1,4-Cyclohexanedione

1,4-Cyclohexanedione[1]
Chemical structure of Cyclohexanedione
Chemical structure of Cyclohexanedione
Names
Preferred IUPAC name
Cyclohexane-1,4-dione
Identifiers
3D model (JSmol)
774152
ChEBI
ChemSpider
ECHA InfoCard 100.010.279 Edit this at Wikidata
EC Number
  • 211-306-0
101292
KEGG
UNII
  • InChI=1S/C6H8O2/c7-5-1-2-6(8)4-3-5/h1-4H2 checkY
    Key: DCZFGQYXRKMVFG-UHFFFAOYSA-N checkY
  • InChI=1/C6H8O2/c7-5-1-2-6(8)4-3-5/h1-4H2
    Key: DCZFGQYXRKMVFG-UHFFFAOYAA
  • C1CC(=O)CCC1=O
Properties
C6H8O2
Molar mass 112.128 g·mol−1
Appearance White solid
Melting point 77 to 78.5 °C (170.6 to 173.3 °F; 350.1 to 351.6 K)
Boiling point 130 to 133 °C (266 to 271 °F; 403 to 406 K) (20 mmHg)
Very
Solubility Soluble in ethanol. Insoluble in diethyl ether.
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 132 °C (270 °F; 405 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

1,4-Cyclohexanedione is an organic compound with the formula (CH2)4(CO)2. This white solid is one of the three isomeric cyclohexanediones. This particular diketone is used as a building block in the synthesis of more complex molecules.

Preparation

1,4-Cyclohexanedione is prepared in two steps from diesters of succinic acid. Specifically under basic conditions, the diethyl succinate condenses to give the cyclohexenediol derivative diethylsuccinoylsuccinate. This intermediate can be hydrolysed and decarboxylated to afford the desired dione.[2]

This dione condenses with malononitrile to give an intermediate that can be dehydrogenated to tetracyanoquinodimethane (TCNQ).[3]

Reactions & Uses

Protection of one of the carbonyl groups with ethylene glycol affords 1,4-cyclohexanedione monoethylene glycol ketal aka 1,4-Dioxaspiro[4.5]decan-8-one [4746-97-8].[4][5] This compound is useful because it finds application in the synthesis of Ramatroban, Ciclindole, Flucindole, LY-344864 [1217756-94-9], Frovatriptan, Epibatidine,[6][7] Quinelorane,[8] Bromadol,[9][10] & C-8813.

References

  1. ^ MSDS for 1,4-Cyclohexanedione
  2. ^ Nielsen, Arnold T.; Carpenter, Wayne R. (1965). "1,4-Cyclohexanedione". Organic Syntheses. 45: 25. doi:10.15227/orgsyn.045.0025.
  3. ^ Strittmatter, Harald; Hildbrand, Stefan; Pollak, Peter (2007). "Malonic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_063.pub2. ISBN 978-3-527-30673-2.
  4. ^ 孙玉亮, et al. CN109503545 (2019 to Hebei caike New Material Technology Co.,Ltd.).
  5. ^ 王淑梅, et al. CN111039917 (2020 to Tsaker Chemical Zhangzhou Co ltd).
  6. ^ Hassner, A.; Belostotskii, A. M. (March 1995). "A simple method of preparation of 7-alkyl-7-azabicyclo[2.2.1]heptanes". Tetrahedron Letters. 36 (10): 1709–1712. doi:10.1016/0040-4039(95)00051-D.
  7. ^ Davis, C. R.; Johnson, R. A.; Cialdella, J. I.; Liggett, W. F.; Mizsak, S. A.; Marshall, V. P. (1 April 1997). "Microbiological Oxygenation of Bridgehead Azabicycloalkanes". The Journal of Organic Chemistry. 62 (7): 2244–2251. doi:10.1021/jo962192f.
  8. ^ Doll, M. K.-H.; Nichols, D. E.; Kilts, J. D.; Prioleau, C.; Lawler, C. P.; Lewis, M. M.; Mailman, R. B. (1 March 1999). "Synthesis and Dopaminergic Properties of Benzo-Fused Analogues of Quinpirole and Quinelorane". Journal of Medicinal Chemistry. 42 (5): 935–940. doi:10.1021/jm9804533.
  9. ^ Bernd Sundermann, Hagen-Heinrich Hennies, Werner Englberger, Stephan Wnendt, U.S. patent 7,183,436 (2007 to Gruenenthal Gmbh).
  10. ^ Bernd Sundermann, Hagen-Heinrich Hennies, Werner Englberger, Babette-Yvonne Koegel, U.S. patent 7,211,694 (2007 to Gruenenthal Gmbh).
allikas: https://en.wikipedia.org/wiki/1,4-cyclohexanedione