18741-85-0

Usage

Uses

Used in Chemical Synthesis:
(R)-(+)-2,2'-Diamino-1,1'-binaphthalene is used as a chiral ligand for enantioselective catalysis in chemical synthesis, enabling the creation of enantiomerically pure compounds with high selectivity.
Used in Pharmaceutical Industry:
(R)-(+)-2,2'-Diamino-1,1'-binaphthalene is used as a key intermediate in the synthesis of pharmaceutical compounds, particularly those requiring high enantiomeric purity for their therapeutic effects.
Used in Asymmetric Hydrogenations:
(R)-(+)-2,2'-Diamino-1,1'-binaphthalene is used as a catalyst in asymmetric hydrogenations, a crucial process in the production of chiral compounds with specific stereochemistry.
Used in Cyclopropanations:
(R)-(+)-2,2'-Diamino-1,1'-binaphthalene is used as a catalyst in cyclopropanations, a chemical reaction that forms cyclopropane rings, which are important structural motifs in various biologically active molecules.
Used in Chiral Lactone Synthesis:
(R)-(+)-2,2'-Diamino-1,1'-binaphthalene is used as a catalyst in the formation of chiral lactones, which are valuable building blocks in the synthesis of natural products and pharmaceuticals.
Used in the Synthesis of Sterically Hindered Binaphthalene-based Monophosphane Ligands:
(R)-(+)-2,2'-Diamino-1,1'-binaphthalene is used as a starting material for the synthesis of sterically hindered binaphthalene-based monophosphane ligands, which are essential in various catalytic applications, particularly in the field of homogeneous catalysis.

Synthesis

(R)-(+)-2,2'-Diamino-1,1'-binaphthalene can be 1a , 2b, potassium carbonate, potassium iodide, dimethyl sulfoxide as a reaction solvent, then react with adding potassium hydroxide, and finally extract with ethyl acetate And get.

Upstream product

• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 
• 7647-01-0 hydrogenchloride 
• 970-62-7 2,2'-hydrazonaphthalene 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 
• 3857-83-8 2-naphthyl triflate 
• 613-64-9 1,2-di(naphthalen-2-yl)hydrazine 
• 135-19-3 β-naphthol 
• 582-02-5 1,2-di(naphthalen-2-yl)diazene oxide 
• 581-89-5 2-nitronaphthalene 
• 67-56-1 methanol 
• 582-08-1 2,2'-azonaphthalene 
• 91-59-8 naphthalen-2-ylamine 
• 13672-18-9 benzyl-2-naphthylamine 

Relevant academic research and scientific papers

A miniaturized analytical method based on molecularly imprinted absorbents for selective extraction of (S)-1,1′-binaphthyl-2,2′-diamine and combinatorial screening of polymer precursors by computational simulation

Chiral resolution of binaphthylamine is often a toilful conundrum in the field of analytical chemistry and biomedicine. The work puts forward a selective, sensitive, and miniaturized analytical method based on molecularly imprinted polymers (MIPs) as adsorbent for miniaturized tip solid-phase extraction (MTSPE) in the separation of binaphthylamine enantiomer. This method combines the advantages of MIPs (high selectivity), MTSPE (low consumption), and high-performance liquid chromatography (HPLC, high sensitivity). A simple synthesis methodology of MIP (P2) was conducted through bulk polymerization with (S)-(?)-1,1′-binaphthyl-2,2′-diamine (S-DABN) as template together with methacrylic acid monomer, and ethylene glycol dimethacrylate as cross-linker in proper porogen, realizing a selective recognition and efficient enrichment for S-DABN. The method exhibited appreciable linearity (0.06–1.00 mg ml?1), low quantification limit (0.056 mg ml?1), good absolute recoveries (45.70%–69.29%), and high precision (relative standard deviations ≤ 3.54%), along with low consumption (0.50?ml sample solution and 25.0?mg adsorbent). Based on the density functional theory, computational simulation was used to make a preliminary prediction for rational design of MIPs and gave a reasonable elaboration involving the potential mechanism of templates interacting with functional monomers. The adsorption kinetics and thermodynamics were investigated to evaluate the recombination process of substrates. In addition, the selectivity of MIPs for S-DABN was obtained by MIP-MTSPE coupled with HPLC, which supports the feasibility of this convenient design process. The proposed method was employed for selective extraction of S-DABN and exhibited promising potential in the application of chiral analysis.

