Hagemann's ester

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Hagemann's ester
Names
Preferred IUPAC name
Ethyl 2-methyl-4-oxocyclohex-2-ene-1-carboxylate
Other names
Ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate
4-Carbethoxy-3-methyl-2-cyclohexen-1-one
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.006.962 Edit this at Wikidata
EC Number
  • 207-657-4
UNII
  • InChI=1S/C10H14O3/c1-3-13-10(12)9-5-4-8(11)6-7(9)2/h6,9H,3-5H2,1-2H3 ☒N
    Key: VLTANIMRIRCCOQ-UHFFFAOYSA-N ☒N
  • InChI=1/C10H14O3/c1-3-13-10(12)9-5-4-8(11)6-7(9)2/h6,9H,3-5H2,1-2H3
    Key: VLTANIMRIRCCOQ-UHFFFAOYAX
  • O=C(OCC)C1C(=C\C(=O)CC1)/C
Properties[1]
C10H14O3
Molar mass 182.219 g·mol−1
Density 1.078 g/mL
Boiling point 268 to 272 °C (514 to 522 °F; 541 to 545 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Hagemann's ester, ethyl 2-methyl-4-oxo-2-cyclohexenecarboxylate, is an

sterols, trisporic acids, and terpenoids
.

Preparation

Hagemann's approach

cyclization. Finally, heat is applied to generate Hagemann's ester.[2][3]

Knoevenagel's approach

Soon after Hagemann, Emil Knoevenagel described a modified procedure to produce the same intermediate diethyl ester of 2,4-diacetyl pentane using

catalytic amount of piperidine.[3]

Newman and Lloyd approach

2-Methoxy-1,3-butadiene and ethyl-2-butynoate undergo a

hydrolyzed to obtain Hagemann's ester. By varying the substituents on the butynoate starting material, this approach allows for different C2 alkylated Hagemann's ester derivatives to be synthesized.[3]

Mannich and Forneau approach

Original

Methyl vinyl ketone, ethyl acetoacetate, and diethyl-methyl-(3-oxo-butyl)-ammonium iodide react to form a cyclic aldol product. Sodium methoxide is added to generate Hagemann's ester.

Variations

Methyl vinyl ketone and ethyl acetoacetate undergo aldol cyclization in the presence of catalytic

Triton B or sodium ethoxide to produce Hagemann's ester.[3] This variant is a type of Robinson annulation.[4]

Uses

Hagemann's ester has been used as a key building block in many

dimers[7] or in reactions forming simple derivatives.[8][9][10]

References

  1. ^ 2-methyl-4-oxo-2-cyclohexenecarboxylate at Sigma-Aldrich
  2. doi:10.1002/cber.189302601181
    .
  3. ^
    doi:10.1016/j.tet.2010.01.078
    .
  4. doi:10.1039/JR9350001285
    .
  5. doi:10.1021/jo00930a001
    .
  6. PMID 18918810
    .
  7. doi:10.1055/s-0034-1379001
    .
  8. doi:10.1039/P19790001837
    .
  9. doi:10.1039/P19720001836
    .
  10. doi:10.1039/P19720000602
    .
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