10,16-bis(anthracen-9-yl)-13-hydroxy-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2,4,6,8,10,16,18(23),21-nonaen-13-one

• ChemBase ID: 141625
• Molecular Formular: C48H31O4P
• Molecular Mass: 702.731101
• Monoisotopic Mass: 702.1959961
• SMILES: c1ccc2c(c1)cc1ccccc1c2c1cc2ccccc2c2c1OP(=O)(Oc1c2c2c(cc1c1c3ccccc3cc3c1cccc3)CCC=C2)O
• Canonical SMILES: OP1(=O)Oc2c(cc3c(c2c2c(O1)c(cc1c2C=CCC1)c1c2ccccc2cc2c1cccc2)cccc3)c1c2ccccc2cc2c1cccc2
• InChI: InChI=1S/C48H31O4P/c49-53(50)51-47-41(43-35-19-7-1-13-29(35)25-30-14-2-8-20-36(30)43)27-33-17-5-11-23-39(33)45(47)46-40-24-12-6-18-34(40)28-42(48(46)52-53)44-37-21-9-3-15-31(37)26-32-16-4-10-22-38(32)44/h1-5,7-17,19-28H,6,18H2,(H,49,50)
• InChIKey: SZKDXDJLUYHXLW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10,16-bis(anthracen-9-yl)-13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2,4,6,8,10,16,18(23),21-nonaen-13-one
• IUPAC Traditional name: 10,16-bis(anthracen-9-yl)-13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2,4,6,8,10,16,18(23),21-nonaen-13-one
• Synonyms: (11bR)-2,6-Di-9-anthracenyl-4-hydroxy-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide; (R)-3,3′-Bis(9-anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate; (11bR)-2,6-二-9-蒽基-4-羟基-二萘并[2,1-d:1′,2′-f][1,3,2]二噁磷杂庚英-4-氧化物; (R)-3,3′-双(9-蒽基)-1,1′-联萘-2,2′-二基磷酸氢酯

Database IDs

• CAS Number: 361342-51-0
• PubChem SID: 162235859
• PubChem CID: 71310666

CALCULATED PROPERTIES

• Acid pKa: 0.7905442
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 9.766187
• LogD (pH = 7.4): 9.764208
• Log P: 12.140581
• Molar Refractivity: 213.3721 cm^3
• Polarizability: 92.2223 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 288-292 °C (D)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C48H29O4P

DETAILS

Sigma Aldrich - 695718

Application
Catalyst used in asymmetric direct alkylation of α-diazoester via C-H bond cleavage.1
Catalysts used in enantioselective condensation/amine addition reactions
Packaging
100, 500 mg in glass bottle
Protocols & Applications
Reductive Amination using BINOL-Derived Chiral Phosphoric Acids