4303-49-5

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl Malonate-d2 is used as an intermediate in the synthesis of various pharmaceutical compounds, including barbiturates, due to its unique deuterium-labeled structure. The incorporation of deuterium atoms can improve the stability and pharmacokinetic properties of the final products, leading to enhanced therapeutic effects and reduced side effects.
Used in Flavor and Fragrance Industry:
Diethyl Malonate-d2 is utilized as a building block for the creation of artificial flavorings and perfumes. Its deuterium-labeled nature allows for improved stability and longevity of the final products, ensuring a consistent and long-lasting sensory experience for consumers.
Used in Vitamin Production:
Diethyl Malonate-d2 serves as a key component in the production of essential vitamins, such as vitamin B1 and vitamin B6. The deuterium-labeled analog can enhance the stability and bioavailability of these vitamins, potentially improving their efficacy and absorption in the human body.

Upstream product

• 105-53-3 diethyl malonate 
• 7152-42-3 10-phenyl-10H-phenothiazine 

Downstream Products

• 38645-14-6 <2,2-2H2>propane-1,3-diol 
• 592-41-6 1-hexene 
• 110-54-3 hexane 
• 110-82-7 cyclohexane 
• 592-42-7 1,5-Hexadien 
• 544-10-5 1-Chlorohexane 
• 928-89-2 6-chlorohexene 
• 3922-28-9 1,12-dichlorododecane 
• 6414-58-0 diethyl 2-phenylaminomalonate 
• 284474-77-7 [1,1,2,2,3,3‐D₆]‐propanediol 

Relevant academic research and scientific papers

Preparation of Deuterium Labeled Compounds by Pd/C-Al-D2O Facilitated Selective H-D Exchange Reactions

The chemo/regioselective H-D exchange of amino acids and synthetic building blocks by an environmentally benign Pd/C-Al-D2O catalytic system is described. Due to the importance of isotope labeled compounds in medicinal chemistry and structural biology, no

Continuous-flow electro-oxidative coupling of sulfides with activated methylene compounds leading to sulfur ylides

An unprecedentedly straightforward electro-oxidative coupling of sulfides with activated methylene compounds to synthesize sulfur ylides has been developed. Good to excellent yields can be obtained under catalyst- and oxidant-free conditions at room tempe

Synthesis of a Series of Structurally Diverse MB327 Derivatives and Their Affinity Characterization at the Nicotinic Acetylcholine Receptor

A novel series of 30 symmetric bispyridinium and related N-heteroaromatic bisquaternary salts with a propane-1,3-diyl linker was synthesized and characterized for their binding affinity at the MB327 binding site of nicotinic acetylcholine receptor (nAChR) from Torpedo californica. Compounds targeting this binding site are of particular interest for research into new antidotes against organophosphate poisoning, as therapeutically active 4-tert-butyl-substituted bispyridinium salt MB327 was previously identified as a nAChR re-sensitizer. Efficient access to the target compounds was provided by newly developed methods enabling N-alkylation of sterically hindered or electronically deactivated heterocycles exhibiting a wide variety of functional groups. Determination of binding affinities toward the MB327 binding site at the nAChR, using a recently developed mass spectrometry (MS)-based Binding Assay, revealed that several compounds reached affinities similar to that of MB327 (pKi=4.73±0.03). Notably, the newly prepared lipophilic 4-tert-butyl-3-phenyl-substituted bispyridinium salt PTM0022 (3 h) was found to have significantly higher binding affinity, with a pKi value of 5.16±0.07, thus representing considerable progress toward the development of more potent nAChR re-sensitizers.

Synthesis of deuterated mevalonolactone isotopomers

A synthetic route was developed for the preparation of deuterated mevalonolactones. Using low-cost deuterated reagents, this route allows for the independent introduction of deuterium labeling into any carbon position or into any combination of positions. Following this approach, the synthesis of [6,6,6-2H3]mevalonolactone, [4,4,6,6,6-2H 5]mevalonolact-one, [5,5-2H2]mevalonolactone, [5,5,6,6,6-2H5]mevalonolact-one, and [2,2,6,6,6- 2H5]mevalonolactone is described.

Catalytic Mannich-type reactions of Sulfonylimidates

A novel nucleophile, sulfonylimidate, has been successfully employed in Mannich-type reactions. Due to electronwithdrawing property of sulfonyl group of sulfonylimidate, the acidity of α-proton is enhanced so that sulfonylimidate bearing no activating functional group at α-position is deprotonated by relatively weak base. DBU-catalyzed reactions of sulfonylimidates with protected imines in DMF provided the adducts in high yields with high anti selectivity. This reaction represents a wide substrate scope and a high catalytic turnover. A thorough kinetic study revealed that ratedetermining step is most likely deprotonation step in case of Ts-imidate. Alkali earth metal alkoxide and its HMDS salt also catalyze Mannich-type reactions of sulfonylimidates. The reactions catalyzed by Mg(O tBu)2 in DMF provided the adducts with high anti selectivity, while those catalyzed by [Sr(HMDS)2]2 gave syn selectivity. The asymmetric variant of Mannich-type reaction of sulfonylimidate was also achieved. Several transformations of sulfonylimidates to other functional groups were also demonstrated. Finally, direct-type catalytic formation of cβ-amino acid ester from aldehyde and sulfonylimidate was achieved via in situ formation of sulfonylimine and DBU-assisted hydrolysis of sulfonylimidate.

Metal-catalyzed rearrangement of homoallylic ethers to silylmethyl allylic silanes in the presence of a di-tert-butylsilylene source

(Chemical Equation Presented) In examining the scope of the di-rert-butylsilylene transfer to gem-disubstituted alkenes to form silacyclopropanes, we discovered an unprecedented reaction of homoallylic ethers. When silylene transfer was performed at room

Cyclobutanone-3,3-d2 and trimethylene-2,2-d2

An efficient five-step synthesis of cyclobutanone-3,3-d2 is reported. This ketone gives direct access through laser flash photolysis to the trimethylene-2,2-d2 diradical. The life-time of trimethylene-2,2-d2 provides an experimental showing that trimethylene and deuterium-labeled trimethylene diradicals decay to form cyclopropanes, rather than propenes.

The α-secondary isotope effect in the 1,2C rearrangement of cyclopropylchlorocarbene

The experimental α-secondary kinetic isotope effect for the rearrangement of (2,2-dideuteriocylopropyl)chlorocarbene, 2-d2, to chlorocyclobutenes, 4 and 5, is kH/kD = 1.20 at 21° C. The corresponding value calculated by ab initio electronic structure methods is 1.12. The isotope effect very largely originates in hybridization changes at the migrating carbon atom.

Application of 2H N.M.R. Specroscopy to Study the Incorporation of Cadaverine into Quinolizidine Alkaloids

The labelling patterns in (-)-lupinine (3), (-)-sparteine (4), (+)-lupanine (5), (+)-13α-hydroxylupanine (6) and (+)-angustifoline (7), derived biosynthetically from cadaverine dihydrochloride (11) in Lupinus species, have been established by 2H n.m.r. spectroscopy.The presence of 2H at both α and β positions at C-8 in the quinolizidine alkaloids (4) - (7) demonstrates that removal and replacement of hydrogen at this position is not involved in the enzymic processes leading to the tetracyclic skeleton as previously proposed.