Grundmann's Ketone
Structural Formula Vector Image
Title: Grundmann's Ketone
CAS Registry Number: 66251-18-1
CAS Name: (1R,3aR,7aR)-1-[(1R)-1,5-Dimethylhexyl]octahydro-7a-methyl-4H-inden-4-one
Additional Names: (1R,3aR,7aR)-7a-methyl-1-((R)-6-methylheptan-2-yl)-octahydroinden-4-one; Windaus-Grundmann ketone
Molecular Formula: C18H32O
Molecular Weight: 264.45
Percent Composition: C 81.75%, H 12.20%, O 6.05%
Literature References: Prepd by ozonolysis of vitamin D3, q.v. Preparative method: A. Windaus, W. Grundmann, Ann. 524, 295 (1936). Prepn: H. H. Inhoffen et al., Ber. 90, 664 (1957). Synthetic applications: H. Nemoto et al., J. Org. Chem. 51, 5311 (1986); P. Bovicelli et al., ibid. 57, 5052 (1992); M. C. Clasby, D. Craig, Synth. Commun. 24, 481 (1994); R. R. Sicinski, H. F. DeLuca, Bioorg. Med. Chem. Lett. 5, 159 (1995); W. H. Okamura et al., J. Org. Chem. 67, 1637 (2002).
Properties: Colorless oil, bp0.001 115-120°. [a]D20 +8.9°.
Boiling point: bp0.001 115-120°
Optical Rotation: [a]D20 +8.9°
Use: Intermediate in the synthesis of vitamin D active compounds.

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