10228. Dianin's Compound

Nomenclature

CAS number: 472-41-3
4-(3,4-Dihydro-2,2,4-trimethyl-2H-1-benzopyran-4-yl)phenol; 4-p-hydroxyphenyl-2,2,4-trimethylchroman; p-(2,2,4-trimethyl-4-chromanyl)phenol.
C18H20O2; mol wt 268.35.
C 80.56%, H 7.51%, O 11.92%.

Description and references

Organic clathrate; six host molecules form an hourglass-shaped cage to create inclusion complexes with small molecule guest compounds. Prepn from phenol and mesityl oxide: A. P. Dianin, J. Russ. Phys. Chem. Soc. 36, 1310 (1914); and characterization of inclusion compounds: W. Baker et al., J. Chem. Soc. 1956, 2010 DOI; K. J. Harrington, C. P. Garland, Sep. Sci. Technol. 17, 1339 (1982) DOI; idem, ibid. 17, 1443 (1982-83) DOI. Crystal structure of clathrates with ethanol and chloroform, and cage characterization: J. L. Flippen et al., J. Am. Chem. Soc. 92, 3749 (1970) DOI. Crystal structure of "guest-free" cage: F. Imashiro et al., Acta Crystallogr. C54, 1357 (1998) DOI.

Chemical structure

Properties

Ethanol solvate: hexagonal needles from ethanol, mp 165-166°. Unsolvated form: fine needles, mp 156-157°. d 1.160. Sol in hot aq NaOH or KOH. Log P (octanol/water): 4.487.

Use

Model compound in host-guest chemistry studies.