methyl (2S)-5-{cyano[(5S)-5-(methoxycarbonyl)pyrrolidin-2-ylidene]methyl}-3,4-dihydro-2H-pyrrole-2-carboxylate

• ChemBase ID: 156633
• Molecular Formular: C14H17N3O4
• Molecular Mass: 291.30248
• Monoisotopic Mass: 291.12190604
• SMILES: COC(=O)[C@@H]1CC/C(=C(/C#N)\C2=N[C@@H](CC2)C(=O)OC)/N1
• Canonical SMILES: COC(=O)[C@@H]1CC/C(=C(\C2=N[C@@H](CC2)C(=O)OC)/C#N)/N1
• InChI: InChI=1S/C14H17N3O4/c1-20-13(18)11-5-3-9(16-11)8(7-15)10-4-6-12(17-10)14(19)21-2/h11-12,16H,3-6H2,1-2H3/t11-,12-/m0/s1
• InChIKey: HEMMGWQVSFWCAQ-RYUDHWBXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-5-{cyano[(5S)-5-(methoxycarbonyl)pyrrolidin-2-ylidene]methyl}-3,4-dihydro-2H-pyrrole-2-carboxylate
• IUPAC Traditional name: methyl (2S)-5-{cyano[(5S)-5-(methoxycarbonyl)pyrrolidin-2-ylidene]methyl}-3,4-dihydro-2H-pyrrole-2-carboxylate
• Synonyms: Semicorrin chiral ligand 1; Dimethyl (1S,9S)-5-cyanosemicorrin-1,9-dicarboxylate; 半咕啉手性配体 1; (1S,9S)-5-氰基半咕啉-1,9-二羧酸二甲酯

Database IDs

• CAS Number: 105251-49-8
• MDL Number: MFCD00144132
• Beilstein Number: 5110296
• PubChem SID: 162250770; 24857227
• PubChem CID: 643219

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.10815498
• LogD (pH = 7.4): 0.13539658
• Log P: 0.13575518
• Molar Refractivity: 73.9645 cm^3
• Polarizability: 28.16242 Å^3
• Polar Surface Area: 100.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 77-79 °C; 77-79 °C(lit.)
• Optical Rotation: [α]20/D -145±2°, 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

Product Information

• Purity: ≥95.0% (sum of enantiomers, HPLC)
• Grade: purum
• Empirical Formula (Hill Notation): C14H17N3O4

DETAILS

Sigma Aldrich - 28600

Other Notes
Starting material for the preparation of various chiral bis(semicorrinato) Cu(II) and Co(II) catalysts1,2,3