90965-06-3

Basic information

• Product Name: (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER
• Synonyms: DIMETHYL (1-DIAZO-2-OXOPROPYL)PHOSPHONATE;(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER;(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER BESTMANN OHIRA REAGENT;1-Diazoacetonylphosphonic Acid Dimethyl Ester;Dimethyl 1-Diazoacetonylphosphonate;Ohira-Bestmann reagent;diMethyl(1-diazo-2-oxopropyl)phosphanate;Phosphonic acid,P-(1-diazo-2-oxopropyl)-, diMethyl ester
• CAS NO: 90965-06-3
• Molecular Formula: C₅H₉N₂O₄P
• Molecular Weight: 192.11
• Mol File: 90965-06-3.mol

Chemical Properties

• Flash Point: 2℃
• Appearance: /
• Density: 1.28
• Refractive Index: n20/D1.352-1.354
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol (Slightly)
• Merck: 14,1177
• BRN: 4247670
• CAS DataBase Reference: (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER(90965-06-3)
• EPA Substance Registry System: (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER(90965-06-3)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-26-36/37
• RIDADR: UN 1648 3 / PGII
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 90965-06-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER is used as a reagent for the transformation of aldehydes to terminal alkynes and ketones to methyl enol ethers, enabling the synthesis of a wide range of organic compounds.
Used in Ethynyl Compound Synthesis:
In the field of organic chemistry, (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER is used as a reagent for the synthesis of ethynyl compounds (alkynes) from aldehydes, which are important building blocks in the creation of various organic molecules.
Used in Isoquinoline and Pyridine N-Oxide Synthesis:
(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER is used as a cyclization agent with oximes in the presence of a Rh catalyst to synthesize isoquinoline and pyridine N-oxides, which are valuable compounds in pharmaceutical and chemical research.
Used in Dimethyl(diazomethyl)phosphonate Synthesis:
Through methanolysis, (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER can be converted into Dimethyl(diazomethyl)phosphonate, which is further employed as a reagent in the synthesis of enol ethers or alkynes, expanding its applications in organic synthesis.
Used in Heterocyclic Scaffold Synthesis:
(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER is used in the synthesis of five-membered heterocyclic scaffolds, such as pyrazoles, triazoles, and oxazoles, through cycloaddition reactions and multicomponent reactions, contributing to the development of novel heterocyclic compounds with potential applications in various fields.

InChI:InChI=1/C5H9N2O4P/c1-4(8)5(7-6)12(9,10-2)11-3/h1-3H3

Upstream product

• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 2158-14-7 4-acetamidobenzenesulfonyl azide 
• 941-55-9 4-toluenesulfonyl azide 

Downstream Products

• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 26530-60-9 trimethyl 2-phosphonopropionate 
• 2243-98-3 1-undecyne 
• 19096-89-0 methoxymethylenecyclohexane 
• 162107-48-4 tert-butyl (R)-4-ethynyl-2,2-dimethyloxazolidine-3-carboxylate 
• 189952-75-8 (S)-3-[2-(Benzyl-tert-butoxycarbonyl-amino)-ethyl]-2-ethyl-hex-5-ynoic acid methyl ester 
• 273944-71-1 (3S,4R,5R,6R,7R,8R)-8-benzoyloxy-6-diethylisopropylsilyloxy-4-hydroxy-3-methoxy-5,7-dimethylnon-1-yne 
• 302554-00-3 (2R,3S)-1-O-tritylhex-5-yne-1,2,3-triol 
• 56017-85-7 (S)-4-ethynyl-2,2-dimethyl-1,3-dioxolane 
• 339193-66-7 {1-[4-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-ylmethyl]-prop-2-ynyl}-methyl-carbamic acid tert-butyl ester 
• 344315-35-1 C₄₁H₅₆O₆S₂Si 
• 67099-42-7 3,3-Dimethyl-5-benzyloxy-1-pentin 
• 143327-83-7 O-tert-butyl N-(S)-(5-methylhex-1-yn-3-yl)carbamate 
• 143327-79-1 ((S)-1-benzyl-2-prop-2-ynyl)carbamic acid t-butyl ester 

