18108-22-0

Usage

Uses

Used in Chemical Synthesis:
(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID is used as a synthetic building block for the development of new compounds and materials. Its unique structure allows for the creation of novel molecules with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID is used as a key intermediate in the synthesis of pharmaceutical compounds. Its versatile structure enables the development of new drugs with improved efficacy and reduced side effects, addressing unmet medical needs.
Used in Agrochemical Industry:
(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID is used as a starting material for the synthesis of agrochemicals, such as pesticides and herbicides. Its unique properties contribute to the development of more effective and environmentally friendly products for agricultural applications.
Used in Materials Science:
(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID is used as a component in the development of advanced materials with specific properties, such as improved mechanical strength, thermal stability, or chemical resistance. These materials can be utilized in various applications, including aerospace, automotive, and electronics industries.
Used in Research and Development:
(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID is used as a research tool for studying the properties and behavior of phosphonic acids and their derivatives. Its unique structure provides valuable insights into the fundamental chemistry of these compounds, leading to the discovery of new applications and improvements in existing technologies.

InChI:InChI=1/C7H10NO3P/c8-7(12(9,10)11)6-4-2-1-3-5-6/h1-5,7H,8H2,(H2,9,10,11)/p-1/t7-/m1/s1

Upstream product

• 100-47-0 benzonitrile 
• 82684-76-2 1-(N-acetylamino)-1-phenylmethyl-phosphonic acid 
• 134981-68-3 (+/-)-diethyl 1-(tert-butoxycarbonylamino)phenylmethylphosphonate 
• 122-52-1 triethyl phosphite 
• 3376-26-9 N-Benzylidenebenzylamine N-oxide 
• 77526-40-0 diethyl ((2,2-dimethylhydrazono)(phenyl)methyl)phosphonate 
• 100-52-7 benzaldehyde 
• 50-00-0 formaldehyd 
• 61-90-5 L-leucine 
• 106019-40-3 α-(N-benzyloxycarbonylamino)benzyl-H-phosphonous acid 
• 104513-37-3 1-(N-Phenylacetylamino)-1-phenylmethylphosphonic acid 
• 18108-19-5 Fluorsulfonylaminophenylmethanphosphonsaeurediethylester 
• 52111-18-9 (Carbamoyl-phenyl-methyl)-phosphonic acid diethyl ester 
• 25881-35-0 (R,S)-<α-(Benzylamino)benzyl>phosphonsaeure 

Downstream Products

• 53558-70-6 α-(N-benzyloxycarbonyl)amino-benzylphosphonic acid 
• 18108-22-0 D-1-Amino-1-phenylmethylphosphonic acid 
• 18108-22-0 L-1-Amino-1-phenylmethylphosphonic acid 
• 104513-37-3 D-1-(N-Phenylacetylamino)-1-phenylmethylphosphonic acid 
• 100-52-7 benzaldehyde 
• 100-47-0 benzonitrile 
• 100-51-6 benzyl alcohol 
• 36992-14-0 L-Phenylalanine phosphonate 
• 37714-06-0 (S)-amino(phenyl)methylphosphonic acid 
• 37714-05-9 (R)-1-amino-1-phenylmethylphosphonic acid 
• 1310128-23-4 C₁₃H₂₃NO₆P₂ 
• 1118747-75-3 methacrylamido(phenyl)methylphosphonic acid 

Relevant academic research and scientific papers

Extremely short H?H distances and intermolecular hydrogen-bonding patterns of dialkyl α-aryl-α-(diphenylmethylamino)methanephosphonates

Single crystal X-ray diffraction studies of four N-benzhydryl protected diethyl α-amino-α-arylmethanephosphonates (aryl = phenyl, 1-naphthyl, 1-anthryl, and 1-pyrenyl) reveal several distinct types of hydrogen bonding, leading to the formation of (a) dime

