98674-82-9

Usage

Uses

Used in Organic Synthesis:
(R)-(+)-2-HYDROXY-4-(2-METHOXYPHENYL)-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE is used as a building block for the synthesis of biologically active compounds due to its versatile chemical properties and potential for further functionalization.
Used in Asymmetric Catalysis:
In the field of catalysis, (R)-(+)-2-HYDROXY-4-(2-METHOXYPHENYL)-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE is used as a ligand for asymmetric catalysis, enabling the selective formation of enantiomerically pure products, which is crucial for the development of pharmaceuticals and agrochemicals.
Used in the Study of Chiral Molecule Interactions:
(R)-(+)-2-HYDROXY-4-(2-METHOXYPHENYL)-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE is utilized as a valuable tool for investigating the interactions between chiral molecules and biological systems, providing insights into the role of stereochemistry in molecular recognition and biological activity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(+)-2-HYDROXY-4-(2-METHOXYPHENYL)-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE is used as a key intermediate in the synthesis of chiral drugs, contributing to the development of more effective and selective medications.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, (R)-(+)-2-HYDROXY-4-(2-METHOXYPHENYL)-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE is employed as a precursor for the synthesis of chiral pesticides, ensuring targeted pest control with reduced environmental impact.

InChI:InChI=1/C12H17O5P/c1-12(2)8-16-18(13,14)17-11(12)9-6-4-5-7-10(9)15-3/h4-7,11H,8H2,1-3H3,(H,13,14)/t11-/m0/s1

Upstream product

• 98634-23-2 5,5-dimethyl-2-hydroxy-4-(2-methoxyphenyl)-1,3,2-dioxaphosphorinane 2-oxide 

Downstream Products

• 1048380-66-0 (S)-1-methyl-3-phenylpiperazine (+)-anicyphos salt 

Relevant academic research and scientific papers

Diquats with Robust Chirality: Facile Resolution, Synthesis of Chiral Dyes, and Application as Selectors in Chiral Analysis

Diquats with extremely high racemization barriers with ΔG≠theor of 233 kJ mol?1 at 180 °C are described. Reported configurational robustness is due to a combination of two structural features: the rigid o-xylylene tether connecting the nitrogen atoms and the presence of two substituents in the bay region of the bipyridinium scaffold. The straightforward synthesis of diquats, plus facile resolution and derivatization make them attractive for chiral application studies. This is demonstrated by: 1) synthesis of the first non-racemic diquat dyes with pronounced chiroptical properties, and 2) capability of diquats to interact stereospecifically with chiral molecules. This suggests potential for diquat derivatives to be used as chiral selectors in separation methods.

Enantiomeric separations of chiral sulfonic and phosphoric acids with barium-doped cyclofructan selectors via an ion interaction mechanism

New cyclofructan-6 (CF6)-based chiral stationary phases (CSPs) bind barium cations. As a result, the barium-complexed CSPs exhibit enantioselectivity toward 16 chiral phosphoric and sulfonic acids in the polar organic mode (e.g., methanol or ethanol mobile phase containing a barium salt additive). Retention is predominantly governed by a strong ionic interaction between the analyte and the complexed barium cation as well as hydrogen bonding with the cyclofructan macrocycle. The log k versus log [X], where [X] = the concentration of the barium counteranion, plots for LARIHC-CF6-P were linear with negative slopes demonstrating typical anion exchange behavior. The nature of the barium counteranion also was investigated (acetate, methanesulfonate, trifluoroacetate, and perchlorate), and the apparent elution strength was found to be acetate > methanesulfonate > trifluoroacetate > perchlorate. A theory based upon a double layer model was proposed wherein kosmotropic anions are selectively adsorbed to the cyclofructan macrocycle and attenuate the effect of the barium cation. van't Hoff studies for two analytes were conducted on the LARIHC-CF6-P for three of the barium salts (acetate, trifluoroacetate, and perchlorate), and the thermodynamic parameters governing retention and enantioselectivity are discussed. Interestingly, for the entropically driven separations, enantiomeric selectivity can increase at higher temperatures, even with decreasing retention.