Isopropyl cinnamate

V-bromo-benzamide is a useful method for the synthesis of the side chain of paclitaxel (taxol) from isopropyl cinnamate.219... 

Table 9 Asymmetric aminohydroxylation of isopropyl cinnamate with 10 mol% osmium tetroxide...

The asymmetric amino-hydroxylation reaction provides a very short synthesis of the side chain of the anticancer agent Taxol . The substrate isopropyl cinnamate was converted to the chiral 1,2-hydroxy amide 98 as essentially a single enantiomer after recrystallization (5.96). Hydrolysis then gave the required amine, as its hydrochloride salt. 

Several other investigators have used the Sharpless chemistry to make the taxol side chain or analogs of it. Thus an N-benzoyl side chain was prepared in one step from rran -isopropyl cinnamate using benzamide-based AA in 60% yield with 3 1 regioselectivity and 97% ee (263). Side chains with heterocyclic rings at C-3 have been prepared by AA thus for example furan (264) and pyridine (265) analogs of the side chain have both been prepared by this method. 

Salvador has employed the polymer-supported bis(quimdyl)phthalazine 277 in the asymmetric aminohydroxylation of isopropyl cinnamate 278 in presence of N-chloromethanesulfonamide sodium salt and K2OSO4 in n-propanol/H20 (Scheme 113) [174]. The chemoselectmty, regioselectivity and ee are summarized in Table 17. Polymer 277 proved to be as efficient as homogeneous ligand in terms of activity, chemoselectivity and regioselectivity. Furthermore, the enantioselectivity was higher (87%) than those obtained with 273. 

Methylethyl 3-phenylpropenoate 1-Methylethyl 3-phenyl-2-propenoate. See Isopropyl cinnamate N-(1-Methylethyl)-2-propanamine. See Diisopropylamine... 

Propenoic acid, 3-phenyl-, 3-methylbutyl ester. See Isoamyl cinnamate 2-Propenoic acid, 3-phenyl-, 1-methylethyl ester. See Isopropyl cinnamate 2-Propenoic acid, 3-phenyl-, 3-phenyl-2-propenyl ester. See Cinnamyl cinnamate 2-Propenoic acid, 3-phenyl-, 3-phenylpropyl ester. See 3-Phenyl propyl cinnamate Propenoic acid polymer. See Polyacrylic acid 2-Propenoic acid, polymer with ethene. See Ethylene/acrylic acid copolymer 2-Propenoic acid, polymer with ethene, calcium salt. See Ethylene/calcium acrylate copolymer 2-Propenoic acid, polymer with ethene and ethenyl acetate. See Ethylene/acrylic acid/vinyl acetate copolymer 2-Propenoic acid, polymer with ethene, magnesium salt. See Ethylene/magnesium acrylate copolymer... 

Isoeugenyl phenylacetate Isojasmone a-Isomethylionone Isopropyl acetate p-Isopropylacetophenone Isopropyl benzoate Isopropyl butyrate Isopropyl cinnamate Isopropyl formate Isopropyl hexanoate... 

Isopropyl cinnamate Isopropyl-p-cresol 4-lsopropyl-5,5-dimethyl-1,3-dioxane Isopropyl hexanoate Isopropyl isovalerate Isopropyl octanoate p-lsopropylphenol p-Isopropylphenylacetaldehyde Isopropyl phenylacetate 2-(4-lsopropylphenyl) propionaldehyde... 

Hydroxycitronellal diethyl acetal 231-949-0 Isopropyl cinnamate 231-954-8 Fluorine 231-955-3 Aero-Lube ZC-480 Aquadag ... 

Diphenyl-sulfon-3,3 -disulfohydrazide C12H14O2 Benzyl tiglate Cinnamyl propionate Isopropyl cinnamate 1 -(p-Methoxyphenyl)-l -penten-3-one Phenethyl methacrylate Prenyl benzoate C12H14O3 Acetisoeugenol Ethyl methoxycinnamate Ethyl methyl phenylglycidate Eugenyl acetate 2-Phenoxyethyl methacrylate C12H14O4... 

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. 

In the Meerwein-Fonndorf reduction, cinnamaldehyde is reduced to cinnamic alcohol (yield ca. 85%) with isopropyl or benzyl alcohol in the presence of the corresponding aluminum alcoholate. 