1-(Acylamino)alkylphosphonic acids—alkaline deacylation

The alkaline deacylation of a representative series of 1-(acylamino)alkylphosphonic acids [(AC)-AAP: (AC) = Ac, TFA, Bz; AAP = GlyP, AlaP, ValP, PglP and PheP] in an aqueous solution of KOH (2M) was investigated. The results suggested a two-stage reaction mechanism with a quick interaction of the hydroxyl ion on the carbonyl function of the amide R-C(O)-N(H)- group in the first stage, which leads to instant formation of the intermediary acyl-hydroxyl adducts of R-C(O?)2-N(H)-, visible in the 31P NMR spectra. In the second stage, these intermediates decompose slowly by splitting of the RC(O?)2-N(H)- function with the subsequent formation of 1-aminoalkylphosphonate and carboxylate ions.

1-(N-Acylamino)alkylphosphonic acids—Deacylation in aqueous solutions

The 1-(N-acylamino)alkylphosphonic acids (AC)-AAP belong to the interesting and potentially of pharmacological importance group of 1-aminoalkylphosphonic acids derivatives. Since susceptibility of (AC)-AAP on hydrolytic deacylation can form important factor influencing their biological activity, we have undertaken deacylation investigations of these compounds in aqueous media. In this article, we present our results on deacylation of various types of 1-(N-acylamino)alkylphosphonic acids (AC)-AAP, including 1-(N-acetylamino)alkyl-phosphonic Ac-AAP, 1-(N-chloroacetylamino)alkylphosphonic acids Mca-AAP, 1-(N-trifluoroacetylamino)alkylphosphonic acids TFA-AAP, and 1-(N-benzoylamino)-alkylphosphonic Bz-AAP, derived from representative 1-aminoalkylphosphonic acids AAP (GlyP, AlaP, ValP, PglP, and PheP) in neutral and 2?M HCl solutions.

A Methylidene Group in the Phosphonic Acid Analogue of Phenylalanine Reverses the Enantiopreference of Binding to Phenylalanine Ammonia-Lyases

Aromatic amino acid ammonia-lyases and aromatic amino acid 2,3-aminomutases contain the post-translationally formed prosthetic 3,5-dihydro-4-methylidene-5H-imidazol-5-one (MIO) group. MIO enzymes catalyze the stereoselective synthesis of α- or β-amino acid enantiomers, making these chemical processes environmentally friendly and affordable. Characterization of novel inhibitors enables structural understanding of enzyme mechanism and recognizes promising herbicide candidates as well. The present study found that both enantiomers of the aminophosphonic acid analogue of the natural substrate phenylalanine and a novel derivative bearing a methylidene at the β-position inhibited phenylalanine ammonia-lyases (PAL), representing MIO enzymes. X-ray methods unambiguously determined the absolute configuration of all tested enantiomers during their synthesis. Enzyme kinetic measurements revealed the enantiomer of the methylidene-substituted substrate analogue as being a mirror image relation to the natural l-phenylalanine as the strongest inhibitor. Isothermal titration calorimetry (ITC) confirmed the binding constants and provided a detailed analysis of the thermodynamic driving forces of ligand binding. Molecular docking suggested that binding of the (R)- and (S)-enantiomers is possible by a mirror image packing. (Figure presented.).

A three-component Mannich-type condensation leading to phosphinic dipeptides-extended transition state analogue inhibitors of aminopeptidases

N-Protected α-aminoalkylphosphinic acids bearing a P-H function were found to be novel practical building blocks in three-component condensations with formaldehyde and secondary amines (amino acids). Such Mannich-type N-phosphonomethylation is a common approach for phosphorus acid derived substrates and leads to multifunctional (phosphonic/amino/carboxylic) compounds of diverse relevance. The utility of this reaction was examined for construction, in a single synthetic step, of advanced phosphinic pseudodipeptides designed to act as extended transition state analogue inhibitors of selected aminopeptidases. Phosphinomethylation of primary amino acids was less efficient and yielded mixtures of products which were separated into individual components, and their structures identified.

