Cinnamic acid methyl-, ester

Ruthenium complexes of (129) and (130)336 were investigated for the asymmetric hydrogenation of prochiral 2-R-propenoic acids (Scheme 62a) rhodium complexes of these ligands were used for hydrogenation of acetoamido-cinnamic acid methyl ester (Scheme 62c) and hydrogenation of acetophenone-benzylamine (Scheme 62b). The results obtained with these... 

Methyl clnnamate Cinnamic acid, methyl ester (8) 2-Propeno1c acid, 3-pheny1-, methyl ester (9) (103-26-4)... 

The strategy is impressively simple the phthalazine derivative 15 can readily be prepared from quinine in one step. Being a divinyl derivative, it can be submitted as a cross-linking unit in the radical polymerization of methyl methacrylate (MMA) or 2-hydroxy methacrylate (HEMA). Thereby, an immobilized (DHQ-PHAL) derivative 16 is obtained, which is suited for the asymmetric dihydroxylation of frantr-stilbene (>99 % ee) and ( )-cinnamic acid methyl ester (>99 % ee. Table 1). The insoluble catalyst can be recovered by simple filtration, and its repeated... 

The anionic tenside chiral diphosphine 8 was used to generate rhodium catalysts for the hydrogenation of the prochiral olefm (Z)-2-(N-acetamido)cinnamic acid methyl ester in micellar ethyl acetate/H20 two-phase systems [42], The yield (100%) and enantiomeric excess (69%) were considerably higher than those observed with the tetrasulfonated bis(diphenylphosphino)pentane (32% yield and 20% ee) and the reaction time was shorter (1.5 versus 20 h) [42]. 

D Auria, M. and Vantaggi, A., Photochemical dimerization of methoxy substituted cinnamic acid methyl esters. Tetrahedron, 48, 2523,1992. 

Methyl, ethyl, n-propyl, isopropyl, n-hutyl, benzyl, cyclohexyl esters of formic, acetic, oxalic, succinic, tartaric, citric, benzoic, salicylic (and other substituted benzoic acids), phthalic and cinnamic acids phenyl esters of acetic, benzoic and salicylic acids. 

N,N -Bis(1-methylethyl)-6-(methylthio-1,3,5-triazine-2,4-diamine. SeePrometryn Bis (1-methylethyl) naphthalene. See Diisopropyl naphthalene 3-[2,4-Bis (i-methylethyl) phenyl]-2-propenoic acid, methyl ester. See Diisopropyl methyl cinnamate... 

Synonyms Cinnamic acid, isobutyl ester Isobutyl-P-phenylacrylate lsobutyl-3-phenylpropenoate 2-Methylpropyl 3-phenyl-2-propenoate 3-Phenyl-2-propenoic acid, 2-methyl propyl ester Empirical C13H16O2 Formula C4H900CCH CHC6Hs... 

Phenyl-2-propenoic acid 3-methylbutyl ester. See Isoamyl cinnamate 3-Phenyl-2-propenoic acid methyl ester. See Methyl cinnamate... 

Depending on the reaction conditions and the nature of the ester side chain in the cinnamates, the resorc[4]arenes can adopt different conformational states, namely, 1,2-altemate, 1,3-altemate, or flattened-cone). In particular, when ( )-2,4-dimethoxycinnamic acid methyl ester 1 was reacted with BF3 Et20 at room temperature, only the 1,2-altemate 2a and flattened-cone 2b stereoisomers were obtained in a 2 3 ratio and 75 % overall yield. In the 1,2-altemate conformation, the assignment of the 12- and 16-OMe signals, by INEPT experiments in conjunction with DIF NOE measurements, allowed to establish the correct stereochemistry at C(14). On the other hand, the presence in the H- and C-NMR spectra of only one signal for both external (H-5) and internal (H-28) aromatic protons and the related carbons, as well as a similar pattern for the methoxy group and the aliphatic... 

Model reactions with p-substituted methyl cinnamates 322 furnished the corresponding 3-aryl[2,3- H]propionic acid methyl esters 323 in chemical yields of 50-65% but in specific activities only 17-25% of theoretical. This outcome may be the result of the... 

As a general guide, however, it may be noted that the following have fairly easily recognisable odours methyl and ethyl formate methyl and ethyl acetate (apples) methyl and ethyl benzoate methyl salicylate (oil of winter-green) and ethyl salicylate methyl and ethyl cinnamate. (It is however usually impracticable to distinguish by odour alone between the methyl and ethyl esters of a particular acid.) Methyl and ethyl o. alate, and methyl and ethyl phthalate are almost odourless. Succinic and tartaric esters have faint odours. 

Pyrolytic Decomposition. The pyrolytic decomposition at 350—460°C of castor oil or the methyl ester of ricinoleic acid spHts the ricinoleate molecule at the hydroxyl group forming heptaldehyde and undecylenic acids. Heptaldehyde, used in the manufacture of synthetic flavors and fragrances (see Elavors and spices Perfumes) may also be converted to heptanoic acid by various oxidation techniques and to heptyl alcohol by catalytic hydrogenation. When heptaldehyde reacts with benzaldehyde, amyl cinnamic aldehyde is produced (see Cinnamic acid, cinnamaldehyde, and cinnamyl... 

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. 

Esters can be obtained from halogenated olefins using a metal carbonyl catalyst (87), eg, /n j -l-bromo-2-phenylethylene is treated with nickel carbonyl in the presence of methanol to afford the corresponding methyl cinnamate (see Cinnamic acid). 

The add is obtained by the reduction of cinnamic acid by means of sodium amalgam. The acid is then esterified by the condensing action of a mineral acid in methyl alcohol solution. The ester is an oil of very sweet odour, and is very useful for flower bouquets. 

As shown in Schemes 10-44 and 10-45, two products may be formed in a Meerwein reaction Scheme 10-44 shows a simple aryl-de-hydrogenation of cinnamic aldehyde, whereas Scheme 10-45 shows an aryl-de-hydrogenation combined with the addition of HC1 to the double bond of the methyl ester of cinnamic acid. No systematic studies have been made as to which of the two products will be formed in a given reaction, what experimental conditions will favor one or the other product, and what substituents or other structural characteristics of the alkene influence the ratio of the two types of product. The addition product can, in most cases, easily be converted... 

The pure enzyme was tested for activity against several methylated phenolic and cinnamic acids (Table 2). The enzyme was active on methyl esters of cinnamic acids caffeio p-coumaric> ferulic, and is therefore termed a cinnamoyl esterase (CinnAE). 

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