31352-60-0

Usage

Uses

Used in Pharmaceutical Synthesis:
(S_P)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl phenylphosphinate is used as a ligand in asymmetric synthesis reactions for the production of pharmaceuticals. Its chiral nature helps facilitate the formation of chiral products, which are essential in the development of many drugs.
Used in Agrochemical Synthesis:
In the agrochemical industry, (S_P)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl phenylphosphinate is also utilized as a ligand in asymmetric synthesis reactions. This application aids in the creation of chiral agrochemicals, which can be more effective and selective in their intended use.
Used in Fine Chemicals Synthesis:
(S_P)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl phenylphosphinate is employed in the synthesis of fine chemicals, where its chiral properties are leveraged to produce high-quality and enantiomerically pure products.
Used in Optically Active Materials Production:
(S_P)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl phenylphosphinate has been studied for its potential application in the production of optically active materials. Its ability to impart chirality makes it a promising candidate for creating materials with specific optical properties, which can be useful in various industries, such as electronics and optics.

Upstream product

• 2216-51-5 (-)-menthol 
• 644-97-3 Dichlorophenylphosphine 
• 109-72-8 n-butyllithium 
• 31352-60-0 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl phenylphosphinate 
• 1508260-88-5 (S_p)-menthyl (hydroxymethyl)phenylphosphinate 
• 1779-48-2 phenylphosphinic acid 
• 1508260-88-5 (R_p)-menthyl (hydroxymethyl)phenylphosphinate 
• 100-59-4 phenylmagnesium chloride 
• 95456-31-8 (1R,2S,5R)-(-)-menthyl phosphorodichloridite 
• 591-50-4 iodobenzene 
• 884323-15-3 (1R,2S,5R)-menthyl phosphinate 
• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 14602-86-9 (1R,2S,5R)-menthyl chloroformate 

Downstream Products

• 76095-09-5 menthylphenylphosphonic acid 
• 659749-66-3 [Hydroxy-(3-nitro-phenyl)-methyl]-phenyl-phosphinic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 659749-67-4 [(2,4-Dichloro-phenyl)-hydroxy-methyl]-phenyl-phosphinic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 659749-69-6 (Hydroxy-naphthalen-2-yl-methyl)-phenyl-phosphinic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 76003-53-7 dimenthylphenylpyrophosphonate 
• 76095-10-8 Phenyl-phosphonic acid mono-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester; compound with dicyclohexyl-amine 
• 35671-02-4 S_P-(-)-menthyl O-methyl phenylphosphate 
• 35671-03-5 mentyl methyl (R)_p-phenylphosphonate 
• 1228361-55-4 C₁₆H₂₆NO₂P 

Relevant academic research and scientific papers

Copper-Catalyzed P-H Insertions of α-Imino Carbenes for the Preparation of 3-Phosphinoylindoles

A highly efficient P-H insertion of α-imino copper carbene into H-phosphine oxides, leading to 3-phosphinoylindoles with a broad substrate diversity and good chemoselectivity, is established. This methodology provides a rapid and efficient approach for the C (sp2)-P bond formation via the P-H insertion strategy. The stereoselective P-H insertion of α-imino copper carbene represents a unique example of asymmetric P-H insertion, affording P-stereogenic 3-phosphinoylindoles with high stereoselectivities.

Diastereoselective hydrolysis of asymmetric P-Cl species and synthesis of optically pure (RP)-(-)-menthyl H-phenylphosphinate

Phenyl dichlorophosphine reacted with (L)-(-)-menthol to afford two diastereomers of menthyl phenylphosphinate (RP)-1a/(SP)-1a′ in up to 89:11 dr. Compound (RP)-1a was isolated in 58 % yield (60 g) and > 99:1 dr. An HCl-promoted diastereoselective hydrolysis of the P-Cl species was found to be involved in the reaction. On the basis of this, a mixture of 1a/1a′ with 50:50 dr was converted to a mixture enriched in 1a with 88:12 dr by treatment with phosphorus trichloride.

Palladium-catalyzed one-pot phosphorylation of phenols mediated by sulfuryl fluoride

We report a general palladium-catalyzed one-pot procedure for the synthesis of phosphonates, phosphinates and phosphine oxides from phenols mediated by sulfuryl fluoride. It features mild conditions, broad substrate scope, high functionality tolerance and water insensitivity. The utility of this procedure has been well demonstrated by gram-scale synthesis, sequential synthesis of click chemistry building blocks, late-stage decoration of drugs and natural products and on-DNA synthesis of phosphine oxide for a DNA-encoded library (DEL).

