1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate - 35193-64-7

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

Catalog Number: EVT-1168570
CAS Number: 35193-64-7
Molecular Formula: C20H13O4P
Molecular Weight: 348.3 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 and organic synthesis. These chiral phosphoric acids and their related complexes have been extensively studied due to their ability to catalyze a variety of enantioselective reactions, including carbon-carbon bond-forming processes and asymmetric hydrogenations145. The unique structural features of these compounds, such as their atropisomerism and the presence of multiple functional groups, allow for a wide range of applications in synthetic chemistry and material science.

Applications in Various Fields

Organic Synthesis

In organic synthesis, binaphthyl-derived phosphoric acids have been utilized as versatile catalysts for enantioselective transformations. They have been particularly effective in reactions such as the 1,3-dipolar cycloaddition of azomethine ylides to electron-deficient olefins, providing access to pyrrolidines with excellent optical purity3. Additionally, these catalysts have been employed in the asymmetric hydrogenation of prochiral carboxylic acids, such as itaconic acid, under mild conditions, achieving high enantioselectivities5.

Material Science

In material science, binaphthyl-diyl hydrogen phosphate has been used as an organocatalyst for the ring-opening polymerization of lactones, leading to the functionalization of polylactones with monosaccharides. This application demonstrates the potential of these compounds in the synthesis of biodegradable polymers with specific end-functionalization, which could have implications for drug delivery and biomaterials6.

Analytical Chemistry

In analytical chemistry, binaphthyl-2,2'-diyl hydrogen phosphate has been employed as a chiral selector for the resolution of helicenes using high-performance liquid chromatography (HPLC). This application highlights the ability of these compounds to separate enantiomers, which is crucial for the pharmaceutical industry and the study of chiral drugs7.

Environmental and Green Chemistry

The development of water-soluble derivatives of binaphthyl compounds, such as the sulfonated 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (binap), has enabled asymmetric hydrogenation reactions to be performed in water. This innovation represents a step towards more environmentally friendly and sustainable chemical processes8.

Properties

CAS Number

35193-64-7

Product Name

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

IUPAC Name

13-hydroxy-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

C20H13O4P

Molecular Weight

348.3 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)

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 as catalysts typically involves the activation of substrates through hydrogen bonding and the stabilization of transition states. For instance, in carbon-carbon bond-forming reactions, these catalysts have been shown to function as efficient enantioselective Brønsted-acid catalysts1. In the case of 1,3-dipolar cycloaddition reactions, theoretical calculations suggest that the catalysts activate both the dipole and dipolarophile simultaneously through the formation of hydrogen bonds, leading to high levels of stereoselectivity3. Similarly, in asymmetric hydrogenation reactions, the binaphthyl-derived ligands in metal complexes can induce high enantioselectivity by controlling the orientation of the substrates and intermediates at the metal center45.

Method of Synthesis or Extraction
1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate can be synthesized using various methods, including the reaction of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate with phosphorus oxychloride or phosphorus pentoxide, or the reaction of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate with phosphoric acid. The efficiency and yield of each method depend on the reaction conditions, such as temperature, solvent, and catalyst. However, the synthesis of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate requires careful consideration of environmental and safety considerations, as some of the reagents used in the synthesis process can be hazardous.
Chemical Structure and Biological Activity
1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate is a chiral molecule that consists of two naphthyl rings connected by a phosphate group. The chiral nature of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate makes it an attractive molecule for asymmetric synthesis and catalysis. 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate exhibits a wide range of biological activities, including anti-inflammatory, antiviral, and anticancer properties. The mechanism of action of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate involves the inhibition of various enzymes and signaling pathways, making it a promising candidate for drug development.
Biological Effects
1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate has been shown to have significant effects on cell function and signal transduction. It has been demonstrated to inhibit the activity of various enzymes, including protein kinases and phosphatases, which play critical roles in cell signaling and regulation. 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate has also been shown to modulate the activity of various transcription factors, which are involved in gene expression and cell differentiation. However, the potential therapeutic and toxic effects of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate require further investigation.
Future Perspectives and Challenges
Despite the promising applications of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate, there are still limitations in its use and study. One of the main challenges is the synthesis of enantiomerically pure 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate, which is essential for its use in asymmetric synthesis and catalysis. Another challenge is the limited understanding of the mechanism of action of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate, which hinders its development as a therapeutic agent. However, with advances in synthetic chemistry and molecular biology, there is great potential for the future application of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate phosphate in scientific research.

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