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Merck
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文件

210145

Sigma-Aldrich

2,2-二甲基-1,3-二噁烷-4,6-二酮

98%

别名:

丙二酸亚异丙酯, 丙二酸环亚异丙酯, 米氏酸

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About This Item

经验公式（希尔记法）:
C6H8O4
CAS号:
2033-24-1
分子量:
144.13
Beilstein:
117310
EC號碼:
217-992-8
MDL號碼:
MFCD00006638
分類程式碼代碼:
12352100
PubChem物質ID:
24852618
NACRES:
NA.22

化驗

98%

形狀

solid

mp

92-96 °C (lit.)

溶解度

dioxane: soluble 5%, clear to very slightly hazy, colorless to faintly yellow

儲存溫度

2-8°C

SMILES 字串

CC1(C)OC(=O)CC(=O)O1

InChI

1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3

InChI 密鑰

GXHFUVWIGNLZSC-UHFFFAOYSA-N

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相关类别

一般說明

2,2-二甲基-1,3-二恶烷-4,6-二酮（米氏′酸）广泛用于有机合成，特别是对于多种CC键形成，因为它具有足够的酸性 (pKa 4.83) 和空间刚性。醛与米氏′酸之间的Knoevenagel缩合反应在离子液体中加速。

米氏′酸被用作合成杂环的有价值的起始原料和有机合成反应的中间体。

應用

2,2-二甲基-1,3-二恶烷-4,6-二酮用于合成：
  • 大环 β-酮内酯
  • 4-吡啶基取代的杂环
  • 2-取代吲哚
  • 异秦皮啶。

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 2

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

Eyeshields, Gloves, type N95 (US)

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1,3-二甲基巴比妥酸 ≥99.0% (T)

Sigma-Aldrich

39565

1,3-二甲基巴比妥酸

Aaron M Dumas et al.
Accounts of chemical research, 43(3), 440-454 (2009-12-17)
Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) is a molecule with a unique history, owing to its originally misassigned structure, as well as a unique place among acylating agents, owing to its high acidity and remarkable electrophilicity. In this Account, we outline the work
Songlei Zhu et al.
Molecules (Basel, Switzerland), 17(12), 13856-13863 (2012-11-24)
A series of 4-aryl-6-methyl-3,4-dihydro-2H-pyrano[3,2-c]quinolin-2,5(6H)-diones were synthesized via the three-component reactions of aromatic aldehydes, 4-hydroxy-1-methylquinolin-2(1H)-one, and Meldrum's acid catalyzed by L-proline. The structures of the products were identified by spectroscopic analysis. A mechanism for this three-component reaction catalyzed by L-proline was
Davood Nematollahi et al.
Chemical & pharmaceutical bulletin, 58(1), 23-26 (2010-01-05)
Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile in aqueous solution has been studied in detail by means of cyclic voltammetry and controlled potential coulometry. The results indicate that the o-benzoquinone derived from catechols participates
The synthesis of β-keto lactones via cyclization of β-keto ester dianions or the cyclization of Meldrum's acid derivatives.
Lermer L, et al.
Canadian Journal of Chemistry, 70(5), 1427-1445 (1992)
New multicomponent domino reactions (MDRs) in water: highly chemo-, regio-and stereoselective synthesis of spiro {[1, 3] dioxanopyridine}-4, 6-diones and pyrazolo [3, 4-b] pyridines.
Ma N, et al.
Green Chemistry, 12?(8), 1357-1361 (2010)
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Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

Knoevenagel Condensation Reaction

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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