Trans-3- propenoic

The addition of a-(acylamino) esters to 3-aryl-2-propenoates, with sodium ethoxide in ethanol or sodium hydride in benzene as base, is a frequently ultilized procedure9-" A The initial Michael adducts cyclize to 3-aryl-5-oxo-2-pyrrolidinecarboxylic acids with modest to high trans diastereoselectivities 10°. [Pg.964]

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. [Pg.965]

FIGURE 2.18 Partial deuteriumation of ds-3-phenyl propenoic acids showing the fraction of deuterium in olefinic positions of recovered trans isomers. Numbers in parentheses are over Lindlar catalyst.121... [Pg.53]

A new dipolarophile bearing a chirality-controlling heterocyclic auxiliary at the p-position is readily accessible from (5)-A -benzylvalinol and methyl ( )-4-oxo-2-propenoate. However, the dipolarophile is available only as an 86 14 equilibrium mixture of trans and cis stereoisomers (Scheme 11.20) (84). When this is used without separation in the reaction with the Al-hthiated azomethine ylide derived from methyl (benzylideneamino)acetate in THE at 78 °C for 3.5 h, a mixture of two diastereomeric cycloadducts (75 25) was obtained in 82% yield. These two cycloadducts are derived from the trans and cis isomers of acceptor, indicating that both cycloadditions were highly diastereoselective. [Pg.772]

AH26 c6h7no2 ethyl trans-3-cyano- propenoate NC1U1V02 CsH5OOCCH CHCN DMF PY Et4NCl04 0.1 H20 1 - - - DME/SCE --0 C=l,t=4.20, m=1.58... [Pg.224]

Ethyl-4-cyanopyridinium perchlorate, AM94 Ethyl diazoacetate, AC8l Ethyl diazoethanoate, AC8l Ethyl trans-3-(N,N-dimethyl-carbamyl)propenoate, A011 Ethylenediamine, ABIO Ethylenediaminetetraacetic acid,... [Pg.631]

Ethyl trans-3-trifluoromethyl-propenoate, AH14 Ethyl 4,4,4-trifluoro-3 (tri-fluoromethyl)crotonate, AJ67... [Pg.631]

Phenyl propena 1, APOO N-Phenylpropenamide, AP08 trans-3-Phenyl propenoic acid, AP02... [Pg.640]

Korhonen has also studied the El-induced fragmentation of a series of chlorinated methyl propenoates, comprising cis and trans isomers of all the mono-, di- and tri-chloro derivatives, and their trideuteromethyl derivatives211. One aspect which was examined in detail concerns the effect of the position of chlorine substituents on the isomerization of the substrate molecular ion, as depicted in Scheme 29 for 2-chloropropenoate. This isomerization, which had already been observed212, is revealed by the formation of [M - H20]+ and [M - C02H]+ ions typical of acids. This rearrangement is particularly favored for 2-chloropropenoate, but also takes place, although to a lesser extent, for cis-3-chloro- and... [Pg.229]

The intramolecular Diels-Alder reactions involving boryl-3-propenoic acid derivatives has been addressed to. So, heating the trienylamide (7) at 80°C in toluene for 15 hours led to a 1/3 mixture of the cycloadducts (8) and (8 ) isolated in 72 % yield (figure 6) l7. The trienylamide (9) could not be isolated since the IMDA occured at the temperature of the coupling step, i,e below 0°C in ether for 30 minutes. This very fast cyclisation led to a 85/15 mixture of cycloadducts (10) and (10 ) having respectively a cis and trans junction in the bicyclic structure. The cis bicyclic structure (10) results from an endo approach of the diene and the dienophile. This is in agreement with literature data l8. [Pg.467]

SYNS BENZYL ALCOHOL CINNAMIC ESTER BENZYL y-PHENYLACRYLATE Q CINNAMEIN trans-CINNAMIC ACID BENZYL ESTER FEMA No. 2142 3-PHENYL-2-PROPENOIC ACID PHENYLMETHYL ESTER (9CI)... [Pg.153]

