13-(5-{12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosan-13-yl}-9,9-dimethyl-9H-xanthen-4-yl)-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosane

• ChemBase ID: 141453
• Molecular Formular: C55H76O5P2
• Molecular Mass: 879.136462
• Monoisotopic Mass: 878.51679879
• SMILES: CC1(c2cccc(c2Oc2c1cccc2P1OC2CCC3CCCCC3C2C2C3CCCCC3CCC2O1)P1OC2CCC3CCCCC3C2C2C3CCCCC3CCC2O1)C
• Canonical SMILES: CC1(C)c2cccc(c2Oc2c1cccc2P1OC2CCC3C(C2C2C(O1)CCC1C2CCCC1)CCCC3)P1OC2CCC3C(C2C2C(O1)CCC1C2CCCC1)CCCC3
• InChI: InChI=1S/C55H76O5P2/c1-55(2)41-21-11-23-47(61-57-43-29-25-33-13-3-7-17-37(33)49(43)50-38-18-8-4-14-34(38)26-30-44(50)58-61)53(41)56-54-42(55)22-12-24-48(54)62-59-45-31-27-35-15-5-9-19-39(35)51(45)52-40-20-10-6-16-36(40)28-32-46(52)60-62/h11-12,21-24,33-40,43-46,49-52H,3-10,13-20,25-32H2,1-2H3
• InChIKey: NRCUUPXWQXAMMW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 13-(5-{12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosan-13-yl}-9,9-dimethyl-9H-xanthen-4-yl)-12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosane
• IUPAC Traditional name: 13-(5-{12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosan-13-yl}-9,9-dimethylxanthen-4-yl)-12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosane
• Synonyms: R, R-Reetz X-Diphosphonite; (11bR,11′bR)-4,4′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis-dinaphtho[2,1-d:1′, 2′-f][1,3,2]dioxaphosphepin; S,S-Reetz X-Diphosphonite; (11bS,11′bS)-4,4′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin; R,R-Reetz X-二亚磷酸酯; (11bR,11′bR)-4,4′-(9,9-二甲基-9H-氧杂蒽-4,5-二基)双-二萘并[2,1-d:1′,2′-f][1,3,2]二噁磷杂庚英; S,S-Reetz X-二亚磷酸酯; (11bS,11′bS)-4,4′-(9,9-二甲基-9H-氧杂蒽-4,5-二基)双-二萘并[2,1-d:1′,2′-f][1,3,2]二噁磷杂庚英

Database IDs

• CAS Number: 349114-63-2; 349114-57-4
• MDL Number: MFCD09842740
• PubChem SID: 162235687
• PubChem CID: 71310635

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 13.9082
• LogD (pH = 7.4): 13.9082
• Log P: 13.9082
• Molar Refractivity: 258.8391 cm^3
• Polarizability: 99.92827 Å^3
• Polar Surface Area: 46.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 195-207 °C (dec.); 198-217 °C
• Optical Rotation: [α]22/D +270°, c = 1 in chloroform; [α]22/D -245°, c = 1 in chloroform

Safety Information

• German water hazard class: 3

Product Information

• Empirical Formula (Hill Notation): C55H36O5P2

DETAILS

Sigma Aldrich - 682977

Application
This diphosphonite ligand has been successfully employed in Noyori-type asymmetric transfer hydrogenation of prochiral ketones.1
Packaging
100, 500 mg in glass bottle

Sigma Aldrich - 682869

Application
This diphosphonite ligand has been successfully employed in Noyori-type asymmetric transfer hydrogenation of prochiral ketones.3

• Catalyst for asymmetric hydrogenation of quinolines catalyzed by iridium complexes of BINOL-derived diphosphonites1
• Ligand in asymmetric Ni-catalyzed hydrocyanation of styrene and other vinylarenes2
Packaging
100, 500 mg in glass bottle