Relevant articles and documents

Unveiling novel 2-cyclopropyl-3-ethynyl-4-(4-fluorophenyl)quinolines as GPCR ligands via PI3-kinase/PAR-1 antagonism and platelet aggregation valuations; development of a new class of anticancer drugs with thrombolytic effects

In the present study, novel 2-cyclopropyl-3-ethynyl-4-(4-fluorophenyl) quinolines (4a-l) were recognized and evaluated as G-Protein Coupled Receptor (GPCR) ligands through molecular evaluations. Thrombin mediates adhesion of mast cell, a type of cell abundantly found in connective tissue and releasing histamine and other substances during inflammatory and allergic reactions, through phosphoinositol 3-kinase pathway. With this background, as preliminary, 4a-l are resolute to be potential leads, designated from their effective phosphoinositol 3-kinase (PI3-Kinase) inhibition potentials, best-docked scores, comparative ligand efficiency, and significant structural attributes evaluated by ab initio simulations. Since thrombin is one of the main reason for various cancer invasion in association with PI3Kinase, a thrombolytic potential of the compounds also analyzed. The experimental in vitro studies confirmed the significant enhancement as PI3Kinase inhibitors and appreciable enhancement in MTT assay of breast and skin cancer cell lines. Significantly, acetophenone substituent in the quinoline scaffold could be coherent to note the significant binding affinity to all the evaluated drug targets.

The New Chemical Reporter 6-Alkynyl-6-deoxy-GlcNAc Reveals O-GlcNAc Modification of the Apoptotic Caspases That Can Block the Cleavage/Activation of Caspase-8

O-GlcNAc modification (O-GlcNAcylation) is required for survival in mammalian cells. Genetic and biochemical experiments have found that increased modification inhibits apoptosis in tissues and cell culture and that lowering O-GlcNAcylation induces cell death. However, the molecular mechanisms by which O-GlcNAcylation might inhibit apoptosis are still being elucidated. Here, we first synthesize a new metabolic chemical reporter, 6-Alkynyl-6-deoxy-GlcNAc (6AlkGlcNAc), for the identification of O-GlcNAc-modified proteins. Subsequent characterization of 6AlkGlcNAc shows that this probe is selectively incorporated into O-GlcNAcylated proteins over cell-surface glycoproteins. Using this probe, we discover that the apoptotic caspases are O-GlcNAcylated, which we confirmed using other techniques, raising the possibility that the modification affects their biochemistry. We then demonstrate that changes in the global levels of O-GlcNAcylation result in a converse change in the kinetics of caspase-8 activation during apoptosis. Finally, we show that caspase-8 is modified at residues that can block its cleavage/activation. Our results provide the first evidence that the caspases may be directly affected by O-GlcNAcylation as a potential antiapoptotic mechanism.

Self-organizing oligothiophene-nucleoside conjugates: Versatile synthesis via "Click"-chemistry

A versatile synthesis of novel oligothiophene-nucleoside conjugates based on Cu(l)-catalyzed alkyne-azide cycloaddition ("click-reaction") has been developed. Complementary thymidine- and adenosine-functionalized quaterthiophenes form recognition-driven superstructures via hydrogen bonding and other competing intermolecular forces. Self-aggregated fibers up to 30 μm in length were characterized with atomic force microscopy.

Guiding suprastructure chirality of an oligothiophene by a single amino Acid

Within the present work, synthesis and properties of three stereoisomeric hybrid materials consisting of a π-conjugated oligothiophene backbone and a single amino acid (proline), which is attached by click chemistry, are described. The hybrids were in particular investigated regarding their self-assembling behavior in solution. From optical investigations, including circular dichroism spectroscopy, the formation of chiral suprastructures could be deduced and correlated with the stereochemistry of the proline residue. In addition, an elaborate theoretical model of the compounds' self-assembly into suprastructures was developed on the basis of the experimental findings.