C2H604S dimethyl sulfate 77-78-1 -32.00 1.6271 2 1409 C3H3CI02 trans-3-chloro-2-propenoic acid 2345-61-1 25.00 T3222 2... [Pg.210]

C9H7N04 trans-3-(2 nitrophenyl)-2 propenoic acid 1013-96-3 25.00 1.3674 2 16224 C9H803 m-hydroxycinnamic acid, predominantly trans 14755-02-3 25.00 1.2467 2... [Pg.243]

C10H9NO4 methyl trans-3-(2-nitrophenyl)-2-propenoate 39228-29-0 25.00 1.3140 2 19123 C10H1002 alpha-methyl-beta-oxobenzenepropanal 16837-43-7 27.69 1.0799 2... [Pg.250]

C10H9NO4 methyl trans-3-(4-nitrophenyl)-2-propenoate 637-57-0 25.00 1.3140 2 19125 C10H10O2 1-phenyl-1,3-butanedione 93-91-4 74.00 1.0599 1... [Pg.250]

C13H804 7,2-dihydroxy-1 H-benz[f]indene-1,3(2H)-dione 38627-57-5 25.00 1.3336 2 25629 C13H10O2 trans-3-(1-naphthyl)-2-propenoic acid 2006-14-6 23.00 1.1016 2... [Pg.264]

C10H9F3O 3-(trifluoromethyl)phenylacetone 21906-39-8 489.15 42.843 2 18931 C10H9NO4 methyl trans-3-(3-nitrophenyl)-2-propenoate 659-04-1 556.65 49.353 2... [Pg.490]

Synonyms ( )-3-Phenyl-2-propenoic acid trans-3-Phenylacrylic acid... [Pg.245]

Carboxylic acids that contain a double bond in their structure are called unsaturated carboxylic acids. Examples of these acids are propenoic acid, 2-methylpropenoic acid, trans-2-butenoic acid, cis-2-butenoic acid. [Pg.130]

A high preference for tra/w-substituted cyclopropanes is observed in the reaction of the sulfur ylide ethyl (dimethylsulfuranylidene)acetate with Michael acceptors34. Thus, the reaction with ethyl propenoate provides diethyl 1,2-cyclopropanedicarboxylate almost exclusively with trans stereochemistry. [Pg.1023]

Benzyl Cinnamate. 3-Phenyl-2-propenoic acid pbtnylmelhyl ester trans-cinnamic acid benzyl ester cinna-mein. CjjH tO, mol wt 238.27. C 80.65%, H 5.92%, O 13.43%. C(H5CH—CHOOOCHjCjHj. Constituent of sto-rax, Peru and Tolu balsams Tsehirch, Trog, Arch. Pharm. 232, 70 (1894) Tsehirch, Oberlander. ibid. 559. Prepn Volwiler, Vlict, J. Am. Chem. Soc. 43, 1672 (1921) Elicl. Anderson, ibid. 74, 547 (1952) Bender. Zerner, ibid. 84, 2550 (1962). [Pg.177]

Beilstein Handbook Reference) AI3-00949 Alkohol skoricovy BRN 1903999 CCRIS 3191 Cinnamic alcohol Cinnamyl alcohol EINECS 203-212-3 FEMA No. 2294 3-Fenyl-2-propen-1-ol HSDB 5011 NSC 8775 Peruvin 3-Phenylallyl alcohol o-Phenylallyl alcohol Phenyl-2-propen-1-ol 1-Phenylprop-1-en-3-ol 3-Phenyl-2-propen-1-ol 3-Phenyl-2-propenol 2-Propen-1-ol, 3-phenyl- 2-Propen-yl-ol, 3-phenyl- Propenoic xid, 3-phenyl-, (trans)- Styrone Styryl alcohol Styryl carbinol Zimtalcohol. Used in perfumery and in deodorants. Crystals mp = 33-35° bp 249-250° dJJ = 1.0397 soluble in H2O, organic solvents. [Pg.148]

Propenoic acid, 3-(3,4-dihydroxyphenyl)-, trans- trans-CAfieic acid ... [Pg.501]

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