Penguinone

Penguinone
Skeletal formula of penguinone	Space-filling model of the penguinone molecule
Names
	IUPAC name 3,4,4,5-Tetramethylcyclohexa-2,5-dienone
Identifiers
CAS Number	34014-87-4;
3D model (JSmol)	Interactive image;
ChemSpider	10338857;
PubChem CID	12564106;
CompTox Dashboard (EPA)	DTXSID70502708 ;
	InChI InChI=1S/C10H14O/c1-7-5-9(11)6-8(2)10(7,3)4/h5-6H,1-4H3 Key: RHIYIMQPIGYWEK-UHFFFAOYSA-N; InChI=1/C10H14O/c1-7-5-9(11)6-8(2)10(7,3)4/h5-6H,1-4H3 Key: RHIYIMQPIGYWEK-UHFFFAOYAI;
	SMILES CC1=CC(=O)C=C(C1(C)C)C;
Properties
Chemical formula	C10H14O
Molar mass	150.221 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Penguinone is an organic compound with the molecular formula C
₁₀H
₁₄O. Its name comes from the fact that its 2-dimensional molecular structure resembles a penguin.[1][2]

The suffix "-one" indicates that it is a ketone.[3] The systematic name of the molecule is 3,4,4,5-tetramethylcyclohexa-2,5-dienone.[4][5]

Although it is a dienone and thus has the necessary structure for Dienone-Phenol Rearrangement, the methyl groups in positions 3 and 5 of the ring block the movement of the group at position 4, so even the action of trifluoroacetic acid will not cause transformation to a phenol.[6]

References

May, Paul (2008). Molecules with Silly or Unusual Names. Imperial College London. p. 35. ISBN 1848162073.
May, Paul (23 October 2014). "Molecules with Silly or Unusual names". University of Bristol. Retrieved 1 December 2014.
Laszlo, Pierre (2004). "Science as Play". American Scientist. 92 (5): 398. doi:10.1511/2004.5.398.
"Chemical structures beginning with P". about.com. Archived from the original on 21 December 2009. Retrieved 1 December 2014.
Parkvall, Mikael (2006). Limits of Language. London: Battlebridge. p. 176. ISBN 1903292042.
Hagenbruch, Bernd; Hünig, Siegfried (1983). "Ein Beitrag zur Dienon-Phenol-Umlagerung". Chemische Berichte (in German). 116: 3884––3894. doi:10.1002/cber.19831161212.

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[1] May, Paul (2008). Molecules with Silly or Unusual Names. Imperial College London. p. 35. ISBN 1848162073.

[2] May, Paul (23 October 2014). "Molecules with Silly or Unusual names". University of Bristol. Retrieved 1 December 2014.

[3] Laszlo, Pierre (2004). "Science as Play". American Scientist. 92 (5): 398. doi:10.1511/2004.5.398.

[4] "Chemical structures beginning with P". about.com. Archived from the original on 21 December 2009. Retrieved 1 December 2014.

[5] Parkvall, Mikael (2006). Limits of Language. London: Battlebridge. p. 176. ISBN 1903292042.

[6] Hagenbruch, Bernd; Hünig, Siegfried (1983). "Ein Beitrag zur Dienon-Phenol-Umlagerung". Chemische Berichte (in German). 116: 3884––3894. doi:10.1002/cber.19831161212.

Penguinone

See also

References