ChemInform Abstract: CHEMISTRY OF ENOL ETHERS. LVI. STUDY OF THE CONDENSATION OF ACETALS OF AROMATIC ALDEHYDES WITH 1‐ETHOXY‐1,3‐BUTADIENE. SYNTHESIS OF ARYLPOLYENE ALDEHYDES

Makin, S. M.; Shavrygina, O. A.; Dobretsova, E. K.; Ermakova, G. A.; Dymshakova, G. M.

doi:10.1002/chin.198232145

Cited by 2 publications

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“…Eine Lsg. von 6c (18,2 g (94 mrnol)) in CCI, (650 ml (4,05), 303 (sh, 4,15), 335 (4,31). IR (KBr): 3080, 3040,3005,2965, 2840, 2730, 1670, 1600, 1515, 1423, 1400, 1275, 1225, 1165, 1130, 1015: 3,93, 3,94(jes, 2 MeO); 6,61 (dd, 3J = 15,8,7,7,CH (2)); 6,91 (d, 3J = 8,3, CH(5')); 7,08 (d, 4J = 2,0, CH (2)); 7,17 (dd, ' J = 8,3.…”

Section: Me0mentioning

confidence: 99%

“…IR (KBr): 3080, 3040,3005,2965, 2840, 2730, 1670, 1600, 1515, 1423, 1400, 1275, 1225, 1165, 1130, 1015: 3,93, 3,94(jes, 2 MeO); 6,61 (dd, 3J = 15,8,7,7,CH (2)); 6,91 (d, 3J = 8,3, CH(5')); 7,08 (d, 4J = 2,0, CH (2)); 7,17 (dd, ' J = 8,3. 4J = 2.0, CH (6) (20), 91 (25), 77 (30) (4,51). IR (KBr): 3030,3000, 2975, 2940,2920,2840, 2820,2750,2720,2675, 1615, 1515, 1425, 1270, 1140, 1020: 3,92, 3,94 (je s, 2 MeO); 6,25 (dd, 3J = 15,1, 8,0, CH (2)); 6,16 (m,CH(4), CH (5), CH(2), CH(5'), CH(6')); 7,26 (ddd, ' J = 15.1,9,3,4J = 0,9,CH(3)); 9,60 (d, ' -(3',4'-Dimethoxyphenylj-l,3,3-triethuxypropun (1 1) isoliert.…”

Section: Me0mentioning

confidence: 99%

“…IR (KBr): 3030,3000, 2975, 2940,2920,2840, 2820,2750,2720,2675, 1615, 1515, 1425, 1270, 1140, 1020: 3,92, 3,94 (je s, 2 MeO); 6,25 (dd, 3J = 15,1, 8,0, CH (2)); 6,16 (m,CH(4), CH (5), CH(2), CH(5'), CH(6')); 7,26 (ddd, ' J = 15.1,9,3,4J = 0,9,CH(3)); 9,60 (d, ' -(3',4'-Dimethoxyphenylj-l,3,3-triethuxypropun (1 1) isoliert. Die gesamte Menge (2,s mmol) wurde nach [4] mit AcOH zu 402 mg (74%) orangem Festkorper (6d/10) umgesetzt. Der Anteil von 10 liess sich durch 2maI Umkristallisieren aus EtOH von 5 auf I % (nach GC) senken, wobei auch die Ausbeute an 6d auf 200 mg (37 %) abnahm.…”

Section: Me0unclassified

“…Der Anteil von 10 liess sich durch 2maI Umkristallisieren aus EtOH von 5 auf I % (nach GC) senken, wobei auch die Ausbeute an 6d auf 200 mg (37 %) abnahm. ( (4,20), 292 (sh, 331). IR (Film): 3560-3300 (br.…”

Section: Me0unclassified

“…73,9-753". UVjVIS (MeOH): 256 (3,97), 264 (sh 3,95), 356 (4,47). IR (KBr): 3070, 3025, 3000, 2950, 2935, 1680, 1585, 1445, 1425, 1370, 1365, 1270, 1250, 1140, 1075, 1025, 1010: 0,90 (t, 3J = 6,5, CH,(lO)); 1,20-1,45 (m, CH2(8), CH2 (9)); 1,55-1,75 (m, CH2 (7)); 2,58 (t, 3J = 7,4, CH, (6) (12).…”

Section: Me0mentioning

confidence: 99%

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Synthese von Alkylphenolen und ‐pyrocatecholen aus Plectranthus albidus (Labiatae)

