cyclohepta-2,4,6-trien-1-one

• ChemBase编号: 130046
• 分子式: C7H6O
• 平均质量: 106.12194
• 单一同位素质量: 106.04186481
• SMILES: O=c1cccccc1
• Canonical SMILES: O=c1cccccc1
• InChI: InChI=1S/C7H6O/c8-7-5-3-1-2-4-6-7/h1-6H
• InChIKey: QVWDCTQRORVHHT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: cyclohepta-2,4,6-trien-1-one
• IUPAC传统名: tropone
• 别名: 2,4,6-环庚三烯-1-酮; 环庚三烯酮; 2,4,6-Cycloheptatrien-1-one; Tropone; Tropone; Cycloheptatrienone

登记号

• CAS号: 539-80-0
• EC号: 208-725-6
• MDL号: MFCD00014331
• Beilstein号: 1902335
• PubChem SID: 24855242; 162224331
• PubChem CID: 10881
• Chemspider ID: 10419
• 维基百科标题: Tropone

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 1.3343216
• LogD (pH = 7.4): 1.3343216
• Log P: 1.3343216
• 摩尔折射率: 36.1516 cm^3
• 极化性: 12.250373 Å^3
• 极化表面积: 17.07 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

• 沸点: 113 °C (15 mmHg); 113 °C/15 mmHg(lit.); 91-92°C/4mm
• 闪点: >110°C(230°F); >113 °C; >235.4 °F
• 密度: 1.094; 1.094 g/mL; 1.094 g/mL at 25 °C(lit.)
• 折射率: 1.6150; n20/D 1.615(lit.)

安全信息

• 德国WGK号: 3
• TSCA收录: 否
• 个人保护装置: Eyeshields, Gloves
• 保存温度: -20°C

产品相关信息

• 纯度: 97%
• Empirical Formula (Hill Notation): C7H6O

详细说明

Sigma Aldrich - 252832

包装
1, 5 g in glass bottle

参考文献

• Reacts as a diene in the Diels-Alder reaction with electron-rich alkenes (inverse electron-demand); see, e.g.: Org. Synth. Coll., 9, 396 (1998):
  
• Alternatively, reaction can occur with electron-deficient alkenes, as exemplified by phenyl vinyl sulfoxide. In this case, cyclic elimination leads directly to bicyclo[3.2.2]nona-3,6,8-trien-2-one in low yield: J. Org. Chem., 48, 3591 (1983). For a review of cycloadducts of tropone and its analogs with sulfenes and ketenes, see: Heterocycles, 18, 343 (1982).
• For cycloaddition reactions with kinetically stabilized phosphaalkynes, leading to tetracyclic phosphorus-carbon cage compounds, see: J. Org. Chem., 60, 5884 (1995); Synthesis, 87 (1996).
• Reacts with Grignard reagents at the 2-position (1,6-addition) as in the first step of a synthesis of the hydroazulene skeleton: Tetrahedron Lett., 23, 1863 (1982). Addition of various Li enolates again leads to 2-substituted 2,6-dihydrotropones in good yield: J. Org. Chem., 53, 4596 (1988).