On the Rearrangements of Biologically-Relevant Vinyl Allene Oxides to cis-Cyclopentenones, Ketols, Cyclopropylcarbinols and Favorskii-type Carboxylic Acids

2021 ◽  
Author(s):  
Pedro Villar ◽  
Alexander Grechkin ◽  
Adán B Gónzalez Pérez ◽  
Angel R. de LERA
Keyword(s):  
Carboxylic Acids ◽  
Biologically Relevant ◽  
Dft Computations ◽  
Naturally Occurring ◽  
Allene Oxides ◽  
Acetic Acids

In addition to stereodefined cis-cyclopentenones, the rearrangement of naturally-occurring vinyl allene oxides can provide ketols, cyclopropylcarbinols, and Favorskii-type bis-(Z)-but-2-en-1-yl acetic acids. These processes have been studied by DFT computations using...

Rearrangement of vinyl allene oxide geometric isomers to cyclopentenones. Further computational insights with biologically relevant model systems

2017 ◽  
Vol 15 (13) ◽  
pp. 2846-2855 ◽  
Author(s):  
Adán B. González-Pérez ◽  
Alexander Grechkin ◽  
Ángel R. de Lera
Keyword(s):  
Computational Study ◽  
Model Systems ◽  
Allene Oxide ◽  
Geometric Isomers ◽  
Relevant Model ◽  
Biologically Relevant ◽  
Biological Relevance ◽  
Naturally Occurring ◽  
Allene Oxides

A computational study of the rearrangement of vinyl allene oxides of biological relevance, which include alkyl (methyl, propyl) or unsaturated groups (allyl, crotyl) attached to the Csp3 atom has revealed interesting insights into the formation of naturally occurring cyclopentenones.

2,2-Dialkylacetic Acids -A New Class of Naturally Occurring Lipid Constituents

1995 ◽  
Vol 50 (1-2) ◽  
pp. 123-126 ◽  
Author(s):  
Gottfried Raab ◽  
Jürgen Jacob
Keyword(s):  
Retention Time ◽  
Relative Retention Time ◽  
Methyl Esters ◽  
South American ◽  
Time Data ◽  
New Class ◽  
The Past ◽  
Relative Retention ◽  
Naturally Occurring ◽  
Acetic Acids

Abstract The uropygial gland waxes of the South American red-legged Seriema (Cariama cristata (L., 1766)) were found to be composed of unbranched alcohols and 2,2′-dialkyl-substituted acetic acids which so far have not been found in skin lipids. When used as a chemosystematic character, the occurrence of this lipid class separates the order Cariamiformes (Seriemas) from all other avian orders hitherto investigated, especially from the Gruiformes (cranes and rails) to which they have been tentatively attributed in the past. From the GC retention time data now available for a series of 2-alkyl-substituted fatty acid methyl esters relative retention time indices for other compounds may be predicted.

ChemInform Abstract: Synthesis of 2-Methylchromone-8-acetic Acids and 2-Methylchromone-8-carboxylic Acids.

ChemInform ◽  
2010 ◽  
Vol 32 (44) ◽  
pp. no-no
Author(s):  
S. G. Jagadeesh ◽  
G. L. David Krupadanam ◽  
G. Srimannarayana
Keyword(s):  
Carboxylic Acids ◽  
Acetic Acids

scholarly journals Computational notes on the electronic properties of carboxylic acid

2020 ◽  
Vol 9 (2) ◽  
pp. 1079-1082
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Electronic Properties ◽  
Carboxylic Acids ◽  
Normal Mode ◽  
Normal Modes ◽  
Carboxyl Groups ◽  
Vibrational Characteristics ◽  
Vibrational Features ◽  
Acetic Acids

The present work describing the electronic properties and vibrational characteristics of carboxylic acids. Acetic acid is chosen as model molecules then optimized at B3LYP/6-31g(d,p) level of theory. The vibrational frequencies were calculated at the same level of theory. Band assignments which were calculated as 18 normal modes were assigned as one compare the normal mode coordinates with original one. Band assignments were described indicating the directions of normal modes in terms the vibrating atoms of the acetic acids. It could be concluded that DFT could be a useful tool for elucidation both the structural and vibrational features of carboxylic acids and then further utilized for assignment of the structures contains carboxyl groups which are known as most reactive structures in chemistry, biology and environment.

