(3R,7aS)-3-(trichloromethyl)-hexahydropyrrolo[1,2-c][1,3]oxazol-1-one

• ChemBase ID: 142791
• Molecular Formular: C7H8Cl3NO2
• Molecular Mass: 244.50292
• Monoisotopic Mass: 242.96206154
• SMILES: C1C[C@H]2C(=O)O[C@@H](N2C1)C(Cl)(Cl)Cl
• Canonical SMILES: O=C1O[C@@H](N2[C@H]1CCC2)C(Cl)(Cl)Cl
• InChI: InChI=1S/C7H8Cl3NO2/c8-7(9,10)6-11-3-1-2-4(11)5(12)13-6/h4,6H,1-3H2/t4-,6+/m0/s1
• InChIKey: GWQBXRYSVSZLSL-UJURSFKZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,7aS)-3-(trichloromethyl)-hexahydropyrrolo[1,2-c][1,3]oxazol-1-one
• IUPAC Traditional name: (3R,7aS)-3-(trichloromethyl)-tetrahydro-3H-pyrrolo[1,2-c][1,3]oxazol-1-one
• Synonyms: (3R-cis)-Tetrahydro-3-(trichloromethyl)-1H,3H-pyrrolo[1,2-c]oxazol-1-one; L-Proline - chloral condensation product; (2R,5S)-2-Trichloromethyl-3-oxa-1-azabicyclo[3.3.0]octan-4-one; (2R,5S)-2-Trichloromethyl-3-oxa-1-azabicyclo[3.3.0]octan-4-one; L-Proline-chloral condensation product; (3R-cis)-Tetrahydro-3-trichloromethyl-1H,3H-pyrrolo[1,2-c]oxazol-1-one; (3R-顺)-四氢-3-(三氯甲基)-1H,3H-吡咯并[1,2-c]噁唑-1-酮; L-脯氨酸-三氯乙醛缩合产物; (2R,5S)-2-三氯甲基-3-氧-1-氮杂双环[3.3.0]辛-4-酮; (3R-顺式)-四氢-3-三氯甲基--1H,3H-吡咯[1,2-c]恶唑-1-酮

Database IDs

• CAS Number: 97538-67-5
• MDL Number: MFCD08274464
• PubChem SID: 24866374; 162237017
• PubChem CID: 10944680

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.1613097
• LogD (pH = 7.4): 2.1613097
• Log P: 2.1613097
• Molar Refractivity: 50.8512 cm^3
• Polarizability: 20.25663 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 108-112 °C; 109°C dec.
• Optical Rotation: [α]/D 29 to 34°, c = 2 in toluene; -2.9 (c= 1 in chloroform)

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (AT); 98%
• Empirical Formula (Hill Notation): C7H8Cl3NO2

DETAILS

Sigma Aldrich - 42134

Application
Valuable precursor to enantiomerically pure C- and N-protected α-alkyl prolines1.
Packaging
1 g in poly tube
5 g in poly bottle