Derivatives of dihydronepetalactone and method for preparation

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C514S456000

Reexamination Certificate

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07067678

ABSTRACT:
3-substituted dihydronepetalactone is prepared by deprotonation of nepetalactone and treatment with Grignard reagent to form alkyl and aryl substituted compounds. The compounds so prepared are odorous and have a wide range of utility ranging from insect repellents to fragrance compounds, such as perfumes, among others.

REFERENCES:
patent: WO 03/084946 (2003-10-01), None
Eisenbraun, et al., “Structure of Nepetalic Acid in the Solid State an in Solution by X-ray Diffraction and Nuclear Magnetic Resonance Analysis”, J. Org. Chem. (1981), pp. 3302-3305, vol. 46, Oklahoma.
McElvain, et al., “The Constituents of the Volatile Oil of Catnip. I. Nepetalic Acid, Nepetalactone and Related Compounds”, J. Chem. Soc., (1941), pp. 1558-1563, vol. 63, Wisconsin.
Dawson, et al., “The Aphid Sex Pherome Cyclopentanoids: Synthesis in the Elucidation of Structure and Biosysnthetic Pathways”, Bioorganic & Medicinal Chemistry (1996), pp. 351-361, vol. 4, No. 3, Great Britain.
Eisenbraun, et al., “(4aS, 7S, 7aR)”, et al., J. Org. Chem. (1988), pp. 3968-3972, vol. 53, California.
Hiromichi Ohta et. al., Regiospecific Introduction of Two Carbon Moieties into the Vicinal Positions of Cyclopentadiene and Synthesis of C9-Terpene Lactones, J. Org. Chem., 1977, pp. 1231-1235, vol. 42.
International Search Report Dated Jun. 3, 2005, International Application No. PCT/US2004/039511, Filing Date: Nov. 24, 2004.

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