1-{[(tert-butoxy)carbonyl]amino}cyclopentane-1-carboxylic acid

• ChemBase ID: 38464
• Molecular Formular: C11H19NO4
• Molecular Mass: 229.27286
• Monoisotopic Mass: 229.13140809
• SMILES: C1(NC(=O)OC(C)(C)C)(C(=O)O)CCCC1
• Canonical SMILES: O=C(NC1(CCCC1)C(=O)O)OC(C)(C)C
• InChI: InChI=1S/C11H19NO4/c1-10(2,3)16-9(15)12-11(8(13)14)6-4-5-7-11/h4-7H2,1-3H3,(H,12,15)(H,13,14)
• InChIKey: YBZCSKVLXBOFSL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(tert-butoxy)carbonyl]amino}cyclopentane-1-carboxylic acid
• IUPAC Traditional name: 1-[(tert-butoxycarbonyl)amino]cyclopentane-1-carboxylic acid
• Synonyms: Boc-cycloleucine; 1-(Boc-amino)cyclopentanecarboxylic acid; Boc-1-aminocyclopentane-1-carboxylic acid; 1-{[(tert-butoxy)carbonyl]amino}cyclopentane-1-carboxylic acid; N-Boc-cycloleucine; N-tert-Butoxycarbonyl-1-aminocyclopentanecarboxylic acid; 1-((tert-Butoxycarbonyl)aMino)cyclopentanecarboxylic acid; Boc-Cycloleucine; Boc-环亮氨酸; 1-(Boc-氨基)环戊烷羧酸

Database IDs

• CAS Number: 35264-09-6
• EC Number: 000-000-0
• MDL Number: MFCD01076126
• Beilstein Number: 2734412
• PubChem SID: 24845516; 161001771
• PubChem CID: 2734645

CALCULATED PROPERTIES

• Acid pKa: 4.001885
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.41979864
• LogD (pH = 7.4): -1.2305171
• Log P: 1.9274708
• Molar Refractivity: 57.3294 cm^3
• Polarizability: 22.755922 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 129 - 131°C; 131-134°C
• Hydrophobicity(logP): 2.235

Safety Information

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

Product Information

• Purity: ≥98.0% (TLC); 95%; 98%
• Linear Formula: (CH3)3CO2CNHC5H8CO2H

DETAILS

Sigma Aldrich - 03583

Other Notes
This bulky cycloleucine imparts protection against hydrolysis to neighbouring amide bonds.1 Synthesis of conformationally restricted analogs.2