5,5-dimethylcyclohexane-1,3-dione

• ChemBase编号: 91841
• 分子式: C8H12O2
• 平均质量: 140.17968
• 单一同位素质量: 140.08372962
• SMILES: O=C1CC(=O)CC(C1)(C)C
• Canonical SMILES: O=C1CC(=O)CC(C1)(C)C
• InChI: InChI=1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3
• InChIKey: BADXJIPKFRBFOT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5,5-dimethylcyclohexane-1,3-dione
• IUPAC传统名: medon
• 别名: 双甲酮; 醛试剂; 5,5-二甲基-1,3-环己二酮; 双甲酮; Dimedone; Methone; 5,5-Dimethylcyclohexane-1,3-dione 98%; 5,5-Dimethyl-1,3-cyclohexanedione; DIMEDONE; 5,5-Dimethyl-1,3-cyclohexanedione; 5,5-dimethylcyclohexane-1,3-dione; Cyclomethone; Dimethyldihydroresorcinol; Dimedone

登记号

• CAS号: 126-81-8
• EC号: 204-804-4
• MDL号: MFCD00001588
• Beilstein号: 471489
• 默克索引号: 143242
• PubChem SID: 24864009; 24893475; 162078539
• PubChem CID: 31358
• Chemspider ID: 29091
• 维基百科标题: Dimedone

理论计算性质

• Acid pKa: 7.504177
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.4036998
• LogD (pH = 7.4): 1.156143
• Log P: 1.4079771
• 摩尔折射率: 37.9643 cm^3
• 极化性: 14.890126 Å^3
• 极化表面积: 34.14 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Yellow crystals
• 熔点: 142-151°C; 146-148 °C(lit.); 146-150°C; 146-151°C; 147–150 °C (decomposes)
• 沸点: 164-166°C

安全信息

• 保存条件: 2-8°C
• 保存注意事项: Irritant/Light Sensitive
• RTECS编号: GV0345000
• 德国WGK号: 2
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥99.0%; ≥99.0% (GC); 95%; 98%
• 级别: for HPLC derivatization
• 品质说明: for the determination of aldehyde formaldehyde
• 线性分子式: (CH3)2C6H6(=O)2

详细说明

MP Biomedicals - 02101594

Crystalline

Sigma Aldrich - D153303

Application
Furannulation 环化策略的一部分，用于合成天然稠合 3-甲基呋喃。1
包装
25, 100 g in poly bottle

参考文献

• Classical reagent for the identification and isolation of aldehydes: J. Org. Chem., 11, 95 (1946).
• A comparative study has shown that CAN is superior to Mn(OAc)₃ for this type of reaction: J. Chem. Soc., Perkin 1, 1487 (1996).
• For conditions leading to exclusive 2-monomethylation, see: Synth. Commun., 3, 347 (1973). For direct nitration at the 2-position, see review on ɑ-nitroketones: Synthesis, 261 (1980).
• Undergoes an example of an oxidative addition of 1,3-dicarbonyl compounds, mediated by CAN (Cerium(IV) ammonium nitrate, A12882), to give an alkene, e.g. with 2-methyl-2-pentene, the product is a fused dihydrofuran derivative: J. Chem. Soc., Perkin 1, 187 (1995):