2-[(2S)-2-{[(tert-butyldimethylsilyl)oxy]methyl}-3,4-dihydro-2H-pyrrol-5-yl]-2-[(5S)-5-{[(tert-butyldimethylsilyl)oxy]methyl}pyrrolidin-2-ylidene]acetonitrile

• ChemBase ID: 137932
• Molecular Formular: C24H45N3O2Si2
• Molecular Mass: 463.804
• Monoisotopic Mass: 463.30503076
• SMILES: CC(C)(C)[Si](C)(C)OC[C@@H]1CC/C(=C(/C#N)\C2=N[C@@H](CC2)CO[Si](C)(C)C(C)(C)C)/N1
• Canonical SMILES: N#C/C(=C\1/CC[C@H](N1)CO[Si](C(C)(C)C)(C)C)/C1=N[C@@H](CC1)CO[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C24H45N3O2Si2/c1-23(2,3)30(7,8)28-16-18-11-13-21(26-18)20(15-25)22-14-12-19(27-22)17-29-31(9,10)24(4,5)6/h18-19,26H,11-14,16-17H2,1-10H3/t18-,19-/m0/s1
• InChIKey: JYNLYWZVXIGLJC-OALUTQOASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S)-2-{[(tert-butyldimethylsilyl)oxy]methyl}-3,4-dihydro-2H-pyrrol-5-yl]-2-[(5S)-5-{[(tert-butyldimethylsilyl)oxy]methyl}pyrrolidin-2-ylidene]acetonitrile
• IUPAC Traditional name: 2-[(5S)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-4,5-dihydro-3H-pyrrol-2-yl]-2-[(5S)-5-{[(tert-butyldimethylsilyl)oxy]methyl}pyrrolidin-2-ylidene]acetonitrile
• Synonyms: (1S,9S)-1,9-Bis[(tert-butyldimethylsiloxy)methyl]-5-cyanosemicorrin; (1S,9S)-1,9-Bis[(tert-butyldimethylsiloxy)methyl]-5-cyanosemicorrin; Semicorrin chiral ligand 2; (1S,9S)-(-)-1,9-Bis[(tert-butyldimethylsilyloxy)methyl]-5-cyanosemicorrin; (1S,9S)-1,9-双[(叔丁基二甲基甲硅烷氧基)甲基]-5-氰基半咕啉; (1S,9S)-1,9-双[(叔丁基二甲基甲硅烷氧基)甲基]-5-氰基半咕啉; 半咕啉手性配体 2; (1S,9S)-(-)-1,9-双[(-叔丁基二甲基硅氧基)甲基]-5-氰基半咕啉

Database IDs

• CAS Number: 105251-52-3
• MDL Number: MFCD00142698
• Beilstein Number: 5153664
• PubChem SID: 24866340; 24848735; 162232192
• PubChem CID: 13704490

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.4024682
• LogD (pH = 7.4): 4.629612
• Log P: 4.7284
• Molar Refractivity: 124.3877 cm^3
• Polarizability: 52.187252 Å^3
• Polar Surface Area: 66.64 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 74-77 °C; 74-77 °C(lit.)
• Optical Rotation: [α]20/D -63±2°, c = 1% in chloroform; [α]20/D -64°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0%; 97%
• Empirical Formula (Hill Notation): C24H45N3O2Si2

DETAILS

Sigma Aldrich - 14556

Other Notes
The Cu(II) and Co(II) complexes are catalysts for enantioselective cyclopropanation and reduction reactions1,2
Packaging
10 mg in glass bottle

Sigma Aldrich - 420514

Application
Ligand for enantioselective catalysis.1,2,3