2-(diphenylphosphanyl)-N-[(1S,8S,15R,16R)-16-[2-(diphenylphosphanyl)benzamido]tetracyclo[6.6.2.02,7.09,14]hexadeca-2(7),3,5,9(14),10,12-hexaen-15-yl]benzamide

• ChemBase ID: 142562
• Molecular Formular: C54H42N2O2P2
• Molecular Mass: 812.871002
• Monoisotopic Mass: 812.27215185
• SMILES: c1ccc(cc1)P(c1c(cccc1)C(=O)N[C@H]1[C@@H]([C@H]2c3c(cccc3)[C@@H]1c1c2cccc1)NC(=O)c1c(cccc1)P(c1ccccc1)c1ccccc1)c1ccccc1
• Canonical SMILES: O=C(c1ccccc1P(c1ccccc1)c1ccccc1)N[C@@H]1[C@@H]2c3ccccc3[C@H]([C@H]1NC(=O)c1ccccc1P(c1ccccc1)c1ccccc1)c1c2cccc1
• InChI: InChI=1S/C54H42N2O2P2/c57-53(45-33-17-19-35-47(45)59(37-21-5-1-6-22-37)38-23-7-2-8-24-38)55-51-49-41-29-13-15-31-43(41)50(44-32-16-14-30-42(44)49)52(51)56-54(58)46-34-18-20-36-48(46)60(39-25-9-3-10-26-39)40-27-11-4-12-28-40/h1-36,49-52H,(H,55,57)(H,56,58)/t49-,50+,51-,52-/m1/s1
• InChIKey: BEKZNCOFLFMFHP-HRHVFIINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(diphenylphosphanyl)-N-[(1S,8S,15R,16R)-16-[2-(diphenylphosphanyl)benzamido]tetracyclo[6.6.2.0^2,^7.0^9,^1^4]hexadeca-2(7),3,5,9(14),10,12-hexaen-15-yl]benzamide
• IUPAC Traditional name: 2-(diphenylphosphanyl)-N-[(1S,8S,15R,16R)-16-[2-(diphenylphosphanyl)benzamido]tetracyclo[6.6.2.0^2,^7.0^9,^1^4]hexadeca-2(7),3,5,9(14),10,12-hexaen-15-yl]benzamide
• Synonyms: (+)-(11R,12R)Bis[2′-(diphenylphosphino)benzamido]-9,10-dihydro-9,10-ethanoanthracene; (11R,12R)-N,N′-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)]benzamide; (R,R)-ANDEN-Phenyl Trost Ligand; (+)-(11R,12R)双[2′-(二苯基膦)苯甲酰氨基]-9,10-二氢-9,10-乙基桥蒽; (11R,12R)-N,N′-(9,10-二氢-9,10-乙基桥蒽-11,12-二基)双[2-(二苯基膦)]-苯甲酰胺; (R,R)-ANDEN-苯基 Trost 配体

Database IDs

• CAS Number: 152140-65-3
• MDL Number: MFCD12546007
• PubChem SID: 162236789
• PubChem CID: 11193683

CALCULATED PROPERTIES

• Acid pKa: 14.905919
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 11.1751995
• LogD (pH = 7.4): 11.1751995
• Log P: 11.1752
• Molar Refractivity: 244.3198 cm^3
• Polarizability: 94.58868 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 125-130 °C
• Optical Rotation: [α]22/D -100°, 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

• Grade: technical grade
• Empirical Formula (Hill Notation): C54H42N2O2P2

DETAILS

Sigma Aldrich - 697591

Application
Asymmetric allylic alkylation ligand.4,5,6,7
Catalyst involved in asymmetric allylic alkylations1,2,3
Packaging
100, 500 mg in glass bottle
Legal Information
Sold in collaboration with Dr. Reddy′s Laboratories for research purposes only. US Patent 5739396 applies.