tert-butyl N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]carbamate

• ChemBase ID: 162506
• Molecular Formular: C11H16N2O4
• Molecular Mass: 240.25574
• Monoisotopic Mass: 240.111007
• SMILES: C1=CC(=O)N(C1=O)CCNC(=O)OC(C)(C)C
• Canonical SMILES: O=C(OC(C)(C)C)NCCN1C(=O)C=CC1=O
• InChI: InChI=1S/C11H16N2O4/c1-11(2,3)17-10(16)12-6-7-13-8(14)4-5-9(13)15/h4-5H,6-7H2,1-3H3,(H,12,16)
• InChIKey: SNYRFQCLCLMCCG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]carbamate
• IUPAC Traditional name: tert-butyl N-[2-(2,5-dioxopyrrol-1-yl)ethyl]carbamate
• Synonyms: N-[2-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethyl]carbamic Acid 1,1-Dimethylethyl Ester; N-(2-Boc-amino)ethyl Maleimide

Database IDs

• CAS Number: 134272-63-2
• PubChem SID: 162256641
• PubChem CID: 4176840

CALCULATED PROPERTIES

• Acid pKa: 14.767236
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.2828867
• LogD (pH = 7.4): 0.2828867
• Log P: 0.2828867
• Molar Refractivity: 61.0709 cm^3
• Polarizability: 23.30055 Å^3
• Polar Surface Area: 75.71 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Crystalline Solid
• Melting Point: 110-115°C

DETAILS

Toronto Research Chemicals - B618750

It is used in the Mitsunobu reaction: a novel method for the synthesis of bifunctional maleimide linkers.

REFERENCES

• Antczak, C., et al.: Bioorg. Med. Chem., 9, 2843 (2001)