1-{12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosan-13-yl}piperidine

• ChemBase ID: 140058
• Molecular Formular: C25H42NO2P
• Molecular Mass: 419.580241
• Monoisotopic Mass: 419.29531622
• SMILES: C1CCC2C(C1)CCC1C2C2C3CCCCC3CCC2OP(O1)N1CCCCC1
• Canonical SMILES: C1CCN(CC1)P1OC2CCC3C(C2C2C(O1)CCC1C2CCCC1)CCCC3
• InChI: InChI=1S/C25H42NO2P/c1-6-16-26(17-7-1)29-27-22-14-12-18-8-2-4-10-20(18)24(22)25-21-11-5-3-9-19(21)13-15-23(25)28-29/h18-25H,1-17H2
• InChIKey: LNSRHQBBAYBXNN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosan-13-yl}piperidine
• IUPAC Traditional name: 1-{12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosan-13-yl}piperidine
• Synonyms: (S)-PipPhos; (S)-(+)-4-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-piperidine; (S)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a′]dinaphthalen-4-yl)piperidine; (S)-(+)-4-二萘并[2,1-d:1′,2′-f][1,3,2]二噁磷杂庚英-4-基-哌啶; (S)-(+)-(3,5-二氧杂-4-磷杂环庚二烯并[2,1-a:3,4-a′]二萘-4-基)哌啶

Database IDs

• MDL Number: MFCD08276865
• PubChem SID: 162234302; 24884739
• PubChem CID: 70700385

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.3670497
• LogD (pH = 7.4): 5.0951943
• Log P: 5.8027
• Molar Refractivity: 119.9266 cm^3
• Polarizability: 48.031612 Å^3
• Polar Surface Area: 21.7 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 206-213 °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): C25H22NO2P

DETAILS

Sigma Aldrich - 665479

Application
Asymmetric hydrogenation of N-aryl imines1
Phosphoramidite ligand used in a rhodium-catalyzed enantioselective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds.
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.