42522-59-8Relevant academic research and scientific papers
Biosynthesis of the insect pheromone (S)-4-methyl-3-heptanone
Jarvis, Andrew P.,Liebig, Juergen,Hoelldobler, Bert,Oldham, Neil J.
, p. 1196 - 1197 (2004)
Using stable isotope-labelled probes and mass spectrometry, the insect pheromone (S)-4-methyl-3-heptanone is shown to be biosynthesised from three propionate units following a polyketide/fatty acid-type metabolic route.
A convenient and inexpensive synthesis of labelled methylmalonic and propionic acids: Application to the synthesis of methyl-d3-malonic and of propionic-3,3,3-d3 acids
Allevi, Pietro,Longo, Alessandra,Anastasia, Mario
, p. 1085 - 1091 (1999)
A synthetic route for obtaining highly pure methylmalonic and propionic acids labelled at the methyl groups is validated by the preparation of methyl-d3-malonic and propionic-3,3,3-d3 acids. The synthesis involves the alkylation of the diethyl allylmalonate with iodomethane-d3, deallylation of the resulting diethyl allylmethyl-d3-malonate by treatment with (η2-propene)Ti(O-i-Pr)2 and hydrolysis. Decarboxylation of the obtained methyl-d3-malonic acid affords propionic-3,3,3-d3 acid.
Effect of isotopic substitution on the electron spin dynamics of the CH3C(COOH)2 radical in X-irradiated methyl malonic acid powder: Intrinsic potentials and activation energies
Sornes,Benetis,Erickson,Mahgoub,Eberson,Lund
, p. 8987 - 8994 (1997)
The temperature-dependent EPR line shapes from the methyl rotor of the X irradiation-induced CH3C(COOH)2 radical in powder MMA (methyl malonic acid) and the X irradiation-induced radical CD3C(COOH)2 in methyl-specifically deuterated powder MMA are studied experimentally for the temperature range 4.8 K (5 K) to 77 K (65 K). The hydrogenated system is simulated using a quantum inertial dynamical model with a hindering potential and three-site exchange rotation. The deuterated system is simulated using a classical three-site exchange model. The results show that due to the increase in moment of inertia, the tunneling frequency is negligible for the deuterated rotor, resulting in a stopped rotor low-temperature spectrum, while being sufficiently large for the hydrogenated system for this to exhibit tunneling. From the low-temperature deuterated analogue spectrum, the potential twist angle is estimated to δ = ±50°±2° (+n·60°, n∈Z). The site-exchange activation energy of the deuterium rotor is observed to be 387 K, substantially lower than the hindering potential depth of 618 K. The hydrogenated system exchange rotation rate assumes a linear behavior with 754 K activation energy in the classical region of temperatures above 50 K.
A five deuterium generation jasmonic, its salt, wherein the intermediate, preparation method and use
-
Paragraph 0135; 0136, (2017/04/03)
The invention discloses an 11,11,12,12,12-pentadeuterojasmonic acid disclosed as Formula 11, a salt and intermediate, and a preparation method and application thereof. The preparation method of the pentadeuterojasmonic acid comprises the following steps:
High-valent palladium-promoted formal Wagner-Meerwein rearrangement
Wu, Hongmiao,Yang, Bin,Zhu, Lin,Lu, Ronghua,Li, Guigen,Lu, Hongjian
supporting information, p. 5804 - 5807 (2016/11/29)
An oxy-palladation, formal Wagner-Meerwein rearrangement and fluorination cascade has been established for generating fluorinated oxazolidine-2,4-diones and oxazolidin-2-ones. The reaction has a broad substrate scope in which both aryl and alkyl groups can be utilized as efficient migrating groups. Experimental evidence suggests that the reaction is initiated by anti-oxy-palladation of the olefin, followed by oxidative generation of an alkyl PdIV intermediate and a concerted migration-fluorination.
An improved procedure for the synthesis of labelled fatty acids utilizing diethyl malonate
Kasumov, Takhar,Brunengraber, Henri
, p. 171 - 176 (2007/10/03)
An improved procedure for the preparation and purification of labeled fatty acids by malonic ester synthesis has been developed. This method uses the different hydrolysis rates of the monoalkylmalonic ester intermediate and its dialkylmalonic ester side p
Pseudo One-Step Cleavage of C-C Bonds in the Decomposition of Ionized Carboxyclic Acids. Radical Like Reactions in Mass Spectrometry
Weiske, Thomas,Schwarz, Helmut
, p. 323 - 347 (2007/10/02)
Metastable molecular ions of hexanoic acid (1) decompose unimolecularly to C2H5. and protonated methacrylic acid (5-H+)(92percent rel. abund.).Investigation of the mechanism reveals that 1) the branched cation radical 11 must be regarded as the essential intermediate in the course of the rearrangement/dissociation reaction and 2) the process commences with intramolecular hydrogen transfer from either C-3 or C-5 to the ionized carbonyl oxygen ("hidden" hydrogen migration).Hydrogen transfer from C-4, which would correspond to the well-known McLafferty rearrangement, is of no importance in the C2H5.-elimination from 1.The same conclusion applies for various alternative mechanisms, as for example a SRi type reaction, 1 -> 2-H+.The gas phase chemistry of the cation radical of 1, and in particular the hydrogen exchange processes between the methylene groups C-2/C-3 and C-5/C-6, is in surprisingly close correspondence to the chemistry of free alkyl radicals. - The syntheses of various 13C and 2H-labelled model compounds are described.
