(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane

• ChemBase ID: 130341
• Molecular Formular: C15H26N2
• Molecular Mass: 234.38034
• Monoisotopic Mass: 234.20959884
• SMILES: C1CCN2C[C@@H]3C[C@H]([C@H]2C1)CN1[C@H]3CCCC1
• Canonical SMILES: C1CC[C@@H]2N(C1)C[C@@H]1C[C@H]2CN2[C@@H]1CCCC2
• InChI: InChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m0/s1
• InChIKey: SLRCCWJSBJZJBV-ZQDZILKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^2,^7.0^1^0,^1^5]heptadecane
• IUPAC Traditional name: sparteine
• Synonyms: (6''R'',8''S'',10''R'',12''S'')-7,15-diazatetracyclo[7.7.1.0^2,7.0^10,15]heptadecane; Sparteine; (-)-Lupinidine; (-)-Sparteine; (-)-司巴丁; (-)-鹰爪豆碱

Database IDs

• CAS Number: 90-39-1
• EC Number: 201-988-8
• MDL Number: MFCD00069653
• PubChem SID: 162224620; 24865990
• PubChem CID: 644020
• CHEBI ID: 28827
• ATC CODE: C01BA04
• CHEMBL: 44625
• Chemspider ID: 559096
• DrugBank ID: DB06727
• KEGG ID: D01041
• Unique Ingredient Identifier: 298897D62S
• Wikipedia Title: Sparteine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -3.3671618
• LogD (pH = 7.4): -0.38936847
• Log P: 2.0278275
• Molar Refractivity: 71.823 cm^3
• Polarizability: 28.518066 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 137-138 °C/1 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 1.02 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.528(lit.)
• Optical Rotation: [α]20/D -16.5°, c = 10 in ethanol

Safety Information

• RTECS: WG5950000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 99%
• Empirical Formula (Hill Notation): C15H26N2

DETAILS

Sigma Aldrich - 415316

Application
Controls asymmetric lithiation/alkylation of prochiral diphenylmethanes1 and enantioselective deprotonation in preparation of chiral phosphine ligands.2
Organocatalyst compexed with copper (II) for the enantioselective syntheses of nitro aldols (Henry reaction).