N,N-bis[(1R)-1-phenylethyl]-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosan-13-amine

• ChemBase ID: 140820
• Molecular Formular: C36H50NO2P
• Molecular Mass: 559.761461
• Monoisotopic Mass: 559.35791648
• SMILES: C[C@H](c1ccccc1)N([C@H](C)c1ccccc1)P1OC2CCC3CCCCC3C2C2C3CCCCC3CCC2O1
• Canonical SMILES: C[C@@H](N([C@@H](c1ccccc1)C)P1OC2CCC3C(C2C2C(O1)CCC1C2CCCC1)CCCC3)c1ccccc1
• InChI: InChI=1S/C36H50NO2P/c1-25(27-13-5-3-6-14-27)37(26(2)28-15-7-4-8-16-28)40-38-33-23-21-29-17-9-11-19-31(29)35(33)36-32-20-12-10-18-30(32)22-24-34(36)39-40/h3-8,13-16,25-26,29-36H,9-12,17-24H2,1-2H3/t25-,26-,29?,30?,31?,32?,33?,34?,35?,36?,40?/m1/s1
• InChIKey: PPLIGSFVBQXHMH-JBENKYBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-bis[(1R)-1-phenylethyl]-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,N-bis[(1R)-1-phenylethyl]-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,N-Bis[(1R)-1-phenylethyl]-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, (11bS); (S,R,R)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a′]dinaphthalen-4-yl)bis(1-phenylethyl)amine; (S,R,R)-(+)-(3,5-二氧杂-4-磷杂环庚二烯并[2,1-a:3,4-a′]二萘-4-基)二(1-苯基乙基)胺

Database IDs

• CAS Number: 415918-91-1
• MDL Number: MFCD08561138
• PubChem SID: 24884733; 162235060
• PubChem CID: 71310532

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 7.0366783
• LogD (pH = 7.4): 8.690011
• Log P: 9.4602
• Molar Refractivity: 165.8474 cm^3
• Polarizability: 66.14414 Å^3
• Polar Surface Area: 21.7 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 102-103 °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% (HPLC)
• Empirical Formula (Hill Notation): C36H30NO2P

DETAILS

Sigma Aldrich - 665363

Application
Chiral phosphoramidite ligand used in a highly enantioselective copper-catalyzed conjugate addition of diakylzincs to a variety of Michael acceptors.1,2,3 Also used in a palladium-catalyzed diethylzinc mediated umpolung allylation.4
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.