5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Name: 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione
Brand: ChemScene
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CAS No. 15568-85-1
Cat. No. CS-M0456
Purity≥95%
MDL No.MFCD00599240

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FedEx Limited Quantities Ground	$0.00
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5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione|CS-M0456

Structure of 15568-85-1

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General Information

CAS No. 15568-85-1
Cat. No. CS-M0456
Purity ≥95%
MDL No. MFCD00599240
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₀O₅
Molecular Weight 186.16
Synonym(s) Methoxymethylene meldrum's acid
SMILES O=C(/C1=C\OC)OC(C)(C)OC1=O

Description

This dioxane derivative features a methoxymethylene group flanking a sterically hindered 1,3-dioxane core, enabling stable integration into complex syntheses. The electron-deficient carbonyl system supports efficient Michael additions and Diels-Alder cycloadditions under mild conditions.

Application

5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione serves as a versatile synthon in heterocyclic synthesis, enabling efficient access to substituted γ-lactones and pyran derivatives. Its stabilized α,β-unsaturated diketone system facilitates nucleophilic addition and cycloaddition reactions under mild conditions. The molecule exhibits excellent bench stability and ease of purification, making it ideal for iterative synthetic sequences in medicinal chemistry and natural product synthesis.

Synthesis

Route1
- In-stock
  
  2033-24-1
- 149-73-5
- ~85%
- In-stock
  
  15568-85-1
References
- Jourdain; Pommelet Synthetic Communications, 1997 , vol. 27, # 3 p. 483 - 492
Route2
- In-stock
  
  2033-24-1
- 122-51-0
- ~54%
- In-stock
  
  15568-85-1
References
- Morgentin, Remy; Pasquet, Georges; Boutron, Pascal; Jung, Frederic; Lamorlette, Maryannick; Maudet, Mickael; Ple, Patrick Tetrahedron, 2008 , vol. 64, # 12 p. 2772 - 2782

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302
Precautionary Statements : P264-P270-P330

Quality Control

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Computational Chemistry Data

TPSA 61.83
LogP 0.3528
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 1

Key Words

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5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

CAS No. 15568-85-1

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