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160407

Sigma-Aldrich

Dibenzyl malonate

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About This Item

Formula condensata:
CH2(CO2CH2C6H5)2
Numero CAS:
15014-25-2
Peso molecolare:
284.31
Beilstein:
1998264
Numero CE:
239-099-2
Numero MDL:
MFCD00004779
Codice UNSPSC:
12352100
ID PubChem:
24849869
NACRES:
NA.22

Forma fisica

liquid

Livello qualitativo

100

Indice di rifrazione

n20/D 1.546 (lit.)

P. eboll.

188 °C/0.2 mmHg (lit.)

Densità

1.137 g/mL at 25 °C (lit.)

Gruppo funzionale

ester
phenyl

Stringa SMILE

O=C(CC(=O)OCc1ccccc1)OCc2ccccc2

InChI

1S/C17H16O4/c18-16(20-12-14-7-3-1-4-8-14)11-17(19)21-13-15-9-5-2-6-10-15/h1-10H,11-13H2
RYFCSKVXWRJEOB-UHFFFAOYSA-N

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Descrizione generale

Direct asymmetric reaction of dibenzyl malonate with N-tert-butoxycarbonyl aldimines in the presence of Yb(OTf)3 and iPr-pybox (pybox = pyridine bisoxazoline) complexes has been investigated.

Applicazioni

Dibenzyl malonate was used in the preparation of tetraethyl 3,3-bis(benzyloxycarbonyl)propylene bisphosphonate. It was also used in the preparation of benzyl umbelliferone-3-carboxylate via Knoevenagel condensation with 2,4-dihydroxybezaldehyde.

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

230.0 °F - closed cup

Punto d’infiammabilità (°C)

110 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Certificati d'analisi (COA)

Lot/Batch Number
BGBC2103V
BGBC0651V
BGBB0047
MKAA3549
18406LH

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Babak Karimi et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 19(31), 10142-10145 (2013-06-22)
Go Mannich! A highly efficient and enantioselective method for the direct asymmetric reaction of dibenzyl malonate with N-tert-butoxycarbonyl aldimines in the presence of Yb(OTf)3 and iPr-pybox complexes is described (see scheme; pybox = pyridine bisoxazoline).
Synthesis of bone-targeted oestrogenic compounds for the inhibition of bone resorption.
Bulman Page PC, et al.
Tetrahedron, 57(9), 1837-1847 (2001)
J D Perry et al.
Journal of applied microbiology, 101(5), 977-985 (2006-10-17)
Enzyme substrates based on 4-methylumbelliferone are widely used for the detection of Escherichia coli and enterococci in water, by detection of beta-glucuronidase and beta-glucosidase activity respectively. This study aimed to synthesize and evaluate novel umbelliferone-based substrates with improved sensitivity for
Prerana D Tomke et al.
Ultrasonics sonochemistry, 38, 496-502 (2017-06-22)
Poly (ethylene glutarate), poly (ethylene malonate) and poly (ethylene phthalate), were enzymatically synthesized by immobilized Candida antarctica lipase B in solvent free conditions. The synthesis of these polyesters was based on the ester-ester exchange reaction between ethylene glycol diacetate and
Riin Rebane et al.
Journal of chromatography. A, 1390, 62-70 (2015-03-12)
Derivatization is one of the most common ways for improving chromatographic separation and sensitivity for LC-ESI-MS analysis. The aim of this work was to design new derivatization reagents for LC-ESI-MS analysis of amino acids which would (1) provide good reversed

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