81246-46-0Relevant articles and documents
Stable isotope characterization of the ortho-oxygenated phenylpropanoids: Coumarin and melilotol
Brenna, Elisabetta,Fronza, Giovanni,Fuganti, Claudio,Gatti, Francesco G.,Grande, Valentina,Serra, Stefano,Guillou, Claude,Reniero, Fabiano,Serra, Francesca
, p. 9383 - 9388 (2005)
The natural abundance 2H NMR spectra of extractive coumarin 10 and of its dihydroderivative melilotol 11 produced by baker's yeast reduction has been compared with synthetic materials. Diagnostic for the differentiation of 10 are the (D/H)β values, which are in the 128.1-133.6 ppm interval for the natural compounds but 258.5 and 189.8 ppm for the synthetic materials. Such a dramatic difference is also found for methyl cinnamate 12, which shows (D/H)β values of 127.2 and 515.8 ppm, respectively. In extractive 10, the ratio (D/H)4(para)/(D/H)6(ortho) = 1.24 is similar to that observed in structurally related salicin and methyl salicylate. Coumarin 10 is transformed in salicyl alcohol 9, providing diacetate 14, showing in the natural series the trend (D/H)3(meta) > (D/H)4(para) > (D/H)5(meta) ~ (D/H) 6(ortho). A similar trend is shown also by the synthetic 10. A clear distinction between extractive and synthetic 10 is obtained through δ18O determinations on 10 and on chroman 13. The bulk δ18O values in the extractive series of 10 are 20.3, 23.6, and 22.6‰, while those of the aromatic oxygen are 2.3, 0.5, and -0.5‰. In the synthetic sample, the values are 12.6 and 5.6‰, respectively. As a final product, the reduction of 10 leads to the dihydroderivative 11. Both the baker's yeast reduction and the catalytic hydrogenation lead to a marked decrease of the deuterium content of 11, which is stronger for the β-position than for the α-position.
Quinuclidyl benzoxepins as 5-HT3 antagonists
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, (2008/06/13)
Certain specific substituted 9-N-(1-azabicyclo-[2.2.2.]octan-3-yl)carboxamido-2,3,4,5-tetrahydro-1-benzoxepins and their valuable use as 5-HT3 antagonists having CNS and gastric prokinetic acticity and void of any significant D2 receptor binding properties are disclosed. Methods for their preparation also are described.
Methylase Models: Studies on General-Base vs. Nucleophilic Catalysis in the Intramolecular Alkylation of Phenols
Knipe, Jay O.,Vasquez, Peter J.,Coward, James K.
, p. 3202 - 3209 (2007/10/02)
The ortho substituted phenols, 1 and 3, have been synthesized as models for the O-methylation of catecholamines, as catalyzed by catechol O-methyltransferase.The decomposition of 1 and 3 was studied at 40 deg C over a wide range of pH in both oxyanion and