4-amino-1-[(2R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

• ChemBase编号: 168055
• 分子式: C9H11F2N3O4
• 平均质量: 263.1981464
• 单一同位素质量: 263.07176229
• SMILES: n1c(=O)n(ccc1N)[C@H]1C(C(O)[C@@H](CO)O1)(F)F
• Canonical SMILES: OC[C@H]1O[C@H](C(C1O)(F)F)n1ccc(nc1=O)N
• InChI: InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6?,7-/m1/s1
• InChIKey: SDUQYLNIPVEERB-ZJXFTUPMSA-N

名称和登记号

名称

• IUPAC标准名: 4-amino-1-[(2R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
• IUPAC传统名: 4-amino-1-[(2R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• 别名: 4-Amino-1-(deoxy-2,2-difluoro-D-threo-pentofuranosyl)-2(1H)-pyrimidinone; (Gemcitabine Impurity; 3'-Epi Gemcitabine (Gemcitabine Impurity)

登记号

• CAS号: 103882-85-5
• PubChem SID: 162262187
• PubChem CID: 46705350

理论计算性质

• Acid pKa: 11.51707
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): -1.4665402
• LogD (pH = 7.4): -1.4665728
• Log P: -1.4665396
• 摩尔折射率: 53.2503 cm^3
• 极化性: 20.563793 Å^3
• 极化表面积: 108.38 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Methanol
• 外观: White Solid
• 熔点: 102-104°C

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - E588520

An impurity from the synthesis of Gemcitabine.

参考文献

• Haufman, et al.: Science, 145, 585 (1964)
• Prusoff, et al.: Biochim. Biophys. Acta, 32, 295 (1959)