and coworkers have reported a total synthesis of calicheamicinone, the aglycon of the antitumor agent calicheamicin starting from the Diels-Alder reaction of methyl 3-nitro-propenoate with ketene acetal (Eq. 8.32).54 An asymmetric Diels-Alder reaction between ketene acetal presented in Eq. 8.32 and 3-nitropropenoate derived from (-)-8-phenyl-menthol affords the optically pure adduct, which can be converted into either enantiomer of calicheamicinone (Eq. 8.33).55... 

The 7,8-dihydrodiol of 5-MC (30b) was prepared from 8-hydroxy-5-MC by Method IV (60,103). It was necessary to utilize the 8-rather than the Ot-phenol (i.e. 8-HO-5-MC rather than 7-HO-5-MC), since oxidation of the latter with Fremy s salt was anticipated to take place predominantly in the para position. The 8-hydroxy-5-MC was prepared in our laboratories by a modification of the procedure in Figure 18. An alternative preparation of 8-hydroxy-5-MC via photocyclization of methyl 3-phenyl-2-(l-(6-methoxynaphthyl) propenoate has also recently been described (103). 

Fig. 10.23 X-ray structure of [Rh((R,R)-Et-DuPHOS)((Z)-3-N-acetylamino-3-(phenyl)-methyl propenoate)]+ and of[Rh((S,S)-DIPAMP)((Z)-2-benzoylamino-3-(3,4-dimethoxyphenyl)-methyl acrylate)]+ [62],...

ASYMMETRIC HYDROGENATION OF METHYL-(Z)-3-PHENYL-2-METHYL-CARBOXAMIDO-2-PROPENOATE USING (S)-(R)-DIAMINO FERRIPHOS AS THE CHIRAL LIGAND... 

Methyl 2-[3-(trifluoromethyl)phenyl]-4/7-furo[3,2-4]pyrrole-5-carboxylate 81a was made by thermolysis of the corresponding methyl 2-azido-3- 5-[3-(trifluoromethyl)phenyl]-2-furyl propenoate 378, which was formed by condensation of 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde 377 with methyl azidoacetate under sodium meth-oxide catalysis (Scheme 40) <2006KGS825>. 

Propenoic acid, 2-(bromomethyl)-, ethyl ester (17435-72-2), 66, 224 2-Propenoic acid, 2-(hydroxymethyl)-, ethyl ester (10029-04-6), 66, 224 2-Propenoic acid, 3-phenyl-, methyl ester (103-26-4), 68,155 2-PROPENOIC ACID, 3-(PHENYLSULFONYL)-, METHYL ESTER, (Z) (91077-67-7), 69, 169... 

SYNS FEMA No. 2698 METHYL CINNAMYLATE METHYL-3-PHENYLPROPENOATE 3-PHENYL-2-PROPENOIC ACID METHYL ESTER (9CI)... 

Similarly, (S)-fi-tyrosine hydrochloride is prepared by addition of the lithium amide of N-[(R)-l-phenylethyl]benzylamine to methyl ( )-3-[(4-benzyloxy)phenyl]-2-propenoate and subsequent hydrogenolysis and saponification24. Recently, a number of publications concerning related work has appeared139-146. The reaction of lithiated, mono-silylated 1-phenylethyl-amines with a-enones has also been studied130131. 

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