(5S)-5-benzyl-6,6-dimethyl-2-(2,4,6-trimethylphenyl)-5H,6H,8H-7,1,2λ5,4-[1λ5,2,4]triazolo[3,4-c][1,4]oxazin-2-ylium; tetrafluoroboranuide

• ChemBase ID: 142855
• Molecular Formular: C23H28BF4N3O
• Molecular Mass: 449.2925328
• Monoisotopic Mass: 449.22615581
• SMILES: [B-](F)(F)(F)F.Cc1cc(c(c(c1)C)[n+]1cn2c(n1)COC([C@@H]2Cc1ccccc1)(C)C)C
• Canonical SMILES: F[B-](F)(F)F.Cc1cc(C)c(c(c1)C)[n+]1cn2c(n1)COC([C@@H]2Cc1ccccc1)(C)C
• InChI: InChI=1S/C23H28N3O.BF4/c1-16-11-17(2)22(18(3)12-16)26-15-25-20(13-19-9-7-6-8-10-19)23(4,5)27-14-21(25)24-26;2-1(3,4)5/h6-12,15,20H,13-14H2,1-5H3;/q+1;-1/t20-;/m0./s1
• InChIKey: PVYSZYZMWZCJCT-BDQAORGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-5-benzyl-6,6-dimethyl-2-(2,4,6-trimethylphenyl)-5H,6H,8H-7,1,2λ^5,4-[1λ^5,2,4]triazolo[3,4-c][1,4]oxazin-2-ylium; tetrafluoroboranuide
• IUPAC Traditional name: (5S)-5-benzyl-6,6-dimethyl-2-(2,4,6-trimethylphenyl)-5H,8H-7,1,2λ^5,4-[1λ^5,2,4]triazolo[3,4-c][1,4]oxazin-2-ylium tetrafluoroborate
• Synonyms: (S)-5-Benzyl-2-mesityl-6,6-dimethyl-6,8-dihydro-5H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate; (S)-5-苄基-2-均三甲苯基-6,6-二甲基-6,8-二氢-5H-[1,2,4]三氮唑并[3,4-c][1,4]噁嗪-2-四氟硼酸鎓盐

Database IDs

• CAS Number: 925706-40-7
• PubChem SID: 162237081
• PubChem CID: 71310800

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.9011757
• LogD (pH = 7.4): 2.9011757
• Log P: 2.9011757
• Molar Refractivity: 110.0553 cm^3
• Polarizability: 42.523643 Å^3
• Polar Surface Area: 30.93 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 200-206 °C
• Optical Rotation: [α]/D -117.8°, c = 0.5 in chloroform

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C23H28BF4N3O

DETAILS

Sigma Aldrich - 708569

Packaging
100, 500 mg in glass bottle
Application
Catalyst for:
• Intermolecular conjugate addition of alcohols to unsaturated ketones and esters1
• Preparation of β-amino carbonyl compounds by N-heterocyclic carbene-catalyzed enantioselective Mannich reactions of a-aryloxyacetaldehydes with imines2
• Asymmetric synthesis of cyclopentenes from allyl diketones by carbene-catalyzed intramolecular aldol reaction, lactonization, and carbon dioxide expulsion3
• Preparation of esters via tandem oxidation of allylic/benzylic/propargyl alcohols or aldehyde4