benzyl 2,5-dioxopyrrolidin-1-yl carbonate

• ChemBase编号: 149952
• 分子式: C12H11NO5
• 平均质量: 249.21944
• 单一同位素质量: 249.06372246
• SMILES: c1ccc(cc1)COC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)OCc1ccccc1
• InChI: InChI=1S/C12H11NO5/c14-10-6-7-11(15)13(10)18-12(16)17-8-9-4-2-1-3-5-9/h1-5H,6-8H2
• InChIKey: MJSHDCCLFGOEIK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: benzyl 2,5-dioxopyrrolidin-1-yl carbonate
• IUPAC传统名: benzyl 2,5-dioxopyrrolidin-1-yl carbonate
• 别名: 苄基 N-琥珀酰亚胺基碳酸酯; N-(苄氧羰基氧基)琥珀酰亚胺; N-(苄氧基羰基氧基)丁二酰亚胺; Z-OSu; Benzyl N-succinimidyl carbonate; N-(Benzyloxycarbonyloxy)succinimide; N-(Benzyloxycarbonyloxy)succinimide; Cbz-ONSu

登记号

• CAS号: 13139-17-8
• EC号: 236-075-3
• MDL号: MFCD00005513
• Beilstein号: 1387927
• PubChem SID: 24853653; 162244114
• PubChem CID: 83172

理论计算性质

• Acid pKa: 17.634148
• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 1.490004
• LogD (pH = 7.4): 1.490004
• Log P: 1.490004
• 摩尔折射率: 59.4337 cm^3
• 极化性: 23.493593 Å^3
• 极化表面积: 72.91 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: acetone: soluble0.1 g/mL, clear
• 熔点: 77-82°C; 78-81 °C; 80-82 °C(lit.)

安全信息

• 保存注意事项: Moisture Sensitive
• 德国WGK号: 3
• TSCA收录: 否
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95.0% (HPLC); 98%; 99%
• 级别: purum
• 燃烧残渣: ≤0.05%
• Empirical Formula (Hill Notation): C12H11NO5

详细说明

Sigma Aldrich - 227781

Application
用于向氨基酸1,2,3和氨基糖苷类抗生素4,5,6选择性引入 Z-氨基保护的试剂。
包装
25, 100, 250 g in poly bottle

Sigma Aldrich - 13631

Application
用于向氨基酸1,2,3和氨基糖苷类抗生素4,5,6选择性引入 Z-氨基保护的试剂。

参考文献

• Selective reagent for the introduction of the benzyloxycarbonyl (Cbz or Z) protecting group, avoiding the formation of amino acid dimers: Tetrahedron Lett., 4765 (1966); J. Antibiot., 25, 695 (1972); 34, 513 (1981); Can. J. Chem., 60, 976 (1982).
• Especially convenient for the selective protection of the -amino group of lysine and ornithine: Can. J. Chem., 54, 733 (1976); Rec. Trav. Chim.,99, 400 (1980). See Appendix 6.