2-[(1S)-5,10-dioxo-2-phenyl-3-(2-{[(1S)-1-phenylethyl]carbamoyl}phenyl)-1H,2H,3H,5H,10H-[1,2,4]diazaphospholo[1,2-b]phthalazin-1-yl]-N-[(1S)-1-phenylethyl]benzamide

• ChemBase ID: 140686
• Molecular Formular: C46H39N4O4P
• Molecular Mass: 742.800021
• Monoisotopic Mass: 742.27089238
• SMILES: C[C@@H](c1ccccc1)NC(=O)c1ccccc1[C@H]1n2c(=O)c3ccccc3c(=O)n2C(P1c1ccccc1)c1ccccc1C(=O)N[C@@H](C)c1ccccc1
• Canonical SMILES: O=C(c1ccccc1C1P(c2ccccc2)[C@H](n2n1c(=O)c1ccccc1c2=O)c1ccccc1C(=O)N[C@H](c1ccccc1)C)N[C@H](c1ccccc1)C
• InChI: InChI=1S/C46H39N4O4P/c1-30(32-18-6-3-7-19-32)47-41(51)35-24-12-16-28-39(35)45-49-43(53)37-26-14-15-27-38(37)44(54)50(49)46(55(45)34-22-10-5-11-23-34)40-29-17-13-25-36(40)42(52)48-31(2)33-20-8-4-9-21-33/h3-31,45-46H,1-2H3,(H,47,51)(H,48,52)/t30-,31-,45-,46?,55?/m0/s1
• InChIKey: XLHCPIVFAWUOET-OQGDIVOVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S)-5,10-dioxo-2-phenyl-3-(2-{[(1S)-1-phenylethyl]carbamoyl}phenyl)-1H,2H,3H,5H,10H-[1,2,4]diazaphospholo[1,2-b]phthalazin-1-yl]-N-[(1S)-1-phenylethyl]benzamide
• IUPAC Traditional name: 2-[(1S)-5,10-dioxo-2-phenyl-3-(2-{[(1S)-1-phenylethyl]carbamoyl}phenyl)-1H,3H-[1,2,4]diazaphospholo[1,2-b]phthalazin-1-yl]-N-[(1S)-1-phenylethyl]benzamide
• Synonyms: (S,S,S)-DiazaPhos-PPE; 2,2′-[(1S,3S)-2,3,5,10-Tetrahydro-5,10-dioxo-2-phenyl-1H-[1,2,4]diazaphospholo[1,2-b]phthalazine-1,3-diyl]bis[N-(1S)-1-phenylethyl]benzamide; (S,S,S)-DiazaPhos-PPE; 2,2′-[(1S,3S)-2,3,5,10-四氢-5,10-二氧-2-苯基-1H-[1,2,4]二氮杂磷杂环戊烷[1,2-b]酞嗪-1,3-二基]双[N-(1S)-1-苯乙基]苯酰胺]

Database IDs

• CAS Number: 615538-63-1
• PubChem SID: 162234927
• PubChem CID: 71310491

CALCULATED PROPERTIES

• Acid pKa: 14.559948
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 8.3208
• LogD (pH = 7.4): 8.3208
• Log P: 8.3208
• Molar Refractivity: 215.4381 cm^3
• Polarizability: 81.92688 Å^3
• Polar Surface Area: 98.82 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 134-159 °C
• Optical Rotation: [α]20/D -27°, c = 1 in chloroform

Product Information

• Empirical Formula (Hill Notation): C46H39N4O4P

DETAILS

Sigma Aldrich - 685240

Application
Diazaphospholane ligands display excellent levels of conversion and selectivity in Rh-catalyzed asymmetric hydroformylation reactions.1,2
Diazaphospholane Ligands for Catalytic Asymmetric Transformations
Packaging
100, 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.