The simplest araliphatic aldehyde, benzaldehyde and its 4-isopropyl homologue, cuminaldehyde, are used to a limited extent as fragrance and flavor materials. However, both compounds are used in large quantity for the production of the corresponding cinnamic and dihydrocinnamic aldehydes. 

Maltol Isobutyrate 2-Methoxy 3-(or 5- or 6-) Isopropyl Pyrazine 5H-5-Methyl-6,7 -dihydrocyclopenta[b]pyrazine 5-Methyl Furfural Methyl Furoate Methyl Hexanoate Methyl Isovalerate 5-Methyl 2-Phenyl 2-Hexenal Methyl Thiobutyrate Methyl Valerate P-Naphthyl Ethyl Ether Phenyl Ethyl Cinnamate Phenyl Ethyl Propionate Propyl Formate Propyl Mercaptan Salicylaldehyde 8-T etradecalactone 2-Tridecanone... 

Insoluble Sodium Metaphosphate, 52 Insoluble Sodium Polyphosphate, 52 Isoamyl Alcohol, 78 Isoamyl Benzoate, 78 Isoamyl Butyrate, 78 Isoamyl Phenyl Acetate, 78 Isoamyl Salicylate, 78 Isobutyl Cinnamate, 78 Isobutyl Isovalerate, 84 Isobutyraldehyde, 78 DL-Isoleucine, 30 L-Isoleucine, 31 Isopropyl Acetate, 80... 

Steric factors slow the rate of intermolecular addition of radicals to non-terminal alkenes such as 1, 2 and 10-12. In the absence of a Lewis acid additive, radical additions to the cinnamate 16 or the crotonate 17 are inefficient at —78 °C because radical reduction is faster than radical addition [21, 22, 25]. The reaction is also nonselective in the absence of Lewis acid. When stoichiometric amounts of Lewis acids are added to the reaction of isopropyl radical with 16, however, both the yield and the diastereoselectivity increase significantly. Thus, Yb(OTf)3 gives a product yield of 90% in a ratio of 18a/19a of 45 1. This record P diastereoselectivity in radical addition is comparable to or better than that obtained under ionic conditions. Use of catalytic Yb(OTf)3 (10 mol%) gives only a slight reduction in selectivity. Addition to the crotonate 17 promoted by Yb(OTf)3 gives a product ratio of 18b/ 19b of 25 1. 

Box et have isolated a new eudesmane sesquiterpenoid, rupestrol, which occurs naturally as its orthocinnamate (244) and cinnamate esters (245). The absolute configuration is based on the c.d. spectrum of the derivative (246) but this does not rule out unambiguously a structure with an a-isopropyl group and, furthermore, certain /i-acetoxy-ketones are known to exhibit anti-octant behaviour. Recently a number of eudesmane-based alkaloids have been isolated... 

Song CE, Oh CR, Roh EJ, Lee S-G, Choi JH (1999) One-Step Synthesis of Paclitaxel Side-Chain Precursor Benzamide-based Asymmetric Aminohydroxylation of Isopropyl rraAi.s-cinnamate. Tetrahedron Asymmetry 10 671... 

Propenoic acid, 3-[2,2-bis (1-methylethyl) phenyl]-, methyl ester. See Di isopropyl methyl cinnamate... 

A different pattern of reaction products was obtained with the ethyl 3 and isopropyl 5 cinnamic esters. In both cases, comparable chemical yields were obtained, but in addition to the 1,2-altemate (4a, 6a, respectively) and the flattened-cone (4b, 6b, respectively), a third type of stereoisomers (namely, 4c and 6c) emerged from the reaction mixture. An accurate analysis of H and NMR spectra pointed out the existence of two symmetry planes. DIF NOE experiments revealed the proximity of the methine and the methylene groups with the aromatic protons. Therefore, on the basis of only NMR evidences, 4c and 6c were assigned the 1,3-altemate conformation with the pseudoequatorial side chains in an all -cis position. Later, thanks to the obtainment of suitable crystals for X-ray analysis, the stereoisomer 4c was definitively reassigned the chair conformation [6]. 

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