138509-45-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-2-(cyclopentyloxy)-1-methoxybenzene is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of biologically active compounds. Its unique structure allows for the creation of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical field, 4-Bromo-2-(cyclopentyloxy)-1-methoxybenzene serves as a crucial component in the production of agrochemicals, aiding in the development of effective pesticides, herbicides, and other crop protection agents. Its incorporation into these products can enhance their efficacy and selectivity.
Used in Organic Synthesis:
4-Bromo-2-(cyclopentyloxy)-1-methoxybenzene is utilized as a reagent in organic synthesis, where its distinct functional groups facilitate a variety of chemical reactions. This makes it an essential component in the creation of complex organic molecules for research and commercial applications.
Used in Research and Development:
4-Bromo-2-(cyclopentyloxy)-1-methoxybenzene is also used in research and development settings as a probe to study the effects of structural modifications on the properties and reactivity of benzene derivatives. Its unique structure provides opportunities for exploring new reaction pathways and mechanisms in organic chemistry.

Upstream product

• 96-41-3 Cyclopentanol 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 31083-15-5 2-Methoxyphenyltrifluoracetat 
• 1972-28-7 diethylazodicarboxylate 
• 137-43-9 Cyclopentyl bromide 
• 60-29-7 diethyl ether 
• 108-95-2 phenol 
• 584-08-7 potassium carbonate 
• 1687-53-2 5-amino-2-methoxyphenol 
• 21702-84-1 2,4-dibromoanisole 
• 531-37-3 2-methoxyphenyl benzoate 
• 25016-01-7 5-bromo-2-methoxybenzaldehyde 
• 90-05-1 2-methoxy-phenol 
• 66037-04-5 1-acetoxy-5-bromo-2-methoxybenzene 

Downstream Products

• 159612-90-5 3'-Cyclopentyloxy-4'-methoxy-biphenyl-3-carboxylic acid methyl ester 
• 191610-54-5 (4R,5S)-1-tert-butoxycarbonyl-5-tert-butyldiphenylsiloxymethyl-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidine-2-one 
• 61413-54-5 Rolipram 
• 180320-55-2 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane 
• 159613-21-5 3-cyclopentyloxy-4-methoxyphenylboronic acid 
• 658081-58-4 2-(3-(cyclopentyloxy)-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 894421-52-4 (E)-ethyl 3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate 
• 894421-55-7 (Z)-ethyl 4-bromo-3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate 
• 894421-61-5 (Z)-ethyl 4-azido-3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate 
• 85416-75-7 (R)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one 
• 85416-73-5 (S)-rolipram 
• 440103-24-2 (3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2-pentalenone 
• 439919-24-1 (3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2(1H)-pentalenone 
• 439919-39-8 (3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydro-2-pentalenol 

Relevant academic research and scientific papers

Synthesis and assessment of catechol diether compounds as inhibitors of trypanosomal phosphodiesterase B1 (TbrPDEB1)

Human African trypanosomiasis (HAT) is a parasitic neglected tropical disease that affects 10,000 patients each year. Current treatments are sub-optimal, and the disease is fatal if not treated. Herein, we report our continuing efforts to repurpose the human phosphodiesterase 4 (hPDE4) inhibitor piclamilast to target trypanosomal phosphodiesterase TbrPDEB1. We prepared a range of substituted heterocyclic replacements for the 4-amino-3,5-dichloro- pyridine headgroup of piclamilast, and found that these compounds exhibited weak inhibitory activity of TbrPDEB1.

Enantioselective Flow Synthesis of Rolipram Enabled by a Telescoped Asymmetric Conjugate Addition-Oxidative Aldehyde Esterification Sequence Using in Situ-Generated Persulfuric Acid as Oxidant

A novel approach is reported for the enantioselective flow synthesis of rolipram comprising a telescoped asymmetric conjugate addition-oxidative aldehyde esterification sequence followed by trichlorosilane-mediated nitro group reduction and concomitant la

Synthesis of a TNF inhibitor, flurbiprofen and an: I -Pr analogue in enantioenriched forms by copper-catalyzed propargylic substitution with Grignard reagents

The copper-catalyzed substitution reaction of diethyl phosphate derived from TMSCCCH(OH)CH2CH2OTBDPS with 3-c-C5H9-4-MeOC6H3MgBr, followed by several transformations, afforded a tumor necrosis factor inhibitor possessing a Ph-acetylene moiety. The inhibitor was also synthesized from phenylacetylene phosphate PhCCCH(OP(O)(OEt)2)CH2CH2OTBDPS. Furthermore, the substitution of phosphates derived from TMSCCCH(OH)CH3 and TMSCCCH(OH)-i-Pr with 3-F-4-PhC6H3MgBr gave the corresponding substitution products, which were transformed to flurbiprofen and its i-Pr analogue, respectively. The copper-catalyzed substitutions in these syntheses proceeded in a regio- and stereoselective manner. This journal is

