What molecule am I?
Pagodane is a strained, highly symmetrical hydrocarbon. It is so named because its structure resembles that of anAsian pagoda. Its full name is [1.1.1.1]pagodane, and it belongs to the D2h point symmetry group.
Horst Prinzbach and colleagues at the University of Freiburg (Germany) and Ciba-Geigy (Basel, Switzerland) reported the synthesis of pagodane in 1987. According to the authors, “The synthesis of [pagodane] commences from isodrin1 and consists of ≈45 functional and structural modifications which are efficiently concentrated into 14 one-pot operations with an overall yieldof 24%.” The yield is amazingly high for such a complex synthesis.
Pagodane’s empirical formula, C20H20, is isomeric with that of dodecahedrane, the Molecule of the Week for February 22, 2021. Prinzbach and his coauthors anticipated that pagodane and its derivatives could be isomerized to the dodecahedrane structure.2 Yields were low at first, but they achieved suitable conversions from pagodane precursors by 1997.
Pagodane is not an article of commerce, so no hazard information is available for it. Similar compounds are considered to be nonhazardous except for possible low-level aquatic toxicity.
1. Isodrin is a hexachlorinated hydrocarbon and a now-banned insecticide.
2. Leo Paquette and co-workers at Ohio State University (Columbus) prepared dodecahedrane via a 29-step synthesis in 1982.
MOTW update
MDMA (3,4-methylenedioxymethamphetamine) was the Molecule of the Week for August 19, 2019. It is a widely abused psychoactive drug known on the street as “ecstasy”. MDMA, however, may have a beneficial use. Jennifer M. Mitchell at the University of California, San Francisco and colleagues there and at several other institutions worldwide report that the drug is efficacious in patients with severe post-traumatic stress disorder (PTSD).Their randomized, double-blind, placebo-controlled phase 3 study was conducted with 90 participants at 15 sites in three countries.
This molecule was suggested by a reader. We present almost all of the molecules suggested by our readers. If you have a molecule you would like us to consider, please send us a message. And thank you for your interest in Molecule of the Week! —Ed.
Pagodane fast facts
| CAS Reg. No. | 89683-62-5 |
| SciFinder nomenclature | 2,7,8b,3,4b,6-Ethane-diylidyne-dipentalenol-[1,6-ab:1′,6′-ef]-pentalene, hexadecahydro- |
| Empirical formula | C20H20 |
| Molar mass | 260.37 g/mol |
| Appearance | White crystalline solid |
| Melting point | 243 ºC |
| Water solubility | Insoluble |
Learn more about this molecule from CAS, the most authoritative and comprehensive source for chemical information.
Molecule of the Week needs your suggestions!
If your favorite molecule is not in our archive, please send us a message. The molecule can be notable for its current or historical importance or for any quirky reason. Thank you!
Stay Ahead of the Chemistry Curve
Learn how ACS can help you stay ahead in the world of chemistry.
