870-50-8 Usage
Description
Di-tert-Butyl azodicarboxylate is an organic compound that serves as a versatile reagent in various chemical reactions and synthesis processes. It is characterized by its ability to participate in multiple types of chemical transformations, making it a valuable component in the fields of organic chemistry and pharmaceutical synthesis.
Uses
Used in Organic Chemistry:
Di-tert-Butyl azodicarboxylate is used as a reagent for the preparation of acyl hydrazinedicarboxylates through photoorganocatalytic hydroacylation of dialkyl azodicarboxylates with aldehydes, in the presence of phenylglyoxylic acid as a photocatalyst. This application highlights its role in facilitating complex organic reactions.
Used in Enantioselective Synthesis:
In the field of enantioselective synthesis, Di-tert-Butyl azodicarboxylate is used as a precursor for the synthesis of 3,6-dihyropyridazines. It is employed in conjunction with organocatalysts such as L-proline or (S)-2-pyrrolidinyl tetrazole, which enable the selective formation of desired enantiomers.
Used in Electrophilic Amination:
Di-tert-Butyl azodicarboxylate is utilized in the electrophilic amination of beta-keto esters, which is catalyzed by an axially chiral guanidine. This application underscores its importance in the synthesis of chiral compounds.
Used in Asymmetric Friedel-Crafts Amination:
In the pharmaceutical industry, Di-tert-Butyl azodicarboxylate is used in asymmetric Friedel-Crafts amination reactions, facilitated by a chiral organocatalyst. This reaction is crucial for the synthesis of enantioselective compounds with potential therapeutic applications.
Used in Peptide Synthesis:
Di-tert-Butyl azodicarboxylate is employed as a starting material in the synthesis of pyrroloisoquinoline templates, which are key structural elements in the development of peptidomimetic compounds. These compounds are designed to mimic the action of peptides and have applications in drug discovery.
Used in Barbier-Type Propargylation Reactions:
Furthermore, Di-tert-Butyl azodicarboxylate is utilized in Barbier-type propargylation reactions, which involve the formation of alkynyl compounds. These reactions are significant in the synthesis of various organic compounds and materials.
Overall, Di-tert-Butyl azodicarboxylate is a multifaceted reagent with applications spanning across various industries, including pharmaceuticals, materials science, and organic chemistry. Its versatility and ability to participate in a wide range of chemical reactions make it an indispensable tool in the synthesis of complex organic compounds and the development of new drugs and materials.
Purification Methods
The tert-butyl ester has the advantage over the ethyl ester (below) in being a solid and more acid labile. It crystallises from ligroin and is best purified by covering the dry solid (22g) with pet ether (b 30-60o, 35-40 mL) heating to boiling and adding ligroin (b 60-90o) until the solid dissolves. On cooling, large lemon yellow crystals of the ester separate (~ 20g), m 90.7-92o. Evaporation of the filtrate gives a further crop of crystals [Carpino & Crowley Org Synth 44 18 1964]. This reagent is useful in the Mitsunobu reaction [Mitsunobu Synthesis 1 1981, Gennari et al. J Am Chem Soc 108 6394 1986, Evans et al. J Am Chem Soc 108 6394 1986, Hughes Org React 42 335 1992, Dodge et al. Org Synth 73 110 1996, Hughes Org Prep Proc Int 28 127 1996, Ferguson & Marcelle J Am Chem Soc 128 4576 2006, see also DEAD and DIAD below].
Check Digit Verification of cas no
The CAS Registry Mumber 870-50-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 0 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 870-50:
(5*8)+(4*7)+(3*0)+(2*5)+(1*0)=78
78 % 10 = 8
So 870-50-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H18N2O4/c1-9(2,3)15-7(13)11-12-8(14)16-10(4,5)6/h1-6H3/b12-11+
870-50-8Relevant articles and documents
Bifunctional Molecular Probes for Activity-Based Visualization of Quinone-Dependent Amine Oxidases
Burke, Ashley A.,Barrows, Luke,Solares, Maria J.,Wall, Alexander D.,Jakobsche, Charles E.
, p. 17681 - 17685 (2018)
The design, synthesis, and evaluation of two bifunctional molecular probes that can be used to visualize quinone-dependent amine oxidase enzymes in an activity-dependent manner are described. These probes use alkylhydrazines to irreversibly bind the target enzymes, which can then be visualized with either Western blotting or in-gel fluorescence. The results show that the Western blotting readout, which utilizes commercially available anti-nitrophenyl antibodies to detect a simple dinitrophenyl antigen, provides a stronger readout than the fluorescein-based fluorescence readout. This visualization strategy can be used to measure the potency of enzyme inhibitors by selectively visualizing the active enzyme that remains after treatment with an inhibitor. Looking forward, this probe molecule and visualization strategy will enable activity-based protein-profiling experiments, such as determining inhibitor selectivity values within full proteome mixtures, for this family of amine oxidase enzymes.
Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis
Zhang, Yunfei,Sim, Jae Hun,Macmillan, Samantha N.,Lambert, Tristan H.
, p. 6026 - 6030 (2020/08/05)
The synthesis of 1,2-dihydroquinolines by the hydrazine-catalyzed ring-closing carbonyl-olefin metathesis (RCCOM) of N-prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of substitution patterns are shown. With an acid-labile protecting group on the nitrogen atom, in situ deprotection and autoxidation furnish quinoline. In comparison with related oxygen-containing substrates, the cycloaddition step of the catalytic cycle is shown to be slower, but the cycloreversion is found to be more facile.
Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light
M?rz,Chudoba,Kohout,Cibulka
, p. 1970 - 1975 (2017/03/11)
The usefulness of flavin-based aerial photooxidation in esterification under Mitsunobu reaction conditions was demonstrated, providing aerial dialkyl azodicarboxylate recycling/generation from the corresponding dialkyl hydrazine dicarboxylate. Simultaneously, activation of triphenylphosphine (Ph3P) by photoinduced electron transfer from flavin allows azo-reagent-free esterification. An optimized system with 3-methylriboflavin tetraacetate (10%), oxygen (terminal oxidant), visible light (450 nm), Ph3P, and dialkyl hydrazine dicarboxylate (10%) has been shown to provide efficient and stereoselective coupling of various alcohols and acids to esters with retention of configuration.