36412-64-3

Basic information

• Product Name: 2-BROMO-1-(4-METHOXY-PHENYL)-PENTAN-1-ONE
• Synonyms: 2-BROMO-1-(4-METHOXY-PHENYL)-PENTAN-1-ONE
• CAS NO: 36412-64-3
• Molecular Formula: C₁₂H₁₅BrO₂
• Molecular Weight: 271.1503
• Mol File: 36412-64-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-BROMO-1-(4-METHOXY-PHENYL)-PENTAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-1-(4-METHOXY-PHENYL)-PENTAN-1-ONE(36412-64-3)
• EPA Substance Registry System: 2-BROMO-1-(4-METHOXY-PHENYL)-PENTAN-1-ONE(36412-64-3)

Safety Data

• Hazardous Substances Data: 36412-64-3(Hazardous Substances Data)

Upstream product

• 1671-76-7 p-Methoxyvalerophenon 
• 2589-71-1 4'-hydroxyvalerophenone 
• 638-29-9 n-valeryl chloride 
• 100-66-3 methoxybenzene 

Downstream Products

• 381229-24-9 1,3-bis-(4-methoxy-phenyl)-4-phenyl-2-propyl-butane-1,4-dione 
• 381229-21-6 1,3,4-tris-(4-methoxy-phenyl)-2-propyl-butane-1,4-dione 
• 386748-00-1 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1,4-bis-(4-methoxy-phenyl)-3-propyl-butane-1,4-dione 
• 14979-97-6 4'-methoxy-α-pyrrolidinopentiophenone 
• 13415-87-7 2-pyrrolidin-1-yl-1-(4'-hydroxy-phenyl)-pentan-1-one 
• 612824-88-1 2,5-bis-n-propyl-3,6-bis-(4'-methoxyphenyl)-pyrazine 
• 381229-36-3 2,4-bis-(4-methoxy-phenyl)-5-phenyl-3-propyl-furan 
• 381229-33-0 2,3,5-tris(4-methoxyphenyl)-4-propylfuran 
• 386748-07-8 4-[2,5-bis-(4-methoxy-phenyl)-4-propyl-furan-3-yl]-phenol 
• 386748-13-6 1-(2-{4-[2,5-bis-(4-methoxy-phenyl)-4-propyl-furan-3-yl]-phenoxy}-ethyl)-piperidine 

Relevant articles and documents

Kinetic diastereomer differentiation in Au(III)- and Bi(III)-catalyzed benzylic arylation: Concise and stereocontrolled synthesis of 2-amino-1,1-diarylalkanes

Benzylic alcohols carrying an adjacent α-nitro or α-azido group on the alkane chain are converted into syn-1,1-diaryl-2-nitro- and 2-azidoalkanes with electron-rich arenes in stereoselective reactions catalyzed by Bronsted and Lewis acids. Gold(III) chloride and bismuth(III) triflate were found to be especially efficient as catalysts, showing kinetically controlled differentiation in the reactivity of diastereomeric α-substituted benzyl alcohols. Applications to therapeutically relevant syn- and anti- 2-amino-1,1-diarylalkanes are projected.

1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors

Dopamine, serotonin, and norepinephrine are essential for neurotransmission in the mammalian system. These three neurotransmitters have been the focus of considerable research because the modulation of their production and their interaction at monoamine receptors has profound effects upon a multitude of pharmacological outcomes. Our interest has focused on neurotransmitter reuptake mechanisms in a search for medications for cocaine abuse. Herein we describe the synthesis and biological evaluation of an array of 2-aminopentanophenones. This array has yielded selective inhibitors of the dopamine and norepinephrine transporters with little effect upon serotonin trafficking. A subset of compounds had no significant affinity at 5HT1A, 5HT1B, 5HT1C, D1, D2, or D3 receptors. The lead compound, racemic 1-(4-methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one 4a, was resolved into its enantiomers and the S isomer was found to be the most biologically active enantiomer. Among the most potent of these DAT/NET selective compounds are the 1-(3,4-dichlorophenyl)- (4u) and the 1-naphthyl- (4t) 2-pyrrolidin-1-yl-pentan-1-one analogues.

Estrogenic diazenes: Heterocyclic non-steroidal estrogens of unusual structure with selectivity for estrogen receptor subtypes

Estrogens regulate many biological functions, often acting in a tissue-selective manner. Their tissue-selective action is believed to involve differential estrogen action through the two estrogen receptor (ER) subtypes, ERα and ERβ, as well as differential interaction of the ligand-receptor complexes with promoters and coregulator proteins. In the latter case, selectivity is based on the induction of specific conformations of the ligand-ER complex, conformations that are influenced by the structure of the ligand. Estrogen pharmaceuticals having an ideal balance of tissue-selective activity are being sought for menopausal hormone replacement, breast cancer prevention and therapy, and other actions. To expand on the structural diversity of ER ligands that might show such tissue selectivity, we have prepared a series of diazenes (pyrazines, pyrimidines, and pyridazines) substituted with two to four aryl groups and various short-chain aliphatic substituents. All of the pyrazine and pyrimidines bind to ER, some with high affinity and with a considerable degree of preferential binding to either ERα or ERβ. One pyrimidine and one pyrazine have ERα affinity preferences as high as 23 and 9, respectively, and one pyrimidine has an ERβ affinity preference of 8. The pyridazines, by contrast, are quite polar and have only very low binding affinity for the ER. In cell-based transcription assays, several of the pyrimidines and a pyrazine were found to be considerably more agonistic on ERα than on ERβ. Because these triaryl diazenes have the largest volumes among the ER ligands so far investigated, their high affinity demonstrates the flexibility of the ligand binding pocket of the ERs and its tolerance for large substituents. Thus, these novel heterocyclic ligands expand the repertoire of chemical structures that bind to the estrogen receptor, and they could prove to be useful in elucidating the biological behavior of the two ER subtypes and in forming the basis for new estrogen pharmaceuticals having desirable tissue selectivity.