Synthesis of 1-[3-(Cyclopentyloxy)-4-methoxyphenyl]cyclopentanol as potential phosphodiesterase-4 inhibitor

The enzyme phosphodiesterase-4 (PDE4) plays a key role in many physiological or pathological processes in mammalian organs, where its inhibition increases cyclic adenosine monophosphate (cAMP) causing benefits in many diseases or conditions. The aim of this study is to synthesize 1-(3-(cyclopentyloxy)-4-methoxyphenyl)cyclopentanol (6) as potential phosphodiesterase-4 inhibitor. Starting from 2- methoxy phenol (1), 4-bromo-2-(cyclopentyloxy)-1-methoxybenzene (5) was synthesized in good yields. 1-[3-(Cyclopentyloxy)-4- methoxyphenyl]cyclopentanol (6) was prepared from 5 using two different methods.

Co-catalyzed reductive cyclization of azido and cyano substituted α,β-unsaturated esters with NaBH4: enantioselective synthesis of (R)-baclofen and (R)-rolipram

Sodium borohydride in combination with a catalytic amount of CoCl2 has been found to be an excellent catalytic system in reductive cyclizations of suitably substituted azido and cyano groups of α,β-unsaturated esters to afford γ and δ-lactams in high yields. The process has been demonstrated for the enantioselective synthesis of (R)-baclofen, (R)-rolipram, and (R)-4-fluorophenylpiperidinone, a key intermediate for (-)-paroxetine.

Process and intermediates for making 4-cyanosubstituted cyclohexanoic acids

Herein is provided a process for preparing substituted cyclohexanoic acids of formula (I), where Rais a carbon-containing group optionally linked by oxygen, sulfur or nitrogen to the phenyl ring and j is 1-5; and one of R and R* is hydrogen and the other is C(O)OH.

Novel selective PDE4 inhibitors. 2. Synthesis and structure-activity relationships of 4-aryl-substituted cis-tetra- and cis-hexahydrophthalazinones

A series of 4-aryl-substituted cis-4a,5,8,8a-tetra- and cis-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-ones with high inhibitory activity toward cAMP-specific phosphodiesterase (PDE4) was synthesized. To study structure-activity relationships various substituents were introduced to the 2-, 3-, and 4-positions of the 4-phenyl ring. Substitution at the 4-position of the phenyl ring was restricted to a methoxy group, probably due to unfavorable steric interactions of larger groups with the binding site. The introduction of many alkoxy substituents including distinct ring systems and functional groups was allowed to the 3-position. It was found that in general the cis-4a,5,8,8a-tetrahydro-2H-phthalazin-1-ones are more potent than their hexahydrophthalic counterparts, the best activity residing in (4-imidazol-1-yl-phenoxy)butoxy analogue 16o (pIC50 = 9.7).

Substituted β-thiocarboxylic acids

This invention relates to compounds of general formula (I): in which Ar is a group selected from: A1, A2, B, C, D, E, Q1-Q3, R1-R9, Z1and Z2are as defined in the disclosure, and Y represents carboxy or an acid bioisostere. These compounds inhibit the production or physiological effects of TNF and inhibit cyclic AMP phosphodiesterase. The invention is also directed to pharmaceutical compositions comprising compounds of formula (I), their pharmaceutical use and methods for their preparation.

Synthesis of SB 222618. A potential PDE IV inhibitor

PDE IV inhibitor SB 222618 was prepared by regioselective S(N)2' addition of 9 to bromoallene 6a followed by a stereoselective borane reduction of 4 to afford 2 which by a palladium mediated coupling with 3, delivered SB 222618 (1) in good yield. (C) 2000 Elsevier Science Ltd.

COMPOUNDS CONTAINING PHENYL LINKED TO ARYL OR HETEROARYL BY AN ALIPHATIC- OR HETEROATOM-CONTAINING LINKING GROUP

This invention is directed to the pharmaceutical use of phenyl compounds, which are linked to an aryl moiety by various linkages, for inhibiting tumor necrosis factor. The invention is also directed to the compounds, their preparation and pharmaceutical compositions containing these compounds. Furthermore, this invention is directed to the pharmaceutical use of the compounds for inhibiting cyclic AMP phosphodiesterase