13705-37-8

Usage

InChI:InChI=1/C12H16O/c1-10(13)12(2,3)9-11-7-5-4-6-8-11/h4-8H,9H2,1-3H3

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 917-64-6 methyl magnesium iodide 
• 35863-45-7 2,2-dimethyl-3-phenylpropanenitrile 
• 917-54-4 methyllithium 
• 1901-26-4 3-methyl-4-phenyl-3-buten-2-one 
• 74-88-4 methyl iodide 

Downstream Products

• 760999-19-7 2,5-bis(1,1-dimethyl-2-phenylethyl)-2,4-dihydroxyfuran-3(2H)-one 
• 760999-16-4 2,2,7,7-tetramethyl-1,8-diphenyloctane-3,4,5,6-tetraone 
• 642040-27-5 1,1,1-trifluoro-4,4,-dimethyl-5-phenyl-3-pentanone 
• 760999-17-5 3,3-dimethyl-2-oxo-4-phenylbutyraldehyde 
• 13395-01-2 2,3,3-Trimethyl-4-phenyl-1-butene 

Relevant academic research and scientific papers

Novel selective anti-androgens with a diphenylpentane skeleton

We have proposed a multi-template approach for drug development, focusing on similar fold structures of proteins, and have effectively generated lead compounds for several drug targets. Modification of these polypharmacological lead compounds is then needed to generate target-selective compounds. In the work presented here, we aimed at separation of the anti-androgen activity and vitamin D activity of previously identified diphenylpentane lead compounds. Based on the determined X-ray crystal structures of androgen receptor and vitamin D receptor, bulky substituents were introduced at the t-butyl group in the lead compounds 2 and 3. As a result of this structural development, we obtained 16c, which exhibits more potent anti-androgen activity (IC 50: 0.13 μM) than clinically used anti-androgen bicalutamide (IC50: 0.67 μM) with 30-fold selectivity over vitamin D activity. This result indicates that lead compounds obtained via the multi-template approach can indeed be structurally modified to generate target-selective compounds.

A cyclic vicinal bis(tetraketone) and structural investigations of formoins

Investigations of simple formoins such as 2,5-bis(1,1-dimethyl-2- phenylethyl)-2,4-dihydroxyfuran-3(2H)-one (17), benzoylformoin (18), p-toluoylformoin (19), pivaloylformoin (20), and the 2,4-dihydroxy-2,5- bis(heterocycl-2-yl)furan-3-ones 21-23 (heterocycle = furan, thiophene, selenophene) by NMR spectroscopy in DMSO showed the dihydroxyfuranone skeleton and not an enediol structure. The formoin 17 was oxidized to the corresponding tetraketone 10, The intermolecular double benzoin condensation of 1,4-bis(2,2-dimethyl-3,4-dioxobutyl)benzene (27) affords, in low yield, the bis(formoin) 29, and this could be oxidized to provide 2,2,2′,2′,7, 7,7′,7′-octamethyl[8.8]paracyclophan-3,3′,4,4′5, 5′6,6′-octaone (9). The molecular structures of 17 and 29, the monohydrate of 10 (30), and also the dihydrate of 9 (31) are reported. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Reductive cleavage of 2-methyleneoxetanes with lithium and 4,4'-di-tert- butylbiphenyl

3,3-Dimethyl-2-mcthylene-4-phenyloxetane (5) undergoes reductive cleavage with lithium and 4,4'-di-tertbutylbiphenyl (DTBB) to give an intermediate dianion, which reacts regioselectively with aldehydes and ketones to give aldol adducts in modest yields. A

Rearrangement of 1,3-Diradicals. Arylcyclopropane Photochemistry

The photochemistry of a series of aryl-substituted cyclopropanes was investigated as part of our continuing investigations of these systems.The literature held a puzzling discrepancy in which several similar reactants exhibited differing photochemistry.A series of 3-aryl-1,1,2,2-tetramethylcyclopropanes was found to rearrange photochemically to give primarily two types of products, the anticipated 4-aryl-2,3,3-trimethyl-1-butenes and, additionally, 1-aryl-2,3,3-trimethyl-1-butenes.The latter arise from regioselective methyl migration of intermediate singlet 1,3-diradicals.Also, the usual Griffin carbene fragmentation was encountered as a minor pathway.Biphenylyl-, p-cyanophenyl-, and p-anisyl-substituted cyclopropanes were studied.Also, the photochemistry of 3-phenyl-1,1,2,2-tetramethylcyclopropane was reinvestigated and found to conform to the general pattern of reactivity.Throughout, it was the singlet excited states responsible for the observed reactivity, and the triplet counterparts were found to be unreactive.In addition, the photochemistry of 3-biphenylyl-2,2-dimethyl-1,1-diphenylcyclopropane was studied.Again, the triplet was unreactive.The singlet gave rise to 4-biphenylyl-2-methyl-3,3-diphenyl-1-butene exclusively.The differing behavior of the various arylcyclopropanes is discussed from a mechanistic viewpoint.In the case of the 3-aryl-1,1,2,2-tetramethylcyclopropanes, the regioselectivity of the 1,3-diradical intermediate favors migration toward the less delocalized odd-electron center.This selectivity is understood on a quantum mechanical basis.Finally, quantum yields are reported.

Preparation of methyl ketones

A process for the preparation of a methyl ketone of the formula STR1 in which R1 is alkyl, alkenyl, alkinyl, optionally substituted aryl or optionally substituted heteroaryl, R2 is alkyl, R3 is alkyl or R2 and R3, together with the carbon atom to which they are bonded, from a cycloalkyl ring, comprising reacting a methyl sec.-alkyl ketone of the formula STR2 with a halide of the formula in which X is halogen, in the presence of a base, a diluent, and a phase-transfer catalyst.

Prostaglandin derivatives

Derivatives of 11-deoxy-PGE2 are prepared. These new compounds not heretofore found in nature possess various pharmacological activities, one of which is bronchodilation.