Tritylamine (triphenylmethylamine) in organic synthesis; III. The synthesis of 1-aminoalkylphosphonic acids in the reaction of N-(triphenylmethyl) alkanimines with phosphorus trichloride in acetic acid or with phosphonic (phosphorous) acid in acetic anhydride

The reaction of phosphorus trichloride in acetic acid or phosphonic (phosphorous) acid in acetic anhydride, with N-(triphenylmethyl)alkanimines gives 1-acetylaminoalkylphosphonic acids 1a-j, which after hydrolysis give 1-aminoalkylphosphonic acids 2a-j in good yields. ARKAT USA, Inc.

POLYMERIZABLE PHOSPHONIC ACID DERIVATIVE AND ADHESIVE COMPOSITION COMPRISING THE SAME

The present invention provides an adhesive composition comprising a polymerizable phosphonic acid derivative which is a composition having intramolecularly a polymerizable group and a phosphonic acid group, represented by the general formula [1]: wherein R represents a polymerizable group;A represents an oxygen atom or a sulfur atom;Xqs represent independently an oxygen atom or a sulfur atom;Yqs represent independently the same or different organic group;Zqs may be independently the same or different from each other and, a part of the Zqs optionally selected or all of the Zqs represent organic groups having a substituent which is an organic group other than a polymerizable group and a phosphonic acid group;p is an integer from 1 to 10;q is an integer from 1 to p; when p is 1, q is 1;X1 represents an oxygen atom or a sulfur atom;Y1 represents an organic group;Z1 represents an organic group having one or more of substituents which are organic groups other than an acidic group and a polymerizable group, or a salt thereof. The adhesive composition or the salt thereof according to the present invention improve a shelf life and adhesion properties of an adhesive composition comprising essentially a (meth)acrylate monomer having intramolecularly an acidic group and water in dental treatment.

Tailoring the structure of aminobisphosphonates to target plant P5C reductase

Using the structure of (3,5-dichlorophenyl)aminomethylenebisphosphonic acid as a lead compound, 25 new phosphonates were synthesized and evaluated as possible inhibitors of Arabidopsis thaliana δ1-pyrroline-5- carboxylate (P5C) reductase. Deriv

Unexpected non-stability of aminophosphonates: Limitation of their synthesis using diphenylmethylamine procedure

New diethyl 1-diphenylmethylaminoalkylphosphonates from aldehydes, ketones, diphenylmethylamine and diethyl phosphite were obtained. Their stability in acidic media as determined by 31P NMR spectroscopy strongly depends on the basicity of the nitrogen atom. The bulky N-substituent can drastically decrease the stability of the ester during acidic hydrolysis leading to decomposition products in the retro Kabachnik-Fields like reaction.

Cyclic chlorophosphites as scaffolds for the one-pot synthesis of α-aminophosphonates under solvent-free conditions

New α-aminophosphonates of the type (OCH2CMe 2CH2O)P(O)CH(NHCO2R)(R′) [6a-i, 7a-e, and 8a-c] have been synthesized in high yields by a three-component reaction using (OCH2CMe2CH2O)PCl (3), benzamide (or urethane or benzyl carbamate), and an aldehyde without using any catalyst under solvent-free conditions. This route can be readily adapted for bis-aminophosphonates as well as optically active binaphthoxy α-aminophosphonates; it also tolerates the phenolic -OH group as shown by the synthesis of hydroxy functionalized aminophosphonates. Partial hydrolysis of compounds 7a-d leads to products in which the phosphorinane ring is cleaved first. Compounds (OCH2CMe2CH2O)P(O)CH[NHC(O)Ph] (9-anthryl) (6f) and optically pure (R,S)-(-)-(C20H 12O2)P(O)CH(NHCO2Et)(Ph) (14a) were characterized by X-ray crystallography.