SEGPHOS

SEGPHOS

Names
IUPAC name 4,4'-Bi-1,3-benzodioxole-5,5'-diylbis(diphenylphosphane)
Other names SEGPHOS 5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole
Identifiers
CAS Number	244261-66-3 (R) Y 210169-54-3 (S) N
3D model (JSmol)	(RS): Interactive image
ChemSpider	9192694 (RS) N
PubChem CID	11017510 (RS)
InChI InChI=1S/C38H28O4P2/c1-5-13-27(14-6-1)43(28-15-7-2-8-16-28)33-23-21-31-37(41-25-39-31)35(33)36-34(24-22-32-38(36)42-26-40-32)44(29-17-9-3-10-18-29)30-19-11-4-12-20-30/h1-24H,25-26H2 N Key: RZZDRSHFIVOQAF-UHFFFAOYSA-N N
SMILES (RS): C1OC2=C(O1)C(=C(C=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)C5=C(C=CC6=C5OCO6)P(C7=CC=CC=C7)C8=CC=CC=C8
Properties
Chemical formula	C38H28O4P2
Molar mass	610.57 g/mol
Appearance	colorless solid
Solubility in water	organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

SEGPHOS is a chiral ligand developed by Takasago that is used in asymmetric synthesis.^[1] It was developed after BINAP and was investigated since it has a narrower dihedral angle between the aromatic faces. This was predicted and then confirmed to increase the enantioselectivity and activity of metal complexes of SEGPHOS.

In addition to the parent ligand bearing phenyl groups on the phosphorus atoms, the bulkier derivatives DM-SEGPHOS and DTBM-SEGPHOS are also commercially available.^[2] In DM-SEGPHOS and DTBM-SEGPHOS, the phenyl groups of SEGPHOS are replaced by 3,5-dimethylphenyl and 3,5-di-t-butyl-4-methoxyphenyl groups, respectively.

References

1. ↑ Shimizu, H., Nagasaki, I., Matsumura, K., Sayo, N., Saito, T. (2007). "Developments in Asymmetric Hydrogenation from an Industrial Perspective". Acc. Chem. Res. 40 (12): 1385–1393. PMID 17685581. doi:10.1021/ar700101x. CS1 maint: Multiple names: authors list (link)
2. ↑ "SEGPHOS". www.strem.com. Retrieved 2016-08-10.