2,5-dioxopyrrolidin-1-yl 6-[(4-azido-2-nitrophenyl)amino]hexanoate

• ChemBase ID: 133589
• Molecular Formular: C16H18N6O6
• Molecular Mass: 390.35072
• Monoisotopic Mass: 390.12878233
• SMILES: c1cc(c(cc1N=[N+]=[N-])[N+](=O)[O-])NCCCCCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: [N-]=[N+]=Nc1ccc(c(c1)[N+](=O)[O-])NCCCCCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C16H18N6O6/c17-20-19-11-5-6-12(13(10-11)22(26)27)18-9-3-1-2-4-16(25)28-21-14(23)7-8-15(21)24/h5-6,10,18H,1-4,7-9H2
• InChIKey: NGXDNMNOQDVTRL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 6-[(4-azido-2-nitrophenyl)amino]hexanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 6-[(4-azido-2-nitrophenyl)amino]hexanoate
• Synonyms: 6-(4-Azido-2-nitrophenylamino)hexanoic acid N-hydroxysuccinimide ester; N-琥珀酰亚胺基-6-(4-叠氮-2-硝基苯胺基)己酸酯; 6-(4-叠氮-2-硝基苯胺基)己酸 N-羟基琥珀酰亚胺酯

Database IDs

• CAS Number: 64309-05-3
• MDL Number: MFCD00049058
• PubChem SID: 162227866; 24890767
• PubChem CID: 3035550

CALCULATED PROPERTIES

• Acid pKa: 15.10757
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 2.604712
• LogD (pH = 7.4): 2.604712
• Log P: 2.7187576
• Molar Refractivity: 99.1589 cm^3
• Polarizability: 35.5672 Å^3
• Polar Surface Area: 150.96 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; ethyl acetate: soluble10 mg/mL
• Apperance: orange powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥85%

DETAILS

Sigma Aldrich - A3407

Application
具有延长间隔的光敏、双异官能化交联剂。通常情况下，初始反应通过在 6.5 至 8.5 的 pH 范围内形成酰胺键将酯连接至伯胺。紫外光 (250-350nm) 照射的过程中通过激活氮宾发生二次键合。后一次键合快速并且具有非特异性。
Caution
还原剂（如硫醇）可将叠氮化合物还原为胺，因此应当避免还原剂出现在反应中。初始操作和偶联应当在弱光照条件下进行。
Other Notes
需要注意的是，相比简单的芳基叠氮化合物，硝基取代基提供的吸收谱带波长更长。