17-hydroxy-3,31-diphenyl-16,18-dioxa-17λ5-phosphaheptacyclo[17.12.0.02,15.05,14.08,13.020,29.021,26]hentriaconta-1(31),2,4,6,8,10,12,14,19,21,23,25,27,29-tetradecaen-17-one

• ChemBase ID: 140152
• Molecular Formular: C40H25O4P
• Molecular Mass: 600.597861
• Monoisotopic Mass: 600.14904591
• SMILES: c1ccc(cc1)c1cc2ccc3ccccc3c2c2c1c1c(cc3ccc4ccccc4c3c1OP(=O)(O2)O)c1ccccc1
• Canonical SMILES: OP1(=O)Oc2c(c3c(O1)c1c(cc3c3ccccc3)ccc3c1cccc3)c(cc1c2c2ccccc2cc1)c1ccccc1
• InChI: InChI=1S/C40H25O4P/c41-45(42)43-39-35-29(21-19-27-15-7-9-17-31(27)35)23-33(25-11-3-1-4-12-25)37(39)38-34(26-13-5-2-6-14-26)24-30-22-20-28-16-8-10-18-32(28)36(30)40(38)44-45/h1-24H,(H,41,42)
• InChIKey: YKIJNEDTUDPMNC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 17-hydroxy-3,31-diphenyl-16,18-dioxa-17λ^5-phosphaheptacyclo[17.12.0.0^2,^1^5.0^5,^1^4.0^8,^1^3.0^2^0,^2^9.0^2^1,^2^6]hentriaconta-1(31),2,4,6,8,10,12,14,19,21,23,25,27,29-tetradecaen-17-one
• IUPAC Traditional name: 17-hydroxy-3,31-diphenyl-16,18-dioxa-17λ^5-phosphaheptacyclo[17.12.0.0^2,^1^5.0^5,^1^4.0^8,^1^3.0^2^0,^2^9.0^2^1,^2^6]hentriaconta-1(31),2,4,6,8,10,12,14,19,21,23,25,27,29-tetradecaen-17-one
• Synonyms: (R)-2,2′-Diphenyl-3,3′-biphenanthryl-4,4′-diyl phosphate; (R)-VAPOL phosphoric acid; 18-Hydroxy-8,9-diphenyl-diphenanthro[4,3-d:3′,4′-f][1,3,2]dioxaphosphepin-18-oxide; (R)-(-)-VAPOL hydrogenphosphate; (S)-2,2′-Diphenyl-3,3′-biphenanthryl-4,4′-diyl phosphate; (S)-VAPOL phosphoric acid; (S)-18-Hydroxy-8,9-diphenyl-diphenanthro[4,3-d:3′,4′-f][1,3,2]dioxaphosphepin-18-oxide; (S)-VAPOL hydrogenphosphate; (R)-VAPOL 磷酸; (R)-2,2′-二苯基-3,3′-联菲-4,4′-二基磷酸酯; 18-羟基-8,9-二苯基-联菲并[4,3-d:3′,4′-f][1,3,2]二噁磷杂庚英-18-氧化物; (R)-(-)-VAPOL 磷酸氢酯; (S)-VAPOL 磷酸; (S)-18-羟基-8,9-二苯基-联菲并[4,3-d:3′,4′-f][1,3,2]二噁磷杂庚英-18-氧化物; (S)-2,2′-二苯基-3,3′-联菲-4,4′-二基磷酸酯; (S)-VAPOL 磷酸氢酯

Database IDs

• CAS Number: 871130-18-6; 871130-17-5
• MDL Number: MFCD09265084
• PubChem SID: 162234396; 24885284
• PubChem CID: 11570706

CALCULATED PROPERTIES

• Acid pKa: 0.7798931
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 7.6036286
• LogD (pH = 7.4): 7.601698
• Log P: 9.978072
• Molar Refractivity: 178.3231 cm^3
• Polarizability: 78.16765 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: >400 °C
• Optical Rotation: [α]22/D +412°, c = 1 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C40H25O4P

DETAILS

Sigma Aldrich - 688320

Packaging
100, 500 mg in glass bottle
Application
Catalyst for:
• Benzoyloxylation of (aryl)oxindoles with benzoyl peroxide1
• Enantioselective synthesis of homoaldols and cyclic acetals via kinetic resoln of homoaldols2
• Desymmetrization of mono- and bicyclic N-acyl meso-aziridines by ring opening3,4
• Highly enantioselective addition of imides to imines to give aminals5
• Friedel-Crafts reaction of pyrroles with benzylidenebenzamides6

Sigma Aldrich - 675512

Application
Useful chiral Bronsted acid catalyst in the addition of sulfonamides to Boc-activated aryl imines.6
Catalyst involved in:
• Desymmetrization of meso-aziridines1
• Asymmetric aza-Darzens aziridine synthesis2
• Enantioselective ring-opening of mono-and bicyclic N-acyl meso aziridines3
• Condensation of aldehydes with amino benzenesulfonamides4
• Pictet-Spengler reactions5
Packaging
100, 500 mg in glass bottle
Protocols & Applications
Reductive Amination using BINOL-Derived Chiral Phosphoric Acids