The Synthesis of Some 1-Cyclopentenealdehydes

English, James; Barber, George W.

doi:10.1021/ja01178a011

Cited by 29 publications

(12 citation statements)

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“…908/5 · 10 À1 mbar. 1 (14), 119 (14), 91 (32), 79 (6), 77 (8), 65 (9), 55 (4), 51 (5), 39 (7), 29 (5), 27 (6).…”

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“…13 C-NMR: 15.5 (q); 28.0 (t); 75.5 (t); 75.8 (t); 120.0 (d); 120.7 (d); 123.1 (d); 140.3 (s); 146.2 (s); 148.1 (s); 204.8 (s). MS: 192 (100, M þ ), 177 (29), 150 (12), 149 (88), 136 (6), 135 (20), 123 (9), 122 (6), 121 (7), 108 (16), 105 (9), 94 (5), 91 (18), 89 (7), 80 (15), 79 (32), 78 (8), 77 (29), 67 (5), 65 (13), 63 (11), 55 (6), 51 (18), 39 (13), 27 (7).…”

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“…Benzene-1,2-diol (12a), 4-methylbenzene-1,2-diol (12b), 3methylbenzene-1,2-diol (12c), 4-ethylbenzene-1,2-diol (12f), 4-(tert-butyl)benzene-1,2-diol (12k), 4-(1,1dimethylpropyl)benzene-1,2-diol (12o), 2,3-dihydro-1H-indene-5,6-diol (12r), and naphthalene-2,3-diol (12s) were purchased from commercial sources. Several other catechols were synthesized as described in the literature: 3-isopropylbenzene-1,2-diol (12j), 4-isopropylbenzene-1,2-diol (12i) and 3,5-diisopropylbenzene-1,2-diol (12t)[14], 3-propylbenzene-1,2-diol (12h)[32], 4-propylbenzene-1,2-diol (12g)[33], 3,6-dimethylbenzene-1,2-diol (12e)[34].…”

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Structure–Activity Relationship in the Domain of Odorants Having Marine Notes

Gaudin

Nikolaenko

Laumer

et al. 2007

Helvetica Chimica Acta

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We synthesized or re-synthesized a large series of 2H-1,5-benzodioxepin-3(4H)-ones 9 (Scheme 1), 4,5-dihydro-1-benzoxepin-3(2H)-ones 10 (Schemes 3 and 4) and 5,6,8,9-tetrahydro-7H-benzocyclohepten-7-ones 11 (Schemes 5 and 6), since the lead compound for the olfactory note of perfumes based on marine accords is a well-known benzodioxepinone named Calone 1951 (9b). We meticulously described the odor profile of each synthesized compound and discussed relevant structure -odor relationships (Tables 1 -3). In particular, we revealed a correlation between the conformation of the seven-membered ring and the activities of these compounds (Table 4 and Fig. 3). We also clarified the effect of the position and the size of the alkyl substituent at the aromatic ring.

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“…908/5 · 10 À1 mbar. 1 (14), 119 (14), 91 (32), 79 (6), 77 (8), 65 (9), 55 (4), 51 (5), 39 (7), 29 (5), 27 (6).…”

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Structure–Activity Relationship in the Domain of Odorants Having Marine Notes

Gaudin

Nikolaenko

Laumer

et al. 2007

Helvetica Chimica Acta

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“…S9 †). [49][50][51] To ascertain this finding, the enzymes WT 4-OT and 4-OT F50A (1.0 mol% compared to 11) were incubated separately with 11 (15.4 mM in 20 mM NaD 2 PO 4 , pD = 7.6) and reaction progress was followed by 1 H NMR spectroscopy (Fig. S10 †).…”

Section: Organic and Biomolecular Chemistry Papermentioning

confidence: 99%

Inter- and intramolecular aldol reactions promiscuously catalyzed by a proline-based tautomerase

et al. 2017

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The enzyme 4-oxalocrotonate tautomerase (4-OT), which in nature catalyzes a tautomerization step as part of a catabolic pathway for aromatic hydrocarbons, was found to promiscuously catalyze different types of aldol reactions. These include the self-condensation of propanal, the cross-coupling of propanal and benzaldehyde, the cross-coupling of propanal and pyruvate, and the intramolecular cyclizations of hexanedial and heptanedial. Mutation of the catalytic amino-terminal proline (P1A) greatly reduces 4-OT's aldolase activities, whereas mutation of another active site residue (F50A) strongly enhances 4-OT's aldolase activities, indicating that aldolization is an active site process. This catalytic promiscuity of 4-OT could be exploited as starting point to create tailor-made, artificial aldolases for challenging self- and cross-aldolizations.

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“…Typically catalytic transformations are carried out at high pressures and high reaction temperatures with homogeneous or heterogeneous Pd-, Pt-, Ni,-Co-, Rh or Ru catalysts. [6][7][8][9][10][11][12][13][14][15][16][17][18] More recently, the hydrogenation of arenes using Rh and Ru nanoparticles as catalysts or using aqueous colloidal suspensions of catalytically active iridium(0)-species under ultrasonic irradiation have been investigated extensively. [19][20][21][22] Furthermore, phenols can be hydrogenated using samarium diiodide (SmI 2 ) as reductant.…”

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