2,2-dimethyl-1,3-dioxane-4,6-dione

• ChemBase编号: 58237
• 分子式: C6H8O4
• 平均质量: 144.12532
• 单一同位素质量: 144.04225874
• SMILES: C1(=O)OC(OC(=O)C1)(C)C
• Canonical SMILES: O=C1CC(=O)OC(O1)(C)C
• InChI: InChI=1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3
• InChIKey: GXHFUVWIGNLZSC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2,2-dimethyl-1,3-dioxane-4,6-dione
• IUPAC传统名: meldrum's acid
• 别名: 丙二酸亚异丙酯; 丙二酸环亚异丙酯; 米氏酸; 2,2-二甲基-1,3-二噁烷-4,6-二酮; 丙二酸亚异丙酯; 2,2-Dimethyl-1,3-dioxane-4,6-dione; Meldrum’s acid; Malonic acid cyclic isopropylidene ester; cycl-Isopropylidene malonate; 2,2-Dimethyl-1,3-dioxane-4,6-dione; 2,2-Dimethyl-1,3-dioxane-4,6-dione; 2,2-Propanediol Cyclic Malonate; Cyclic Isopropylidene Malonate; Isopropylidene Malonate; Meldrumic Acid; NSC 688343; NSC 71902; Meldrum's acid; Meldrum's Acid; Isopropylidene malonate

登记号

• CAS号: 2033-24-1
• EC号: 217-992-8
• MDL号: MFCD00006638
• Beilstein号: 117310
• 默克索引号: 145817
• PubChem SID: 24852618; 162063000
• PubChem CID: 16249
• Chemspider ID: 15418
• 维基百科标题: Meldrum's_acid

理论计算性质

• Acid pKa: 10.625212
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 0.3768392
• LogD (pH = 7.4): 0.37658447
• Log P: 0.37684244
• 摩尔折射率: 31.2306 cm^3
• 极化性: 12.73627 Å^3
• 极化表面积: 52.6 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

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 89-91°C; 92-96 °C(lit.); 92-96°C; 92-96°C; 94–95 °C (decomposes)
• pKa: 4.97

安全信息

• 保存条件: Refrigerator
• 保存注意事项: IRRITANT; Irritant/Keep Cold
• RTECS编号: JH0800000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-37
• TSCA收录: false; 是
• GHS危险品标识: GHS07
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 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+%; 97%; 98%
• Empirical Formula (Hill Notation): C6H8O4

详细说明

Sigma Aldrich - 210145

Application
可通过与三乙基碳酸氢铵发生羟醛缩合反应和还原反应而制得苄基取代的米氏酸，1该物质经水解失去 CO2，同时与氯磺酸发生 Friedel-Crafts 环化反应形成茚酮。2可在离子液体中加速醛和米氏酸的 Knoevenagel 缩合反应。3
用于异嗪皮啶的高效合成。
包装
10, 25, 100 g in glass bottle

Toronto Research Chemicals - M215250

An antimicrobial agent of deodorant composition. Bactericides, disinfectants, and antiseptics.

参考文献

• Nelson, N., et al.: J. Biol. Chem., 245, 143 (1970)
• Kawamura, M., et al.: Plant Cell Physiol., 21, 745 (1970)
• Oettmeier, W., et al.: Biochim. Biophys Acta, 890, 260 (1970)
• See also: Org. Synth., 77, 114 (1999).
• Condensation with lactim ethers, catalyzed by Nickel(II) 2,4-pentanedionate, 18811, with alcoholysis of the resulting enamino Meldrum's acids, gives of cyclic ?-enamino esters, useful as alkaloid precursors: J. Org. Chem., 43, 4662 (1978); for an example, see: Org. Synth. Coll., 8, 263 (1993).
• Malonate ester which is an unusually strong acid (pK_a = 9.97) in comparison with, e.g. Diethyl malonate, A15468: J. Am. Chem. Soc., 70, 3426 (1948). The mild conditions required for alkylation, acylation, etc. and the ease with which the products undergo alcoholysis or hydrolysis-decarboxylation make Meldrum's acid a valuable and versatile synthetic intermediate. Reviews: Chem. Soc. Rev., 7, 345 (1978); Heterocycles, 32, 529 (1991); Synlett, 1649 (2004).
• For phase-transfer alkylation using K₂CO₃ as base, see: Synthesis, 452 (1982); Bull. Soc. Chim. Belg., 104, 643 (1995). Phase-transfer addition to Michael acceptors also occurs: Synthesis, 224 (1984). Mitsunobu dialkylation with an alcohol and DIAD/Ph₃P is also possible: J. Org. Chem., 62, 1617 (1997).
• Knoevenagel condensation with aldehydes gives ylidene derivatives which are solvolyzed by alcohols to give monoesters of alkylidene or arylidene malonic acids: J. Am. Chem. Soc., 74, 5897 (1952). For diastereoselective condensation with citronellal, followed by intramolecular Diels-Alder reaction, see: Org. Synth. Coll., 8, 353 (1993). With formaldehyde in pyridine gives the stable pyridinium methylide which, on treatment with acid, generates the useful reactive Michael acceptor and dienophile, methylene Meldrum's acid: Synthesis, 215 (1996).
• With an aryl aldehyde in the presence of triethylamine and formic acid at ambient temperature, in situ reduction to the arylmethyl Meldrum's acid occurs, whereas at 70-80^oC, the 3-arylpropionic acid is obtained: Synth. Commun., 25, 3067 (1995).
• C-Acylation with acyl chlorides occurs in the presence of 2 equivalents of pyridine in high yield. Alcoholysis of the product provides a good route to ?-keto esters: J. Org. Chem., 43, 2087 (1978); Org. Synth. Coll.,7, 359 (1988), also obtainable by reaction of the Na salt with acid anhydrides in DMF: Synthesis, 451 (1982). Alternatively, mild hydrolysis and decarboxylation of the intermediate acyl Meldrum's acid gives the methyl ketone, providing an alternative to organometallic methods for conversion of acyl chlorides to methyl ketones: Synth. Commun., 10, 221 (1980):