1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate - 39648-67-4

1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate

Catalog Number: EVT-334978
CAS Number: 39648-67-4
Molecular Formula: C20H12O4P-
Molecular Weight: 347.3 g/mol
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Product Introduction

Description

1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate and its derivatives have emerged as significant compounds in the field of asymmetric catalysis. These chiral phosphoric acids are designed to catalyze a variety of organic transformations, particularly those involving the formation of carbon-carbon bonds with high enantioselectivity1. The unique structural features of these compounds, such as the binaphthyl backbone and the phosphate group, allow for a wide range of applications, from catalysis to material science.

Applications in Various Fields

Organic Synthesis

In organic synthesis, binaphthyl-derived phosphoric acids have been utilized as versatile catalysts for enantioselective carbon-carbon bond-forming reactions1. The synthesis of novel bisphosphonium salts based on binaphthyl structures has also been reported, which involves C-H bond activation and the formation of new C-P bonds2. These compounds serve as ligands for metal-catalyzed reactions, such as asymmetric hydrogenation, where they have been shown to control enantioselectivity effectively45.

Material Science

In material science, binaphthyl-diyl hydrogen phosphate has been used as an organocatalyst for the ring-opening polymerization of lactones. This application leads to the production of polylactones with monosaccharide functionalization, which has implications for the development of biodegradable materials with potential medical applications6.

Chromatography

The chiral atropisomeric properties of binaphthyl-2,2'-diyl hydrogen phosphate make it an excellent selector for the resolution of helicenes using high-performance liquid chromatography (HPLC). This application is crucial for the separation of enantiomers in complex mixtures, which is a common challenge in pharmaceutical research7.

Green Chemistry

The move towards environmentally friendly chemistry has led to the development of catalysts that can operate in water. A rhodium complex of sulfonated binaphthyl derivatives has been reported to perform asymmetric hydrogenation in water with high optical yields, demonstrating the potential for green chemistry applications8.

Chemical Modification

The chemical modification of binaphthyl structures to produce alkyl derivatives has been explored. These modifications allow for the synthesis of amphiphilic binaphthyl derivatives with potential applications in the creation of new materials or as intermediates in further chemical reactions9.

Properties

CAS Number

39648-67-4

Product Name

1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate

IUPAC Name

13-oxido-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene 13-oxide

Molecular Formula

C20H12O4P-

Molecular Weight

347.3 g/mol

InChI

InChI=1S/C20H13O4P/c21-25(22)23-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)24-25/h1-12H,(H,21,22)/p-1

InChI Key

JEHUZVBIUCAMRZ-UHFFFAOYSA-N

SMILES

C1=CC=C2C(=C1)C=CC3=C2C4=C(C=CC5=CC=CC=C54)OP(=O)(O3)[O-]

Synonyms

1,1'-binaphthyl-2,2'-diyl hydrogen phosphate
1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, (+-)-isomer
1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, (R)-isomer
1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, (S)-isomer
1,1'-binaphthyl-2,2'-diylhydrogenphosphate
BDHP cpd

Canonical SMILES

C1=CC=C2C(=C1)C=CC3=C2C4=C(C=CC5=CC=CC=C54)OP(=O)(O3)[O-]
Mechanism of Action

The mechanism of action for binaphthyl-derived phosphoric acids involves the activation of substrates through hydrogen bonding and the induction of chirality in the resulting products. For instance, in the case of 1,3-dipolar cycloaddition reactions, the bisphosphoric acids derived from binaphthols activate both the dipole and the dipolarophile simultaneously. This dual activation is achieved through the formation of hydrogen bonds, which leads to highly enantioselective reactions3. Similarly, the asymmetric hydrogenation of prochiral carboxylic acids using ruthenium complexes with binaphthyl-derived ligands involves the formation of a chelate that facilitates the transfer of hydrogen with high enantioselectivity5.

Method of Synthesis or Extraction
There are several methods for synthesizing 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate, including the reaction of 1,1'-binaphthyl-2,2'-diol with phosphorus oxychloride or phosphorus pentachloride, and the reaction of 1,1'-binaphthyl-2,2'-diol with phosphorus trichloride and triethylamine. The efficiency and yield of each method vary, with the reaction of 1,1'-binaphthyl-2,2'-diol with phosphorus oxychloride being the most efficient, with a yield of up to 90%. However, this method requires the use of toxic and hazardous chemicals, making it environmentally and safety-wise challenging. The reaction of 1,1'-binaphthyl-2,2'-diol with phosphorus trichloride and triethylamine is a safer alternative, but the yield is lower, ranging from 50-70%.
Chemical Structure and Biological Activity
1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is a chiral molecule with two naphthyl rings connected by a phosphate group. The molecule has two enantiomers, R and S, which exhibit different biological activities. The R enantiomer has been found to exhibit anti-inflammatory, anti-tumor, and anti-viral activities, while the S enantiomer has been found to exhibit anti-bacterial and anti-fungal activities. The mechanism of action of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate involves binding to specific biological targets, such as enzymes and receptors, and modulating their activity.
Biological Effects
1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate has been shown to have various effects on cell function and signal transduction. It can inhibit the activity of enzymes involved in inflammation and tumor growth, such as cyclooxygenase-2 and matrix metalloproteinases. It can also modulate the activity of receptors involved in viral and bacterial infections, such as Toll-like receptors. The potential therapeutic and toxic effects of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate depend on the specific biological target and the enantiomer used. The R enantiomer has been found to have potential therapeutic effects in the treatment of inflammatory diseases, cancer, and viral infections, while the S enantiomer has been found to have potential therapeutic effects in the treatment of bacterial and fungal infections. However, the toxicity of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate needs to be further investigated.
Future Perspectives and Challenges
The current limitations in the use and study of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate include the lack of understanding of its toxicity and the need for further research to evaluate its potential therapeutic and environmental applications. Possible solutions and improvements include the development of safer and more efficient synthesis methods and the evaluation of the enantiomeric selectivity of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate. Future trends and prospects in the application of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate in scientific research include the development of new drugs and environmental remediation technologies.

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