Penguinone

Penguinone
Names
	Preferred IUPAC name 3,4,4,5-Tetramethylcyclohexa-2,5-dien-1-one
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 a 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 978-1848162075.
^ 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. Archived from the original on 2016-10-18. Retrieved 2014-12-01.
^ "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 (12): 3884––3894. doi:10.1002/cber.19831161212.

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