(3Z)-4-[({[(2Z)-4-oxopent-2-en-2-yl]oxy}nickelio)oxy]pent-3-en-2-one

• ChemBase编号: 303070
• 分子式: C10H14NiO4
• 平均质量: 256.90916
• 单一同位素质量: 256.02455183
• SMILES: C/C(=C/C(=O)C)/O[Ni]O/C(=C\C(=O)C)/C
• Canonical SMILES: C/C(=C/C(=O)C)/O[Ni]O/C(=C\C(=O)C)/C
• InChI: InChI=1S/2C5H8O2.Ni/c2*1-4(6)3-5(2)7;/h2*3,6H,1-2H3;/q;;+2/p-2/b2*4-3-
• InChIKey: BMGNSKKZFQMGDH-FDGPNNRMSA-L

名称和登记号

名称

• IUPAC标准名: (3Z)-4-[({[(2Z)-4-oxopent-2-en-2-yl]oxy}nickelio)oxy]pent-3-en-2-one
• IUPAC传统名: (3Z)-4-[({[(2Z)-4-oxopent-2-en-2-yl]oxy}nickelio)oxy]pent-3-en-2-one
• 别名: 乙酰丙酮镍(II); Bis(acetylacetonato)nickel(II); Nickel(II) acetylacetonate; Nickel(II) 2,4-pentanedionate

登记号

• CAS号: 3264-82-2
• EC号: 221-875-7
• MDL号: MFCD00000024
• Beilstein号: 4157970
• 默克索引号: 146500

理论计算性质

• Acid pKa: 19.13614
• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): -0.0454
• LogD (pH = 7.4): -0.0454
• Log P: -0.0454
• 摩尔折射率: 54.8498 cm^3
• 极化性: 23.47894 Å^3
• 极化表面积: 52.6 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Soluble in water, alcohol, toluene
• 外观: Powder
• 熔点: ca 230°C dec.

安全信息

• 保存注意事项: Hygroscopic
• RTECS编号: SA2100000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 危险公开号: 49-22-43
• 安全公开号: 53-45
• TSCA收录: 是
• GHS危险品标识: GHS07; GHS08
• GHS危险声明: H350-H302-H317
• GHS警示性声明: P201-P308+P313

产品相关信息

• 纯度: 95%

参考文献

• Catalyst for a variety of coupling reactions, e.g.: Coupling of Grignard reagents to give biaryls: J. Org. Chem., 41, 2252 (1976). Coupling of Grignards with silyl enol ethers of both aldehydes and ketones, to give alkenes. In contrast to Dichlorobis(triphenylphosphine)nickel(II), 13930, this reagent gives the thermodynamically more stable alkene: Tetrahedron Lett., 3915 (1980). Cross-coupling of alkyl iodides with dialkylzinc reagents tolerates a variety of functionalities: Angew. Chem. Int. Ed., 34, 2723 (1995).
• Aryl phosphates couple with Grignards (aryl tosylates do not couple under these conditions), affording high yields of biaryls: Tetrahedron Lett., 22, 4449 (1981). Cross-coupling of aryl chlorides with arylzincs also yields biaryls: Tetrahedron Lett., 39, 6441, 7275 (1998).
• For use in the condensation of active methylene compounds with lactims, see Isopropylidene malonate, A15603.
• Catalyst for the conjugate addition of 1,3-dicarbonyl compounds to various Michael acceptors: J. Org. Chem., 45, 1246 (1980).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 1042 (2005).