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(R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate

Catalog Number
ACM39648674
Product Name
(R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate
Structure
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CAS
39648-67-4
  • Product Overview
  • Usage
Synonyms
(R)-(-)-1,1'-BINAPHTHALENE-2,2'-DIYL-PHOSPHATE; 4-Hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide; (R)-5,5 inverted exclamation mark ,6,6 inverted exclamation mark ,7,7 inverted exclamation mark ,8,8 inverted exclamation mark -Octahydro-1,1 inverted exclamation mark -binaphthyl-2,2 inverted exclamation mark -diyl hydrogen phosphate; -Binaphthyl-2,2; dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-ol 4-oxide; NSC244999; FT-0605235; (+)-4-Hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-oxide; O732; SC-04178;
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 Weight
348.294g/mol
Molecular Formula
C20H13O4P;
Canonical SMILES
C1=CC=C2C(=C1)C=CC3=C2C4=C(C=CC5=CC=CC=C54)OP(=O)(O3)O;
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;
Storage
Refrigerator
Complexity
508
Covalently-Bonded Unit Count
1
EC Number
609-734-1
Exact Mass
348.055g/mol
H-Bond Acceptor
4
H-Bond Donor
1
Heavy Atom Count
25
Monoisotopic Mass
348.055g/mol
NSC Number
244999
Topological Polar Surface Area
55.8A^2
Application
(R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate serves as a versatile chiral ligand employed in various asymmetric synthesis applications. It is especially effective in hydrocarboxylation reactions where it complexes with rhodium, and it facilitates the asymmetric dipolar cycloaddition of diazo compounds. As an acidic resolving agent, it proficiently separates certain racemic amines that are challenging to resolve. This compound also acts as a chiral quenching agent and plays a crucial role in catalyzing asymmetric hetero Diels-Alder reactions using chiral lanthanide(III) complexes. Additionally, it enhances the efficiency of the Mannich reaction. Its utility extends to forming palladium derivatives for asymmetric hydrocarboxylations and rhodium derivatives for dipolar cycloadditions.
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