13-{2-[(2-{12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosan-13-yl}cyclohexyl)oxy]cyclohexyl}-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosane

• ChemBase ID: 141454
• Molecular Formular: C52H84O5P2
• Molecular Mass: 851.167882
• Monoisotopic Mass: 850.57939905
• SMILES: C1CCC2C(C1)CCC1C2C2C3CCCCC3CCC2OP(O1)C1CCCCC1OC1CCCCC1P1OC2CCC3CCCCC3C2C2C3CCCCC3CCC2O1
• Canonical SMILES: C1CCC(C(C1)OC1CCCCC1P1OC2CCC3C(C2C2C(O1)CCC1C2CCCC1)CCCC3)P1OC2CCC3C(C2C2C(O1)CCC1C2CCCC1)CCCC3
• InChI: InChI=1S/C52H84O5P2/c1-5-17-37-33(13-1)25-29-43-49(37)50-38-18-6-2-14-34(38)26-30-44(50)55-58(54-43)47-23-11-9-21-41(47)53-42-22-10-12-24-48(42)59-56-45-31-27-35-15-3-7-19-39(35)51(45)52-40-20-8-4-16-36(40)28-32-46(52)57-59/h33-52H,1-32H2
• InChIKey: WCUSTGBOFYHQJM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 13-{2-[(2-{12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosan-13-yl}cyclohexyl)oxy]cyclohexyl}-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-{2-[(2-{12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosan-13-yl}cyclohexyl)oxy]cyclohexyl}-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 D-Diphosphonite; (11bR, 11′bR)-4,4′-(Oxydi-2,1-phenylene)bis-dinaphtho[2,1-d:, 1′, 2′-f][1,3,2]dioxaphosphepin; S, S-Reetz D-Diphosphonite; (11bS, 11′bS)-4,4′-(Oxydi-2,1-phenylene)bis-dinaphtho[2,1-d: 1′, 2′-f][1,3,2]dioxaphosphepin; R, R-Reetz D-双亚磷酸酯; (11bR, 11′bR)-4,4′-(氧代二-2,1-亚苯基)双-二萘并[2,1-d:, 1′, 2′-f][1,3,2]二噁磷环庚烷; S, S-Reetz D-双亚磷酸酯; (11bS, 11′bS)-4,4′-(氧代二-2,1-亚苯基)双-二萘并[2,1-d: 1′, 2′-f][1,3,2]二噁磷环庚烷

Database IDs

• CAS Number: 898830-89-2; 391860-55-2
• MDL Number: MFCD09842741
• PubChem SID: 162235688
• PubChem CID: 71310636

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 12.601571
• LogD (pH = 7.4): 12.6016
• Log P: 12.6016
• Molar Refractivity: 236.8975 cm^3
• Polarizability: 96.653915 Å^3
• Polar Surface Area: 46.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 171-187 °C; 174-186 °C
• Optical Rotation: [α]22/D +123°, c = 1 in chloroform; [α]22/D -85.0°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Flammable (F); Harmful (Xn)
• UN Number: 3175
• German water hazard class: 3
• Hazard Class: 4.1
• Packing Group: 2
• Risk Statements: 63-11-48/20-67; 63-48/20
• Safety Statements: 36/37
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H228-H315-H336-H361d-H373; H228-H315-H361d-H373
• GHS Precautionary statements: P210-P261-P281; P210-P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3175 4.1/PG 2

Product Information

• Empirical Formula (Hill Notation): C52H32O5P

DETAILS

Sigma Aldrich - 682985

Application
This diphosphonite ligand has been successfully employed in asymmetric Rh-catalyzed conjugate addition reactions of arylboronic acids to enones, as well as in asymmetric hydrogenation reactions of β-keto esters.1,2
Packaging
100, 500 mg in glass bottle

Sigma Aldrich - 682993

Application
This diphosphonite ligand has been successfully employed in asymmetric Rh-catalyzed conjugate addition reactions of arylboronic acids to enones, as well as in asymmetric hydrogenation reactions of β-keto esters.1,2
Packaging
100, 500 mg in glass bottle