19136-97-1

Usage

Uses

Used in Research and Development:
HYDROCINNAMIC-2,2-D2 ACID is used as a research compound for various scientific applications. Its isotopically labeled nature allows researchers to study the behavior and properties of hydrocinnamic acid and its derivatives in a controlled manner, providing valuable insights into their chemical and biological interactions.
Used in Chemical Synthesis:
In the field of chemical synthesis, HYDROCINNAMIC-2,2-D2 ACID can be employed as a starting material or intermediate for the production of other isotopically labeled compounds. This can be particularly useful in the development of new drugs, agrochemicals, or other specialty chemicals that require the incorporation of deuterium for various reasons, such as improved stability or altered metabolic properties.
Used in Biochemical Studies:
HYDROCINNAMIC-2,2-D2 ACID can also be utilized in biochemical research to investigate the metabolic pathways and enzyme interactions involving hydrocinnamic acid and its derivatives. The presence of deuterium in the molecule can help researchers to differentiate between the labeled and unlabeled compounds, providing a valuable tool for studying enzyme mechanisms and metabolic processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, HYDROCINNAMIC-2,2-D2 ACID can be used as a building block for the development of isotopically labeled drug candidates. These labeled compounds can be used in preclinical and clinical studies to better understand the pharmacokinetics, pharmacodynamics, and metabolic profiles of the drug candidates, ultimately leading to the optimization of drug design and development.
Used in Analytical Chemistry:
HYDROCINNAMIC-2,2-D2 ACID can be employed as an internal standard or reference compound in various analytical techniques, such as mass spectrometry, nuclear magnetic resonance (NMR) spectroscopy, and chromatography. The presence of deuterium in the molecule can help to improve the accuracy and precision of these analytical methods, particularly when analyzing complex mixtures or trace amounts of hydrocinnamic acid and its derivatives.

Upstream product

• 103-25-3 3-phenylpropanoic acid methyl ester 
• 15785-29-2 1,1,-d²-2-phenylethyl bromide 
• 114-84-1 phenylpropionic acid sodium salt 
• 3709-27-1 5-benzyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 103-82-2 phenylacetic acid 
• 40638-92-4 1,1-dideuterio-2-phenylethanol 
• 124-38-9 carbon dioxide 
• 104-53-0 3-phenyl-propionaldehyde 
• 29372-33-6 α,α-dideuterated hydrocinnamaldehyde 
• 1186-52-3 tetradeuterioacetic acid 
• 100-39-0 benzyl bromide 

Downstream Products

• 17428-98-7 2-[D₂]-3-phenylpropan-1-ol 
• 60468-24-8 (2-deuterio-2-propenyl)benzene 
• 83026-03-3 C₁₅H₁₄⁽²⁾H₂Se 
• 83025-98-3 C₁₅H₁₄⁽²⁾H₂OSe 
• 83025-97-2 C₁₆H₁₆⁽²⁾H₂O₃S 
• 51086-43-2 2-[D₂]-4-phenylbutanoic acid 
• 61233-28-1 α,α-Dideutero-3-phenylpropionylchlorid 

Relevant academic research and scientific papers

Controllable Intramolecular Unactivated C(sp3)-H Amination and Oxygenation of Carbamates

Dual catalyst-controlled intramolecular unactivated C(sp3)-H amination and oxygenation of carbamates merging visible-light photocatalysis and earth-abundant transition metal catalysis have been reported. Useful amino alcohol and diol derivatives could be selectively obtained from readily available tertiary alcohol derivatives. The possible mechanisms have been proposed via a 1,5-HAT process followed by Lewis acid-controlled cyclization. The nickel and zinc catalysts inhibit the formation of oxygenation and amination products, respectively. An interesting phenomenon of chirality transfer is also observed.

Palladium(II)-Catalyzed Enantioselective Arylation of Unbiased Methylene C(sp3)?H Bonds Enabled by a 2-Pyridinylisopropyl Auxiliary and Chiral Phosphoric Acids

Enantioselective functionalizations of unbiased methylene C(sp3)?H bonds of linear systems by metal insertion are intrinsically challenging and remain a largely unsolved problem. Herein, we report a palladium(II)-catalyzed enantioselective arylation of unbiased methylene β-C(sp3)?H bonds enabled by the combination of a strongly coordinating bidentate PIP auxiliary with a monodentate chiral phosphoric acid (CPA). The synergistic effect between the PIP auxiliary and the non-C2-symmetric CPA is crucial for effective stereocontrol. A broad range of aliphatic carboxylic acids and aryl bromides can be used, providing β-arylated aliphatic carboxylic acid derivatives in high yields (up to 96 %) with good enantioselectivities (up to 95:5 e.r.). Notably, this reaction also represents the first palladium(II)-catalyzed enantioselective C?H activation with less reactive and cost-effective aryl bromides as the arylating reagents. Mechanistic studies suggest that a single CPA is involved in the stereodetermining C?H palladation step.

Triazolium Carbene Catalysts and Stereoselective Bond Forming Reactions Thereof

Provided herein are triazolium carbine catalysts useful for asymmetric hydration, fluorination, and deuteration, and processes for their preparation. Also provided are synthetic reactions in which these catalysts are used, in particular, in stereoselective formation of carbon-chlorine, carbon-hydrogen, carbon-fluorine, and carbon-deuterium bonds.

