13-hydroxy-10,16-bis(phenanthren-9-yl)-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one

• ChemBase ID: 141755
• Molecular Formular: C48H29O4P
• Molecular Mass: 700.715221
• Monoisotopic Mass: 700.18034604
• SMILES: c1ccc2c(c1)cc(c1c2cccc1)c1cc2ccccc2c2c1OP(=O)(Oc1c2c2ccccc2cc1c1cc2ccccc2c2c1cccc2)O
• Canonical SMILES: OP1(=O)Oc2c(c3c(O1)c(cc1c3cccc1)c1cc3ccccc3c3c1cccc3)c1ccccc1cc2c1cc2ccccc2c2c1cccc2
• InChI: InChI=1S/C48H29O4P/c49-53(50)51-47-43(41-25-29-13-1-5-17-33(29)37-21-9-11-23-39(37)41)27-31-15-3-7-19-35(31)45(47)46-36-20-8-4-16-32(36)28-44(48(46)52-53)42-26-30-14-2-6-18-34(30)38-22-10-12-24-40(38)42/h1-28H,(H,49,50)
• InChIKey: BVICVEIKBNVROI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 13-hydroxy-10,16-bis(phenanthren-9-yl)-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one
• IUPAC Traditional name: 13-hydroxy-10,16-bis(phenanthren-9-yl)-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one
• Synonyms: (R)-3,3′-Bis(9-phenanthryl)-1,1′-binaphthalene-2,2′-diyl hydrogen phosphate; (11bR)-2,6-Di-9-phenanthrenyl-4-hydroxy-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide; (11bR)-2,6-二-9-菲基-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

Database IDs

• CAS Number: 864943-22-6
• MDL Number: MFCD12546016
• PubChem SID: 162235989
• PubChem CID: 11693293

CALCULATED PROPERTIES

• Acid pKa: 0.7864347
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 9.582612
• LogD (pH = 7.4): 9.580651
• Log P: 11.957026
• Molar Refractivity: 211.2235 cm^3
• Polarizability: 93.50722 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 390-400 °C
• Optical Rotation: [α]22/D -44.0°, c = 1 in DMSO

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C48H29O4P

DETAILS

Sigma Aldrich - 700665

Packaging
100 mg in glass bottle
Application
Catalyst for:
• Asymmetric hydrogenation cascade1
• Enantioselective Friedel-Crafts reaction2
• Asymmetric hydrogenation of 2-substituted quinolines3
• Chiral Broensted acid catalyzed enantioselective a-aminoxylation of ene carbamates4
• Preparation of β-carbolines via diastereo- and enantioselective N-acyliminium cyclization cascades of tryptamines and keto acids/esters5
• Asymmetric transfer hydrogenation of substituted quinoxalines6