4729-21-9

Basic information

• Product Name: spiro[5.5]undeca-1,4-dien-3-one
• Synonyms: Spiro[5.5]undeca-1,4-dien-3-one
• CAS NO: 4729-21-9
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.2283
• Mol File: 4729-21-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 283.1°C at 760 mmHg
• Flash Point: 118.4°C
• Density: 1.03g/cm³
• Vapor Pressure: 0.00323mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: spiro[5.5]undeca-1,4-dien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: spiro[5.5]undeca-1,4-dien-3-one(4729-21-9)
• EPA Substance Registry System: spiro[5.5]undeca-1,4-dien-3-one(4729-21-9)

Safety Data

• Hazardous Substances Data: 4729-21-9(Hazardous Substances Data)

Usage

General Description

Spiro[5.5]undeca-1,4-dien-3-one, also known as SUDD or 1,4-Dien-3-one, is a chemical compound containing a spirocyclic ring system and a conjugated diene moiety. It is a bicyclic organic compound with a unique structure and is commonly used in the field of organic synthesis and medicinal chemistry. SUDD has been studied for its potential biological activities and has been identified as a key intermediate in the synthesis of various natural products and pharmaceuticals. Its distinct chemical properties make it a valuable building block for the development of novel compounds and materials.

Upstream product

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

Downstream Products

• 1215002-24-6 C₁₇H₁₈S 

Relevant articles and documents

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.

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.