Tuning Excited-State Properties of [2.2]Paracyclophane-Based Antennas to Ensure Efficient Sensitization of Lanthanide Ions or Singlet Oxygen Generation

The multistep synthesis of original antennas incorporating substituted [2.2]paracyclophane (pCp) moieties in the π-conjugated skeleton is described. These antennas, functionalized with an electron donor alkoxy fragment (A1) or with a fused coumarin derivative (A2), are incorporated in a triazacyclonane macrocyclic ligand L1 or L2, respectively, for the design of Eu(III), Yb(III), and Gd(III) complexes. A combined photophysical/theoretical study reveals that A1 presents a charge transfer character via through-space paracyclophane conjugation, whereas A2 presents only local excited states centered on the coumarin-paracyclophane moiety, strongly favoring triplet state population via intersystem crossing. The resulting complexes EuL1 and YbL2 are fully emissive in red and near-infrared, respectively, whereas the GdL2 complex acts as a photosensitizer for the generation of singlet oxygen.

Application of FSO2N3 in preparation of diazo reagent

The invention discloses application of FSO2N3 in preparation of a diazo reagent. The application comprises the following step: in the presence of alkali, FSO2N3 and acetone dimethyl phosphate as shown in a formula 2 are subjected to a reaction as shown in the specification, and a Bestmann-Ohira and/or Seyferth-Gilbert reagent is obtained. According to the application, the Seyferth-Gilbert reagent and/or the Bestmann-Ohira reagent can be obtained at a high yield in half an hour, the two mixed reagents generated in the reaction do not need to be separated, and the one-pot method is directly applied to the synthesis of the terminal alkyne compound. And/or like.

Synthesis of the C1-C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments

The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens. Aside from two stereocenters installed through cytochrome P450 oxidations, their stereochemistry has been predicted by sequence analysis of the polyketide synthase. We report a synthesis of the C1-C27 fragment of stambomycin D, the spectroscopic data of which correlates well with that of the natural product, further validating predictive sequence analysis as a powerful tool for stereochemical assignment of complex polyketide natural products.

Ambruticins: tetrahydropyran ring formation and total synthesis

The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formedviathe AmbJ catalysed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclisation to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J is described as well as model studies involving epoxidation and cyclisations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were unitedviaa Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alcohol gave, after hydrolysis of the lactone, ambruticin J.

Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis

Allylamines are versatile building blocks in the synthesis of various naturally occurring products and pharmaceuticals. In contrast to terminal allylamines, the methods of synthesis of their branched congeners with internal, stereodefined double bonds are less explored. This work describes a new approach for the preparation of allylaminesviacross-coupling of alkyl bromides with simple 3-bromoallylamines by merging the photoredox approach and Ni catalysis. The reaction proceeds under mild conditions, under blue light irradiation, and in the presence of an organic dye, 4CzIPN, as a photocatalyst. The scope of suitable reaction partners is broad, including alkyl bromides bearing reactive functionalities (e.g., esters, nitriles, aldehydes, ketones, epoxides) andN-protected allylamines, as well asN-allylated secondary and tertiary amines and heterocycles. The employment of non-racemic starting materials allows for rapid and easy construction of complex multifunctional allylamine derivatives without the loss of enantiomeric purity.

Structure-Elucidating Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone C §

The (polyenoyl)tetramic acid militarinone C (1) heads a family of seven members. Before our work, the configuration of C-5 was unknown whereas the configurations of C-8′ and C-10′ were either (R,R) or (S,S). We synthesized the four stereoisomers of constitution 1, which conform with these insights. This included cross-coupling both enantiomers of the western building block (8) with both enantiomers of the eastern building block (9). The specific rotations of the resulting 1 isomers suggested that natural 1 is configured like the coupling partners (S)-8 and (R,R)-9. This conclusion was corroborated by degrading natural 1 to alcohol 35 and by proving its configurational identity with synthetic (R,R)-35.