13-hydroxy-10,16-bis(triphenylsilyl)-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: 140524
• Molecular Formular: C56H41O4PSi2
• Molecular Mass: 865.067101
• Monoisotopic Mass: 864.22809949
• SMILES: c1ccc(cc1)[Si](c1ccccc1)(c1ccccc1)c1cc2ccccc2c2c1OP(=O)(Oc1c2c2ccccc2cc1[Si](c1ccccc1)(c1ccccc1)c1ccccc1)O
• Canonical SMILES: OP1(=O)Oc2c(c3c(O1)c(cc1c3cccc1)[Si](c1ccccc1)(c1ccccc1)c1ccccc1)c1ccccc1cc2[Si](c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C56H41O4PSi2/c57-61(58)59-55-51(62(43-25-7-1-8-26-43,44-27-9-2-10-28-44)45-29-11-3-12-30-45)39-41-23-19-21-37-49(41)53(55)54-50-38-22-20-24-42(50)40-52(56(54)60-61)63(46-31-13-4-14-32-46,47-33-15-5-16-34-47)48-35-17-6-18-36-48/h1-40H,(H,57,58)
• InChIKey: BDQOCXQVIFQJRK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 13-hydroxy-10,16-bis(triphenylsilyl)-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(triphenylsilyl)-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: (11bS)-4-Hydroxy-2,6-bis(triphenylsilyl)dinaphtho-[2,1-d1′,2′f]-[1,3,2]-dioxaphosphepin 4-oxide; MacMillan TiPSY catalyst; (S)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate; Carreira SALDIPAC Ligand; (11bR)-4-Hydroxy-2,6-bis(triphenylsilyl)dinaphtho-[2,1-d:1′,2′f]-1,3,2-dioxaphosphepin 4-oxide; (R)-(-)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate; (11bS)-4-羟基-2,6-双(三苯甲硅烷基)二萘并-[2,1-d1′,2′f]-[1,3,2]-二恶磷环庚烷-4-氧化物; MacMillan TiPSY 催化剂; (S)-3,3′-双(三苯甲硅烷基)-1,1′-联萘-2,2′-二酚磷酸酯; (11bR)-4-羟基-2,6-双(三苯甲硅烷基)二萘并-[2,1-d:1′,2′f]-1,3,2-二恶磷环庚烷-4-氧化物; (R)-(-)-3,3′-双(三苯甲硅烷基)-1,1′-联萘-2,2′-二酚磷酸酯

Database IDs

• CAS Number: 791616-55-2; 929097-92-7
• MDL Number: MFCD09265079
• PubChem SID: 162234768; 24885544; 24885235
• PubChem CID: 11643610

CALCULATED PROPERTIES

• Acid pKa: 0.82165414
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 11.3844595
• LogD (pH = 7.4): 11.382821
• Log P: 13.6466
• Molar Refractivity: 246.8287 cm^3
• Polarizability: 104.34282 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 188-193 °C; 329-335 °C
• Optical Rotation: [α]22/D +210°, c = 1 in chloroform; [α]22/D -197°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-36/37
• 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

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C56H41O4PSi2

DETAILS

Sigma Aldrich - 674745

Application
Organocatalyst for the first enatioselective organocatalytic reductive amination reaction.1
Packaging
100 mg in glass bottle
Protocols & Applications
Reductive Amination using BINOL-Derived Chiral Phosphoric Acids

Sigma Aldrich - 680184

Packaging
100 mg in glass bottle
Protocols & Applications
Reductive Amination using BINOL-Derived Chiral Phosphoric Acids