N-benzyl-N-methyl-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosan-13-amine

• ChemBase ID: 140056
• Molecular Formular: C28H42NO2P
• Molecular Mass: 455.612341
• Monoisotopic Mass: 455.29531622
• SMILES: CN(Cc1ccccc1)P1OC2CCC3CCCCC3C2C2C3CCCCC3CCC2O1
• Canonical SMILES: CN(P1OC2CCC3C(C2C2C(O1)CCC1C2CCCC1)CCCC3)Cc1ccccc1
• InChI: InChI=1S/C28H42NO2P/c1-29(19-20-9-3-2-4-10-20)32-30-25-17-15-21-11-5-7-13-23(21)27(25)28-24-14-8-6-12-22(24)16-18-26(28)31-32/h2-4,9-10,21-28H,5-8,11-19H2,1H3
• InChIKey: UZKNLVXTVPLTJI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-benzyl-N-methyl-12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosan-13-amine
• IUPAC Traditional name: N-benzyl-N-methyl-12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosan-13-amine
• Synonyms: (+)-N-Benzyl-N-methyl-dinaphtho[2,1-d:1′,2′]dioxaphosphepin-4-amine, (11bS); (S)-(+)-Benzyl(3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a′]dinaphthalen-4-yl)methylamine; (+)-N-苄基-N-甲基-二萘并[2,1-d:1′,2′]二噁磷杂庚英-4-胺，(11bS); (S)-(+)-苄基(3,5-二氧杂-4-磷杂-环庚[2,1-a;3,4-a′]二萘-4-基)甲胺

Database IDs

• CAS Number: 490023-37-5
• MDL Number: MFCD04117686
• PubChem SID: 24884732; 162234300
• PubChem CID: 71310372

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.9455714
• LogD (pH = 7.4): 6.5406666
• Log P: 6.8574
• Molar Refractivity: 132.3972 cm^3
• Polarizability: 52.838528 Å^3
• Polar Surface Area: 21.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 155-159 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C28H22NO2P

DETAILS

Sigma Aldrich - 665355

Application
Phosphoramidite ligand used in a rhodium-catalyzed enantioselective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds.1 Also used in asymmetric hydrogenation of N-acylated β-dehydroamino esters to enantiopure β-amino acid derivatives.2
DSM MonoPhos Family of Highly Efficient Privileged Ligands
Packaging
100, 500 mg in glass bottle
2 g in glass bottle
Legal Information
Sold under license from DSM for research purposes only.