Synthesis and Optical Properties of Axially Chiral Bibenzo[ b]carbazole Derivatives

Pure organic materials with the circularly polarized luminescence (CPL) property have attracted significant research interest over the past few decades. In this study, a series of axially chiral bibenzo[b]carbazole derivatives were synthesized by adopting

Method for resolving chiral compound

The invention relates to the field of organic chemistry, in particular to a method for resolving a chiral compound. The method for splitting the chiral compound provided by the invention comprises thestep of carrying out addition reaction on a racemic compound shown as a formula A and azodicarbonic acid ester in the presence of a catalyst so as to provide an S-configuration compound shown as theformula A and an S-configuration compound shown as the formula C. According to the method, chiral phosphoric acid is used as a catalyst; good catalytic effect is achieved, and very wide substrate applicability is also achieved; the product and the recovered raw material can be obtained with excellent enantioselectivity, the selectivity coefficient of kinetic resolution can reach 371, and the method has an excellent kinetic resolution effect on various N-monosubstituted and N-unsubstituted binaphthalene diamines, H8-binaphthalene diamines and biphenyl diamines.

A Versatile Method for Kinetic Resolution of Protecting-Group-Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation

A versatile kinetic resolution of protecting-group-free BINAMs and NOBINs has been realized through chiral phosphoric acid catalyzed triazane formation with azodicarboxylates. A series of mono-N-protected and unprotected BINAMs, diphenyl diamines and NOBIN derivatives could be kinetically resolved with excellent performances (with s factor up to 420). The gram-scale reactions and facile derivatizations of the chiral products demonstrate the potential of these methods in the asymmetric synthesis of chiral catalysts and ligands.

Switchable Smiles Rearrangement for Enantioselective O-Aryl Amination

Asymmetric assembly of atropisomeric anilines from abundant and readily available precursors is one of the most challenging but valuable processes in organic synthesis. The use of highly efficient Smiles rearrangement to accomplish switchable enantioselec

Method for catalytical asmmytrical synthesis of binaphthyldiamine

The invention belongs to the field of asmmytric synthesis and discloses a method for catalytical asmmytrical synthesis of binaphthyldiamine. The method comprises the following steps of by taking metaltriflates and a chiral bisoxazoline ligand as catalysts

Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations

We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2–CSP 4).

Chiral aromatic amine compounds and preparation method thereof

The invention discloses chiral aromatic amine compounds and a preparation method thereof. The chiral aromatic amine compounds are characterized in that under the alkaline condition, compounds I reactwith compounds II to obtain corresponding products, namely chiral aromatic amine compounds labeled by compounds with structural formulas III, IV and V or enantiomers, despinners, diastereoisomers or isotopes thereof: (the formula is shown in the description), wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16 and R17 are separately selected from any group, and X is chlorine or bromine. The chiral aromatic amine compounds with high optical purity (an ee value is greater than 99 percent) have wide application in the fields of bioactivity, materials, chiral ligands, chiral catalysts and the like, and can be further derived to prepare recemic or chiral aromatic amine ligands serving as catalyst for asymmetric catalytic reaction. The invention lays a foundation for developing novel catalysts for the asymmetric catalytic reaction and has economic practicality and industrial application prospect.

Chiral separation on various modified amino alcohol-derived HPLC chiral stationary phases

3,5-Dinitrobenzoyl chloride was previously used for the preparation of (R)-phenylglycinol- and (S)-leucinol-derived chiral stationary phases. In this study, 3,5-bis(trifluoromethyl)benzoyl chloride, 2-furoyl chloride, 2-theonyl chloride, 10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonyl chloride, diphenylcarbamoyl chloride, and 1-adamantanecarbonyl chloride were used to prepare six new phenylglycinol-derived chiral stationary phases (CSPs) and five new leucinol-derived CSPs. Using these 11 CSPs, chiral separation of nine π-acidic amino acid derivatives and five π-basic compounds was performed, and the separation results were compared. An adamantyl-derived CSP showed good separation.

Binaphthyl-based chiral bifunctional organocatalysts for water mediated asymmetric List-Lerner-Barbas aldol reactions

Novel binaphthyl-based chiral bifunctional organocatalysts were designed, synthesized and successfully applied to the asymmetric List-Lerner-Barbas aldol reaction in the presence of water. These organocatalysts were found to be effective catalysts for the