2,2-Dimethyl-1,3-dioxane-4,6-dione 丙二酸环(亚)异丙酯

CAS 2033-24-1 MFCD00006638

化学结构图

2033-24-1
SMILES: CC1(C)OC(=O)CC(=O)O1

化学属性

Mol. FormulaC6H8O4
Mol. Weight144.13
Density1.201
Melting Point92-96°C
TSCAYes
Solubility2.5 G/100 ML (20 ºC)
Appearance 白色结晶。熔点94-95℃,水溶性 2.5g/100ml(20℃)
Boiling Point356.7°C at 760 mmHg

别名和识别编码

Chemical Name2,2-Dimethyl-1,3-dioxane-4,6-dione
CAS Number2033-24-1
Alfabeta NameDIMETHYLDIOXANEDIONE 221346-----,,,
MDL NumberMFCD00006638
Synonym Meldrum's acid {LY} Meldrum's acid {} {LY} Meldrum's acid {} {} {LY} Meldrum's acid {} {} {} {LY} Meldrum's acid {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {} {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Meldrum's acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {}
EC Number217-992-8
Beilstein Registry Number117310
Merck Number5817
PubChem Substance ID16249
Reaxys-RN117310
Chemical Name Translation丙二酸环(亚)异丙酯
Wiswesser Line NotationT6OV DVOTJ F1 F1
LabNetwork Molecule IDLN00009658
InChIInChI=1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3
Canonical SMILESO=C(C1)OC(C)(C)OC1=O
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分类

  • Pharmaceuticals
  • {SNA} Building Blocks, Carbonyl Compounds, Chemical Synthesis, Lactones, Organic Building Blocks
  • Heterocycles
  • Intermediates & Fine Chemicals
  • {uni_hamburg} no charge; oxygen heterocycle; alicycle; 6RingOnly; 6ring; ester; lactone; acetal; 1fragment

产品应用

  • 通过羟醛冷凝和用三乙基胺甲醛还原得到,苄基取代的米氏酸经由水解、失去CO2和氯磺酸进行Friedel-Crafts 环化生成2,3-二氢-2-茚酮。离子液体中加速醛和米氏酸之间的诺文葛尔浓缩反应(Knoevenagel condensations)。

相关文献及参考

  • 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 ß-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):
  • 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 conde
  • 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
  • Merck:14,5817
  • 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).
  • Nelson, N., et al.: J. Biol. Chem., 245, 143
  • Condensation with lactim ethers, catalyzed by Nickel(II)­ 2,4-pentanedionate, 18811, with alcoholysis of the resulting enamino Meldrum's acids, gives of cyclic ß-enamino esters, useful as alkaloid precursors: J. Org. Chem., 43, 4662 (1978); for an example, see: Org. Synth. Coll., 8, 263 (1993).
  • Merck:14,5817 Beilstein: 19,V,5,8

安全信息

Warnings IRRITANT
Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛,皮肤或衣服。
RTECSJH0800000
Hazard Codes Xi
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Storage condition 2-8°C {LY} 2-8°C Store at room temperature {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 180 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems
   Laboratory, NIOSH Exchange Chemicals.  (Aberdeen Proving Ground, MD 21010)
   Volume(issue)/page/year: NX#04102

其他信息

  • Sigma Aldrich:2033-24-1(sigmaaldrich)
  • 方法一:在搅拌下,将浓硫酸加入丙二酸与乙酐组成的悬浮液中。待大部分丙二酸溶解后,冷却,保持温度为20-25℃,向反应物中加入丙酮,搅匀,冷却过夜,滤出析晶,用冰水洗涤,干燥,得2,2-二甲基-1,3二噁烷-4,6-二酮。
  • 图谱信息:丙二酸环(亚)异丙酯(2033-24-1)质谱(MS) 丙二酸环(亚)异丙酯(2033-24-1)核磁图( 13 CNMR) 丙二酸环(亚)异丙酯(2033-24-1)红外图谱(IR1) 丙二酸环(亚)异丙酯(2033-24-1)红外图谱(IR2)
  • MSDS 信息:2,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1).msds
  • 上游原料:丙二酸
  • 用途一:用作医药中间体
  • Alfa Aesar:丙二酸亚异丙酯,98% Isopropylidene malonate, 98%(2033-24-1)
  • TCI Shanghai:米氏酸(丙二酸环亚异丙酯) Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione),>;98.0%(T)(2033-24-1)
  • 下游产品:喹啉-4-硼酸 --> 喹啉-4-羧酸 --> 6-溴-4-氯喹啉 --> 4-溴喹啉 --> 4-氯喹啉 --> 4,7-二甲氧基-1,10-菲咯啉 --> 7-二乙基氨基-3-噻吩甲酰基香豆素 --> 3-(4-硝基苯基)丙酸 --> 6-溴喹啉-4(3H)-酮 --> 3-(2-噻吩)丙酸 --> 3-(4-硝基苯基)-1-丙醇
  • 用途二:用于有机合成。
  • 丙二酸环(亚)异丙酯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/04/16 M0799 米氏酸(=2,2-二甲基-1,3-二氧六环-4,6-二酮) Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione) 100G 1180元 2011/04/16 M0799 米氏酸(=2,2-二甲基-1,3-二氧六环-4,6-二酮) Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione) 25G 400元 2011/04/16 M0799 米氏酸(=2,2-二甲基-1,3-二氧六环-4,6-二酮) Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione) 500G 4050元
  • 存储注意事项:氮气保护
  • Acros Organics:2,2-二甲基-1,3-二恶烷-4,6-二酮 2,2-Dimethyl-1,3-dioxane-4,6-dione, 98%(2033-24-1)
  • F:10-21
  • 水中溶解: 2.5 G/100 ML (20°C),微溶于乙醇和氯仿。
  • 丙二酸环(亚)异丙酯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 M0799 米氏酸(=2,2-二甲基-1,3-二氧六环-4,6-二酮) Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione) 100G 335元 2014/06/02 M0799 米氏酸(=2,2-二甲基-1,3-二氧六环-4,6-二酮) Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione) 25G 112元 2014/06/02 M0799 米氏酸(=2,2-二甲基-1,3-二氧六环-4,6-二酮) Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione) 500G 990元
  • MOL 文件:2033-24-1.mol

系列性分类


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