4729-21-9

Usage

Uses

Used in Organic Synthesis:
Spiro[5.5]undeca-1,4-dien-3-one is used as a key intermediate in organic synthesis for its distinctive chemical properties, enabling the development of novel compounds and materials.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Spiro[5.5]undeca-1,4-dien-3-one is utilized as a precursor in the synthesis of various pharmaceuticals, contributing to the creation of new drugs and therapeutic agents.
Used in Natural Product Synthesis:
Spiro[5.5]undeca-1,4-dien-3-one is employed as a crucial component in the synthesis of natural products, facilitating the production of complex organic molecules with potential biological activities.
Used in Pharmaceutical Development:
As a valuable building block, Spiro[5.5]undeca-1,4-dien-3-one is used in the development of pharmaceuticals, playing a significant role in the advancement of new treatments and medications.

Upstream product

• 108-75-8 2,4,6-trimethyl-pyridine 
• 879406-91-4 cis-2,4-dibromo-spiro[5.5]undecan-3-one 
• 75-65-0 tert-butyl alcohol 
• 30834-42-5 spiro[5.5]undec-1-en-3-one 
• 103502-23-4 5-bromo-1-(4-hydroxyphenyl)pentane 

Downstream Products

• 1215002-24-6 C₁₇H₁₈S 

Relevant academic research and scientific papers

NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer. Part I. Discovering the guidelines

The development of "molecular rulers" would allow one to quantitatively locate intercalants within the liposomal bilayer. To this end, we have attempted to correlate the 13C NMR chemical shift of a polarizable "reporter" carbon (e.g., carbonyl) of the intercalant-with the ET(30) polarity it experiences, and with its Angstrom distance from the interface. This requires families of molecules with the same two "reporter carbons" separated by a fixed distance, residing at various depths/polarities within the bilayer. The families studied included 4,4-dialkylcyclohexa-2,5-dienones 1, benzenediacetic esters 15, benzenedipropionic esters 17, 4-alkoxybenzaldehydes 19 and methyl 4-alkoxybenzoates 22. These compounds possessed the following characteristics: (1) a planar backbone; (2) polar/hydrophilic "head" groups; (3) modular hydrophobic tails; (4) large changes in the 13C NMR chemical shift (Δδ) of the reporter atoms with solvent polarity. These studies revealed a fifth requirement, namely: (5) the reporter carbons must not be strongly conjugated, lest it reflect the charge build-up at another site within the conjugated system.

A Practical Catalytic Method for the Preparation of Steroidal 1,4-Dien-3-ones by Oxygen Atom Transfer from Iodoxybenzene to Diphenyl Diselenide

The dehydrogenation of steroidal 3-ketones can be accomplished in high yield using benzeneseleninic anhydride generated in situ by efficient oxygen atom transfer from iodoxybenzene to catalytic amounts of diphenyl diselenide.An experimentally convenient and economical development of this catalytic cycle is the use of meta-iodoxybenzoic acid which both avoids chromatography and allows recovery of meta-iodobenzoic acid and diphenyl diselenide. 12-Hydroxy- and 12-keto-steroids are also dehydrogenerated very efficiently using this catalytic process.

Oxygen Atom Transfer from Iodylbenzene to Diphenyl Diselenide - A Convenient Method for Dehydrogenation of Steroidal 3-Ketones

Steroidal 3-ketones are smoothly dehydrogenated in high yield using benzeneseleninic anhydride generated in situ by oxygen atom transfer from iodylbenzene, PhIO2, to catalytic amounts of diphenyl diselenide; use of meta-iodylbenzoic acid in the above cycle has led to the development of an economical and experimentally convenient method avoiding chromatographic separations and with recovery of the m-iodobenzoic acid and the diphenyl diselenide.

Anti-androgen compounds

Compounds of the formula STR1 in which each R is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, cyano, or halo, and both R groups are identical and are symmetrically located; R 1 is C 1 -C 3 alkyl and R 2 is methyl, or R 1 and R 2 taken together are (CH 2 -- n in which n is an integer from 4 to 6; and (1) X c and X d are hydrogen, and the combination of X a and Y a and of X b and Y b each represents a double bond, subject to the limitation that, when R 1 is C 1 -C 3 alkyl and is other than methyl, X c, X d, and R 1 are all in an α-configuration; or (2) X a, X b, X c, X d, Y a, and Y b are hydrogen, subject to the limitation that both X c and X d are in an α-configuration, both X a and X b are in an α-configuration or in a β-configuration, and, R 1, when it is C 1 -C 3 alkyl, is in an α-configuration, are useful in inhibiting the action of androgens or are intermediates to such anti-androgen compounds.