Catalog Number |
ACM1435948314-1 |
CAS |
1435948-31-4 |
Structure |
![{[CurrentData.Name]}](https://resource.alfa-chemistry.com/structure/1435948-31-4.gif) |
Description |
(R)-3,3'-Bis(3,5-diisopropylphenyl)-[1,1'-binapthalene]-2,2'-diol, also known as (R)-BINAP, is an important chiral ligand used in asymmetric synthesis of organic compounds. It is a widely used compound in chemical and pharmaceutical industries due to its ability to catalyze a variety of reactions with high enantioselectivity. This review will discuss the synthesis of (R)-BINAP, its scientific research applications, its mechanism of action, its biochemical and physiological effects, the advantages and limitations for lab experiments, and the potential future directions of research. |
IUPAC Name |
3-[3,5-di(propan-2-yl)phenyl]-1-[3-[3,5-di(propan-2-yl)phenyl]-2-hydroxynaphthalen-1-yl]naphthalen-2-ol |
Molecular Weight |
606.8 g/mol |
Molecular Formula |
C44H46O2 |
Canonical SMILES |
CC(C)C1=CC(=CC(=C1)C2=CC3=CC=CC=C3C(=C2O)C4=C(C(=CC5=CC=CC=C54)C6=CC(=CC(=C6)C(C)C)C(C)C)O)C(C)C |
InChI |
InChI=1S/C44H46O2/c1-25(2)31-17-32(26(3)4)20-35(19-31)39-23-29-13-9-11-15-37(29)41(43(39)45)42-38-16-12-10-14-30(38)24-40(44(42)46)36-21-33(27(5)6)18-34(22-36)28(7)8/h9-28,45-46H,1-8H3 |
InChI Key |
WSDRIJXMYCUGAH-UHFFFAOYSA-N |
Application |
(R)-BINAP is widely used in asymmetric synthesis of various organic compounds, including chiral drugs, natural products, and polymers. It is particularly useful in the synthesis of polycyclic compounds and chiral alcohols, and has been used in the synthesis of a variety of drugs, including the antimalarial drug artemisinin, the anti-cancer drug paclitaxel, and the anti-HIV drug tenofovir. In addition, (R)-BINAP has been used in the synthesis of natural products, such as the antifungal agents amphotericin B and caspofungin, and the antibiotic cefotaxime. |
Properties |
(R)-BINAP is an inert compound and is not known to have any direct biochemical or physiological effects. However, the compounds synthesized using (R)-BINAP may have biological effects, depending on their structure and function. For example, the antimalarial drug artemisinin, which is synthesized using (R)-BINAP, has been shown to have antimalarial activity in vitro and in vivo. |