(14S)-13-tert-butyl-14-[(12S)-13-tert-butyl-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-12-yl]-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaene

• ChemBase ID: 139285
• Molecular Formular: C52H48P2
• Molecular Mass: 734.885042
• Monoisotopic Mass: 734.3231248
• SMILES: CC(C)(C)P1Cc2ccc3ccccc3c2c2c3ccccc3ccc2[C@H]1[C@@H]1c2ccc3ccccc3c2c2c(ccc3c2cccc3)CP1C(C)(C)C
• Canonical SMILES: CC(P1Cc2ccc3c(c2c2c([C@H]1[C@@H]1c4ccc5c(c4c4c(CP1C(C)(C)C)ccc1c4cccc1)cccc5)ccc1c2cccc1)cccc3)(C)C
• InChI: InChI=1S/C52H48P2/c1-51(2,3)53-31-37-25-23-33-15-7-11-19-39(33)45(37)47-41-21-13-9-17-35(41)27-29-43(47)49(53)50-44-30-28-36-18-10-14-22-42(36)48(44)46-38(32-54(50)52(4,5)6)26-24-34-16-8-12-20-40(34)46/h7-30,49-50H,31-32H2,1-6H3/t49-,50-,53?,54?/m0/s1
• InChIKey: YXMFQIWDFKIXGQ-KUSQLHRJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (14S)-13-tert-butyl-14-[(12S)-13-tert-butyl-13-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-12-yl]-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaene
• IUPAC Traditional name: (14S)-13-tert-butyl-14-[(12S)-13-tert-butyl-13-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-12-yl]-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaene
• Synonyms: (3S,3’S,4S,4’S,11bS,11’bS)-(+)-4,4′-Di-t-butyl-4,4′,5,5′-tetrahydro-3,3′-bi-3H-dinaphtho[2,1-c:1′,2′-e]phosphepin; (S)-BINAPINE; (3S,3'S,4S,4'S,11bS,11'bS)-(+)-4,4′-二-叔丁基-4,4′,5,5′-四氢-3,3′-二-3H-二萘并[2,1-c:1′,2′-e]磷杂庚英; 二叔丁基四氢联二萘磷

Database IDs

• CAS Number: 528854-26-4
• MDL Number: MFCD06658119
• PubChem SID: 24883786; 162233533
• PubChem CID: 66557332

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 12.692063
• LogD (pH = 7.4): 12.706608
• Log P: 12.7068
• Molar Refractivity: 241.4494 cm^3
• Polarizability: 98.80927 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: >300 °C (dec.)(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C52H48P2

DETAILS

Sigma Aldrich - 650870

Application
Demonstates excellent enantioselectivity and reactivity for the asymmetric hydrogenation of Z-β-aryl(β-acylamino)acrylates.1
Chiral Quest Phosphine Ligands for Asymmetric Hydrogenation
Packaging
100, 500 mg in glass bottle