Nickel-Catalyzed Electrosynthesis of Aryl and Vinyl Phosphinates

A mild and useful nickel-catalyzed electrochemical phosphonylation of aryl and vinyl bromides is described. We show that alkyl H-phenylphosphinates can be coupled electrochemically with functionalized aryl and vinyl bromides using very simple conditions (Fe/Ni anode, bench-stable nickel pre-catalyst, undivided cell, galvanostatic electrolysis) to furnish the corresponding aryl and vinyl phosphinates in satisfactory to good yields. Couplings can also be applied to heteroaromatic bromides with some limitations like increased propensity to hydro-dehalogenation.

Alkylation of phosphinite/phosphonite-boranes via temporary protection of the P-H bond

A new alkylation protocol for the synthesis of tertiary phosphonite-/phosphinite-boranes is developed. P-Alkylation products are obtained exclusively in moderate to very good yields from easily accessible (1-hydroxy-1-methylethyl)/(1-hydroxy-1-cyclohexyl) phosphonite/phosphinite-boranes upon reaction with a variety of electrophiles under mild conditions. The methodology opens up new synthetic routes for organophosphorus chemistry and offers access to valuable alkyl phosphonite/phosphinite-boranes. In contrast to previously reported oxidative removal-substitution sequences for the preparation of optically active phosphinite-boranes, our protocol provides a one-step procedure that occurs without loss of stereochemical information at phosphorus. This new approach provides a rather advantageous protocol when compared to direct alkylation methods (which may undergo P-epimerization) and occurs in a stereoselective manner even at 0 °C.

Diselenide-Mediated Catalytic Functionalization of Hydrophosphoryl Compounds

We report a diaryldiselenide catalyst for cross-dehydrogenative nucleophilic functionalization of hydrophosphoryl compounds. The proposed organocatalytic cycle closely resembles the mechanism of the Atherton-Todd reaction, with the catalyst serving as a recyclable analogue of the halogenating agent employed in the named reaction. Phosphorus and selenium NMR studies reveal the existence of a P-Se bond intermediate, and structural analyses indicate a stereospecific reaction.

Preparation method of phosphine chiral center sodium salt (by machine translation)

The method disclosed by the invention is capable of reacting a chiral compound .with a chiral, center compound at 90% a value of, not more than two times to obtain a. phosphine, chiral center, ee sodium salt by reacting, the chiral compound with a Grignard reagent with a Grignard, reagent with a Grignard reagent (), 30. (by machine translation)

Practical Synthesis of Phosphinic Amides/Phosphoramidates through Catalytic Oxidative Coupling of Amines and P(O)?H Compounds

Herein, we report a highly efficient ZnI2-triggered oxidative cross-coupling reaction of P(O)?H compounds and amines. This operationally simple protocol provides unprecedented generic access to phosphinic amides/phosphoramidate derivatives in good yields and short reaction time. Besides, the reaction proceeds under mild conditions, which avoids the use of hazardous reagents, and is applicable to scale-up syntheses as well as late-stage functionalization of drug molecules. The stereospecific coupling is also achieved from readily available optically enriched P(O)?H compounds.

Ni-Catalyzed Asymmetric Allylation of Secondary Phosphine Oxides

A nickel-catalyzed asymmetric allylation of secondary phosphine oxides (SPO) for the synthesis of tertiary phosphine oxides (TPO) was realized with high enantioselectivity. The dynamic kinetic asymmetric transformation of SPO was accomplished in the prese

P-Stereogenic PN(H)P Iron(II) Catalysts for the Asymmetric Hydrogenation of Ketones: The Importance of Non-Covalent Interactions in Rational Ligand Design by Computation

The P-stereogenic PN(H)P pincer ligands (R(Me)PCH2CH2)2NH (R=Cy, (S,S)-1 a; R=tBu, (S,S)-1 b; R=Ph, (R,R)-1 c) and their iron(II) derivatives [FeBr2(CO)(PN(H)P)] (2 a–2 c) and [FeHBr(CO)(PN(H)P)] (3 a–3 c) were developed by DFT-driven ligand design. In a preliminary study, the P(Cy)Me-based pincer (S,S)-1 a and its Fe(II) complex 3 a were prepared, tested in the asymmetric transfer hydrogenation of acetophenone, and studied by Density Functional Theory (DFT). Based on the good agreement between the experimental and calculated enantioselectivity, rational design of the pincer by DFT was attempted, which suggested high enantioselectivity for the tert-butyl and phenyl analogues 3 b and 3 c. Therefore, a new synthetic protocol was developed for (R,R)-1 c using Buono's (S)-(1-(OH)Et)P(Me)Ph?BH3 as P-stereogenic synthon. Against the DFT prediction, 3 c gave 1-phenylethanol with 44% ee, which was reproduced by increasing the level of theory from DFT to post-Hartree-Fock M?ller-Plesset (MP2). This result can be explained by the overestimation of the enantiodeterming CH/π interaction by DFT, which reiterates the need for accurate energies in the assessment of small energy differences such as in asymmetric catalysis. (Figure presented.).