2-[(1S,3S)-2-{2-[(1S,3S)-5,8-dioxo-1,3-bis(2-{[(1S)-1-phenylethyl]carbamoyl}phenyl)-hexahydro-1H-[1,2,4]diazaphospholo[1,2-a]pyridazin-2-yl]phenyl}-5,8-dioxo-3-(2-{[(1S)-1-phenylethyl]carbamoyl}phenyl)-hexahydro-1H-[1,2,4]diazaphospholo[1,2-a]pyridazin-1-yl]-N-[(1S)-1-phenylethyl]benzamide

• ChemBase ID: 140687
• Molecular Formular: C78H72N8O8P2
• Molecular Mass: 1311.402602
• Monoisotopic Mass: 1310.49483456
• SMILES: C[C@@H](c1ccccc1)NC(=O)c1ccccc1[C@H]1N2C(=O)CCC(=O)N2[C@@H](P1c1ccccc1P1[C@H](N2C(=O)CCC(=O)N2[C@@H]1c1ccccc1C(=O)N[C@@H](C)c1ccccc1)c1ccccc1C(=O)N[C@@H](C)c1ccccc1)c1ccccc1C(=O)N[C@@H](C)c1ccccc1
• Canonical SMILES: O=C1CCC(=O)N2N1[C@@H](P([C@H]2c1ccccc1C(=O)N[C@H](c1ccccc1)C)c1ccccc1P1[C@H](N2N([C@@H]1c1ccccc1C(=O)N[C@H](c1ccccc1)C)C(=O)CCC2=O)c1ccccc1C(=O)N[C@H](c1ccccc1)C)c1ccccc1C(=O)N[C@H](c1ccccc1)C
• InChI: InChI=1S/C78H72N8O8P2/c1-49(53-27-9-5-10-28-53)79-71(91)57-35-17-21-39-61(57)75-83-67(87)45-46-68(88)84(83)76(62-40-22-18-36-58(62)72(92)80-50(2)54-29-11-6-12-30-54)95(75)65-43-25-26-44-66(65)96-77(63-41-23-19-37-59(63)73(93)81-51(3)55-31-13-7-14-32-55)85-69(89)47-48-70(90)86(85)78(96)64-42-24-20-38-60(64)74(94)82-52(4)56-33-15-8-16-34-56/h5-44,49-52,75-78H,45-48H2,1-4H3,(H,79,91)(H,80,92)(H,81,93)(H,82,94)/t49-,50-,51-,52-,75-,76-,77-,78-/m0/s1
• InChIKey: NTWCWWNZWYJTEP-HMVZQFFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,3S)-2-{2-[(1S,3S)-5,8-dioxo-1,3-bis(2-{[(1S)-1-phenylethyl]carbamoyl}phenyl)-hexahydro-1H-[1,2,4]diazaphospholo[1,2-a]pyridazin-2-yl]phenyl}-5,8-dioxo-3-(2-{[(1S)-1-phenylethyl]carbamoyl}phenyl)-hexahydro-1H-[1,2,4]diazaphospholo[1,2-a]pyridazin-1-yl]-N-[(1S)-1-phenylethyl]benzamide
• IUPAC Traditional name: 2-[(1S,3S)-2-{2-[(1S,3S)-5,8-dioxo-1,3-bis(2-{[(1S)-1-phenylethyl]carbamoyl}phenyl)-tetrahydro-[1,2,4]diazaphospholo[1,2-a]pyridazin-2-yl]phenyl}-5,8-dioxo-3-(2-{[(1S)-1-phenylethyl]carbamoyl}phenyl)-tetrahydro-[1,2,4]diazaphospholo[1,2-a]pyridazin-1-yl]-N-[(1S)-1-phenylethyl]benzamide
• Synonyms: Bis[(S,S,S)-DiazaPhos-SPE]; 2,2′,2″,2′′′-(1,2-Phenylenebis[(1S,3S)-tetrahydro-5,8-dioxo-1H-[1,2,4]diazaphospholo[1,2-a]pyridazine-2,1,3(3H)-triyl])tetrakis(N-[(1S)-1-phenylethyl])benzamide; Bis[(S,S,S)-DiazaPhos-SPE]; 2,2′,2″,2′′′-(1,2-亚苯基双[(1S,3S)-四氢-5,8-二氧代-1H-[1,2,4]二氮杂磷杂环戊基[1,2-a]哒嗪-2,1,3(3H)-三基])四(N-[(1S)-1-苯乙基])苯甲酰胺

Database IDs

• CAS Number: 851770-14-4
• MDL Number: MFCD10566996
• PubChem SID: 162234928
• PubChem CID: 16160363

CALCULATED PROPERTIES

• Acid pKa: 14.302624
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 11.686199
• LogD (pH = 7.4): 11.6862
• Log P: 11.6862
• Molar Refractivity: 370.7514 cm^3
• Polarizability: 142.57104 Å^3
• Polar Surface Area: 197.64 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 289-299 °C
• Optical Rotation: [α]20/D +15.0°, c = 1 in THF

Product Information

• Empirical Formula (Hill Notation): C78H72N8O8P2

DETAILS

Sigma Aldrich - 685259

Application
Diazaphospholane ligands display excellent levels of conversion and selectivity in Rh-catalyzed asymmetric hydroformylation reactions.7,8
Diazaphospholane Ligands for Catalytic Asymmetric TransformationsCatalytic chiral bisdiazaphospholane ligand used for:
• Enantioselective synthesis of α,β-unsaturated aldehydes via hydroformylation of dienes catalyzed by rhodium catalyst1
• Stereoselective preparation of chiral aldehydes via rhodium-catalyzed enantioselective hydroformylation of N-vinyl carboxamides, allyl ethers, and allyl carbamates2
• Regioselective and enantioselective rhodium-catalyzed hydroformylation of styrene with (S,S,S)-bisdiazaphos3
• Regioselective and enantioselective hydroformylation of dialkyl acrylamides4
• Highly enantioselective hydroformylation of aryl alkenes5
• Styrene hydroformylation reactions catalyzed by rhodium(I) complexes of bis(phosphite) ligands6
Packaging
1 g in glass bottle
500 mg in glass bottle
Legal Information
Product is sold for R&D purpose only and use by end user in the manufacture of products of commerce is not permitted. Product is sold in association with DowpharmaSM a business unit of The Dow Chemical Company. U.S. Pat. 7,071,357B.