Diagnostic fragmentations of adducts formed between carbanions and carbon disulfide in the gas phase. A joint experimental and theoretical study

Selected carbanions react with carbon disulfide in a modified LCQ ion trap mass spectrometer to form adducts, which when collisionally activated, decompose by processes which in some cases identify the structures of the original carbanions. For example (i) C6H5- + CS 2→ C6H5CS2-→ C6H5S- + CS, occurs through a 3-membered ring ipso transition state, and (ii) the reaction between C6H 5CH2- and CS2 gives an adduct which loses H2S, whereas the adduct(s) formed between o-CH 3C6H5- and CS2 loses H2S and CS. Finally, it is shown that decarboxylation of C 6H5CH2CH2CO2- produces the β-phenylethyl anion (PhCH2CH2 -), and that this thermalized anion reacts with CS2 to form C6H5CH2CH2CS2 - which when energized fragments specifically by the process C 6H5CH2CH2CS2 -→ C6H5CH2-CHC(S)SH → [(C6H5CH2CHCS) -SH] → C6H5CH2CCS- + H2S. Experimental findings of processes (ii) and (iii) were aided by deuterium labelling studies, and all reaction profiles were studied by theoretical calculations at the UCCSD(T)/6-31+G(d,p)//B3LYP/6-31+G(d,p) level of theory unless indicated to the contrary.

Isomerisation reaction of a gem-bis-trifluoromethyl olefin in a basic medium: A kinetic study

The rearrangement of 5-phenyl-1,1,1-trifluoro-2-(trifluoromethyl)pent-2-ene to 5-phenyl-1,1,1-trifluoro-2-(trifluoromethyl)pent-3-ene has been studied by 19F NMR in dimethylsulphoxide (DMSO). This isomerisation is catalysed by a base such as tr

Synthesis of deuterium labelled acids

Knoevenagel condensation of Meldrum's acid (1) with benzaldehyde, anisaldehyde, furfural, cinnamaldehyde and acetone gave the corresponding alkylidene derivatives (3) which were reduced with sodium borohydride to yield alkyl Meldrum's acids (4). Reaction

A NEW MECHANISM FOR THE PHOTOCLEAVAGE OF MONOTHIOIMIDES

Based on solid state structure-reactivity correlation studies and on deuterium labeling experiments, it is concluded that the photochemical formation of thiobenzanilides 2a-d from monothioimides 1a-d does not involve initial γ-hydrogen atom abstraction as originally suggested in the literature.Alternative mechanistic possibilities are presented and discussed.

On the Generation and Characterization of the Spirooctadienyl Anion in the Gas Phase

Three routes have been explored in both a high-pressure chemical ionization (CI) source and a low-pressure Fourier transform ion cyclotron resonance (FT-ICR) cell to generate the spirooctadienyl anion in the gas phase: (i) proton abstraction from spiroocta-4,6-diene; (ii) expulsion of trimethylsilyl fluoride by phenyl ring participation following fluoride anion attack upon the silicon centre of 2-phenylethyl trimethylsilane; and (iii) collisionally induced dissociation (CID) of the carboxylate anion of 3-phenylpropanoic acid via carbon dioxide loss.From comparison of the CID spectra of various reference (1-) ions with those of the (1-) ions with those of the (1-) ions which could be generated via the routes (i) and (iii) in the CI source it can be concluded that only the third route yields a (1-) in whose CID spectrum is not inconsistent with the one expected for the spirooctadienyl anion.In the FT-ICR cell (1-) ions are generated along all three routes; their structures have been identified by specific ion-molecule reactions and appear to be different.Route (i) yields an α-methyl benzyl anion, probably due to isomerization within the ion-molecule complex formed.An ortho-ethylphenyl anions is formed along route (ii), presumably due to an intramolecular ortho proton abstraction in the generated trimethylsilyl fluoride solvated 2-phenylethyl primary carbanion.The (1-) ion formed along route (iii) shows reactions similar to those of the 1,1-dimethylcyclohexadienyl anion which is structurally related to the spirooctadienyl anion.Furthermore, the (1-) ion generated via route (iii) reacts with hexafluorobenzene under expulsion of only one hydrogen fluoride molecule which contains exclusively one of the original phenyl ring hydrogen atoms.On the basis of all these observations it is therefore quite likely that the spirooctadienyl anion is formed by collisionally induced decarboxylation of the 3-phenylpropanoic acid carboxylate anion and can be a long-lived and stable species in the gas phase.

Mechanistic Features of Allylic Hydrogen Abstraction by Alkoxy Radicals

A TS(excit) of angular H abstraction from allylbenzene in the course of the allylic acetoxylation reaction was previously invoked to explain a temperature-independent primary KIE; kH/kD = 2.90.This reaction geometry is now fully supported by the finding of inverse α-secondary deuterium isotope effects at both ends of the double bond in allylbenzene; (kH/kD)αC1 = 0.977 and (kH/kD)αC2 = 0.985.In keeping with these results an unsymmetrically structured, bridged radical intermediate, formed by the interaction of t-BuO with the allylic double bond, steers the reaction course.Such a complex is recognized to be unusual since most of the verified cases of radical bridging involve heteroatom centers capable of octet expansion.A discussion is also given of the factors determining the relative influence of benzene and double bond participation in the H-abstraction reactions of allylbenzene, which possesses both of these activating functions.