scholarly journals Importance of secondary sources in the atmospheric budgets of formic and acetic acids

2010 ◽  
Vol 10 (10) ◽  
pp. 24435-24497 ◽  
Author(s):  
F. Paulot ◽  
D. Wunch ◽  
J. D. Crounse ◽  
G. C. Toon ◽  
D. B. Millet ◽  
...  
Keyword(s):  
Formic Acid ◽  
Carboxylic Acids ◽  
Transport Model ◽  
Negative Temperature ◽  
Photochemical Oxidation ◽  
Secondary Source ◽  
Chemical Transport Model ◽  
Wet And Dry Deposition ◽  
Secondary Sources ◽  
Acetic Acids

Abstract. We present a detailed budget of formic and acetic acids, two of the most abundant trace gases in the atmosphere. Our bottom-up estimate of the global source of formic and acetic acids are ~1200 and ~1400 Gmol/yr, dominated by photochemical oxidation of biogenic volatile organic compounds, in particular isoprene. Their sinks are dominated by wet and dry deposition. We use the GEOS-Chem chemical transport model to evaluate this budget against an extensive suite of measurements from ground, ship and satellite-based Fourier transform spectrometers, as well as from several aircraft campaigns over North America. The model captures the seasonality of formic and acetic acids well but generally underestimates their concentration, particularly in the Northern midlatitudes. We infer that the source of both carboxylic acids may be up to 50% greater than our estimate and report evidence for a long-lived missing secondary source of carboxylic acids that may be associated with the aging of organic aerosols. Vertical profiles of formic acid in the upper troposphere support a negative temperature dependence of the reaction between formic acid and the hydroxyl radical as suggested by several theoretical studies.

scholarly journals Synthesis of Two Naturally Occurring 3-Methyl-2,5-dihydro-1-benzoxepin Carboxylic Acids

ChemInform ◽  
2006 ◽  
Vol 37 (6) ◽  
Author(s):  
Seiji Yamaguchi ◽  
Nao Tsuchida ◽  
Masahiro Miyazawa ◽  
Yoshiro Hirai
Keyword(s):  
Carboxylic Acids ◽  
Naturally Occurring

Studies related to naturally occurring acetylene compounds. XXXV. Investigation of Erigeron spp. from the Australian mountains and Tasmania

1969 ◽  
Vol 22 (4) ◽  
pp. 751 ◽  
Author(s):  
JS Sorensen ◽  
NA Sorensen
Keyword(s):  
Carboxylic Acids ◽  
Northern Hemisphere ◽  
Methyl Esters ◽  
Naturally Occurring ◽  
Acetylene Compounds ◽  
Acetylenic Compounds

Two Australian members of the genus Erigeron L. (Compositae, tribe Astereae) have been investigated with particular regard to their content of acetylenic compounds. E. conyzoides F. Muell. contained the methyl esters (I) and (II) of acetylenic carboxylic acids and their corresponding lactones (III) and (IV) and in this resemble the numerous Erigeron spp. of the northern hemisphere investigated earlier. Of the collective species E. pappochroma Labill. three Tasmanian and two Snowy Mountain collections were investigated. None of them contained the acetylenic compounds characteristic of typical Erigeron. Three of these collections contained some simple acetylenic alcohols, (V)-(IX); some of these are characteristic compounds of other genera of the tribus Astereae. In two collections acetylenic compounds were seemingly absent; but dill apiol (XI) was found in appreciable amounts.

Use of Ethyl (Benzothiazol-2-ylsulfonyl)acetate for Malonic Ester-type Syntheses of Carboxylic Acids and Esters

2014 ◽  
Vol 67 (9) ◽  
pp. 1222 ◽  
Author(s):  
Waleed M. Hussein ◽  
Ross P. McGeary
Keyword(s):  
Carboxylic Acids ◽  
Alkyl Halides ◽  
Malonic Ester ◽  
One Pot ◽  
Dichloromethane Solution ◽  
Mild Conditions ◽  
Acetic Acids

A new methodology for the synthesis of substituted carboxylic acids is described. Alkylation of either ethyl (benzothiazol-2-ylsulfonyl)acetate or ethyl 2-(benzothiazol-2-ylsulfonyl)propionate was achieved with alkyl halides and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane solution. These products were then desulfinated and hydrolysed in one-pot under mild conditions to give substituted acetic acids in good-to-excellent yields.

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