84284-70-8

Usage

Uses

Used in Organic Synthesis:
4'-Benzyloxyphenyl acetylene is used as a chemical reagent for various organic synthesis processes due to its ability to participate in alkyne addition and Sonogashira coupling reactions. These reactions are crucial for constructing complex organic molecules and are widely used in the synthesis of natural products and pharmaceutical agents.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4'-benzyloxyphenyl acetylene is used as a building block for the development of new drugs. Its structural features allow for the creation of diverse medicinal compounds with potential therapeutic applications.
Used in Agrochemical Development:
Similarly, in agrochemicals, 4'-benzyloxyphenyl acetylene serves as a key intermediate in the synthesis of various agrochemical products, contributing to the development of effective crop protection agents and other agricultural chemicals.
Used as a Versatile Intermediate:
The ease of removing the benzyloxy group under mild conditions makes 4'-benzyloxyphenyl acetylene a versatile intermediate in organic chemistry. This property is particularly useful for the synthesis of a wide range of organic compounds, where the benzyloxy group can be selectively removed to yield the desired product.

InChI:InChI=1/C15H12O/c1-2-13-8-10-15(11-9-13)16-12-14-6-4-3-5-7-14/h1,3-11H,12H2

Upstream product

• 340322-86-3 2-[4-(benzyloxy)phenyl]-1-ethynyl(trimethyl)silane 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 27491-70-9 dimethyl diazomethylphosphonate 
• 114943-73-6 2-(4-Benzyloxyphenyl)-1,1-dibromoethylene 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 558-13-4 carbon tetrabromide 
• 100-39-0 benzyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 152915-78-1 C₁₈H₁₈O₂ 
• 540-38-5 p-Iodophenol 
• 88075-18-7 4-(2-(trimethylsilyl)ethynyl)phenol 
• 61439-59-6 2-(4-benzyloxyphenyl)ethanol 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 100-51-6 benzyl alcohol 

Downstream Products

• 1030829-56-1 ethyl 3-[4-(benzyloxy)phenyl]prop-2-ynoate 
• 475560-82-8 2,5-bis[(4-benzyloxyphenyl)ethynyl]-3,4-dibromothiophene 
• 877058-67-8 7-benzyl-2-(4-benzyloxy-phenyl)-3-phenyl-7H-furo[2,3-b]pyridin-4-one 
• 941574-05-6 C₂₉H₂₄O₅S 
• 953414-66-9 C₂₀H₁₅BrN₂O 
• 821798-77-0 tributyl[1-(4-benzyloxyphenyl)vinyl]stannane 
• 821798-73-6 1-benzyloxy-4-(1-iodovinyl)benzene 
• 1055324-11-2 4-[4-(benzyloxy)phenyl]-1-[(4R,6R)-2,2-dimethyl-4-tridecyl-1,3-dioxan-4-yl]-3-butyn-2-ol 
• 1192064-53-1 4-(4-(benzyloxy)phenyl)-1,2,3-triazole 
• 1172101-95-9 (3S,5S)-1-[4-(benzyloxy)phenyl]-5-tert-butyldiphenylsilanyloxy-1,7-phenylhept-1-yn-3-ol 
• 1172101-94-8 (3R,5S)-1-[4-(benzyloxy)phenyl]-5-tert-butyldiphenylsilanyloxy-1,7-phenylhept-1-yn-3-ol 
• 1220512-55-9 (5R,7R)-1-[4-(benzyloxy)phenyl]-5,7-bis{[(tert-butyl)(dimethyl)silyl]oxy}icos-1-yn-3-one 
• 1257078-89-9 4-((4-(benzyloxy)phenyl)ethynyl)-2-chloropyrimidine 
• 1310328-33-6 2-[6-(4-benzyloxyphenyl)-2,3-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl]propan-2-ol 

Relevant academic research and scientific papers

Cu-mediated or metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents

A novel copper-mediated or transition-metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents was described. The outcomes of these reactions were found to be highly dependent on the reaction conditions and

Synthesis of alkynes under dry reaction conditions

An easy synthetic method was developed under dry reaction conditions for the preparation of terminal alkynes from 1,1-dibromoalkenes and in the presence of succinimide which acts as a nucleophile and proton donor. It was demonstrated with the synthesis of a broad spectrum of terminal alkynes and extended to synthesize internal alkynes under tandem reaction conditions.

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).

First Synthesis of the [5-5-6-6] Tetracyclic Framework of Spiropreussione B

Rapid synthesis of the [5-5-6-6] tetracyclic system in the spirobionaphthalene natural product spiropreussione B was achieved. An intramolecular, thermal dehydrogenative Diels–Alder reaction was employed as the key step. Furthermore, this approach was extended to generate a library of structurally novel linear tetracyclic systems of spiropreussione B in a highly efficient manner. This report constitutes the first synthetic approach to the spiropreussione B natural product.

ANTIBACTERIAL AGENT

An antibacterial agent comprising a compound represented by the following general formula (I), which can exhibit potent antibacterial activity against bacteria that have acquired resistance to quinolones (in the formula, R1 and R4 re

Total synthesis of Daphnodorin A

A total synthesis of Daphnodorin A, a member of the Daphnodorins, was accomplished. Key features of the synthetic strategy include construction of 2-substituted-3-functionalized benzofuran via intramolecular Heck reaction and a mild Barton-McCombie deoxyg

Reactivity switch enabled by counterion: Highly chemoselective dimerization and hydration of terminal alkynes

A counterion-controlled reactivity tuning in Pd-catalyzed highly chemoselective and regioselective dimerization and hydration of terminal alkynes is reported. The use of acetate as counterion favors the formation of an alkenyl alkynyl palladium intermediate which forms hitherto less reported 1,3-diaryl-substituted conjugated enynes after reductive elimination. Using chloride, which is a better leaving group, leads to anion exchange on the alkenylpalladium intermediate with hydroxide which after reductive elimination and tautomerization delivered the hydration products.

An alternative role for acetylenes: Activation of fluorobenzenes toward nucleophilic aromatic substitution

Acetylenes are increasingly versatile functional groups for a range of complexity-building organic transformations and for the construction of desirable molecular architectures. Herein we disclose a previously underappreciated aspect of arylacetylene reac

New series of AB2-type hyperbranched polytriazoles derived from the same polymeric intermediate: Different endcapping spacers with adjustable bulk and convenient syntheses via click chemistry under copper(I) catalysis

In this article, according to the concept of "suitable isolation group," six new AB2-type polytriazoles containing azo-chromophore moieties, derived from the same hyperbranched polymer intermediate, were successfully prepared through click reac

HIF-1α inhibitors: Synthesis and biological evaluation of novel moracin O and P analogues

The natural products moracins O and P exhibited potent in vitro inhibitory activity against hypoxia-inducible factor (HIF-1), which is a key mediator during adaptation of cancer cells to tumour hypoxia. Systematic variations of the structures of benzofuran type moracins were made and structure-activity relationship analysis showed the importance of the 2-arylbenzofuran ring and the (R)-configuration of the core scaffold. Further evaluation of the representative compound 5 showed its inhibitory effect on HIF-1α protein accumulation and target gene expression under hypoxia.