Bürgi

Liu

Rüedi

1993

Helvetica Chimica Acta

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In the preceding paper, we described the isolation and structure elucidation of a series of even-numbered phenol-or pyrocatechol-derived 1 -arylalkane-5-ones. To establish the assigned structures unambiguously and to have larger quantities available for physiological testing, the following compounds were prepared: in the alkylphenol series, 1-(4-hydroxyphenyl)tetradecan-5-one (2a), 1-(4-hydroxyphenyl)hexadecan-5-one (2b), and 1-(4hydroxyphenyl)octadecan-5-one (2c); in the alkylcatechol series, 1 -(3',4-dihydroxyphenyl)decan-5-one (3a; not isolated as a natural compound), 1-(3',4-dihydroxyphenyl)dodecan-5-one (3b), 1-(3',4'-dihydroxyphenyl)tetradecan-5-one (3c), 1-(3',4'-dihydroxyphenyl)hexadecan-5-one (3d), I-(3',4-dihydroxyphenyl)octadecan-5-one (3e), and 1-(3',4-dihydroxyphenyl)icosan-S-one (30 ; in the alkenylphenol series, (2)-1-(4-hydroxyphenyI)octadec-l3en-5-one (4a) and (E)-l-(4-hydroxyphenyl)octadec-13-en-5-one (4b); in the alkenylcatechol series, (E,E)-l-(3',4'-dihydroxypheny1)deca-1,3-dien-S-one (1) and ( Z ) -1-(3',4'-dihydroxyphenyl)octadec-13-en-5-one (5). All compounds proved to be identical with the previously assigned structures. Compound 1 was synthesized by regioselective aldol condensation of heptan-2-one with (E)l-(3',4'-dimethoxyphenyl)prop-2-enal(6d; Scheme I ) , the phenols 2a+ and the catechols 3a-f by addition of the corresponding alkyl Grignard reagent to 5-(4'-methoxypheny1)or 5-(3',4'-dimethoxyphenyl)pentanal(17~ and 18c, resp.; Scheme 4 ) , and the olefins 4a, 4b and 5 from 17c or 18c oia the 9-0 -silyl-protected 13-(4'-methoxyphenyl)-or 13-(3',4'-dimethoxyphenyl)tridecanals (26 and 27, resp.) and Wittig olefination as the key steps (Scheme 5 ) .

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Section: Me0mentioning

confidence: 99%

Section: Me0mentioning

confidence: 99%

Section: Me0unclassified

Section: Me0mentioning

confidence: 99%

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Synthese von Alkylphenolen und ‐pyrocatecholen aus Plectranthus albidus (Labiatae)

Bürgi

Liu

Rüedi

1993

Helvetica Chimica Acta

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[n]-Polyenovanillins (n = 1−6) as New Push−Pull Polyenes for Nonlinear Optics: Synthesis, Structural Studies, and Experimental and Theoretical Investigation of Their Spectroscopic Properties, Electronic Structures, and Quadratic Hyperpolarizabilities

et al. 1996

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We describe the synthesis and quadratic hyperpolarizability properties of [n]-polyenovanillins, a new family of push−pull polyenes deriving from vanillin, thiovanillin, and isothiovanillin. Twenty-five [n]-polyenovanillins of structure 3,4-(RO;R‘S)C6H4(CHCH) n CHO [with n = 1−6 and R, R‘ = Me or n-Bu] were synthesized by using a Wittig−Horner polyvinylogation methodology, and the structure of one of these was established by single-crystal X-ray crystallography. The UV−vis absorption and fluorescence spectra of these polyenovanillins were recorded and interpreted in light of CNDO/S calculations that allowed the identification of the different transitions. EFISH measurements provided up to 350 × 10-30 esu (for 14, n = 6) with an exponential increase of the quadratic hyperpolarizability with the conjugation length. These data were satisfactorily interpreted by means of a CNDO/S/NLO method which provided information as to the relative orientation of the dipole moment μ and βvec, the vector part of the hyperpolarizability tensor. In the sulfur-substituted series, there is a significant divergence between the orientation of μ and βvec, which in turn leads to an underestimation of β in the EFISH method. The calculation also revealed that when the length of the polyenic chain increases, the charge transfer from the donor toward the acceptor actually tends to concentrate on the polyenic chain rather than on the aldehyde group.

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ChemInform Abstract: CHEMISTRY OF ENOL ETHERS. LVI. STUDY OF THE CONDENSATION OF ACETALS OF AROMATIC ALDEHYDES WITH 1‐ETHOXY‐1,3‐BUTADIENE. SYNTHESIS OF ARYLPOLYENE ALDEHYDES

Abstract: Veratrumaldehyd (I) wird in das Diethylacetal (II) übergeführt, das mit Vinylethylether zu dem Addukt (III) und mit dem Dien (IV) zu dem 1:1‐Addukt (VIa) und dem l:2‐Addukt (VIIa) reagiert, wobei das Mengenverhältnis (VIa)/(VIIa) vom Mengenverhältnis Acetal/Dien abhängt.

Cited by 2 publications

References 0 publications

Synthese von Alkylphenolen und ‐pyrocatecholen aus Plectranthus albidus (Labiatae)

Synthese von Alkylphenolen und ‐pyrocatecholen aus Plectranthus albidus (Labiatae)

[n]-Polyenovanillins (n = 1−6) as New Push−Pull Polyenes for Nonlinear Optics: Synthesis, Structural Studies, and Experimental and Theoretical Investigation of Their Spectroscopic Properties, Electronic Structures, and Quadratic Hyperpolarizabilities

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