176384-79-5

Basic information

• Product Name: 1-(3-hydroxy-1-propynyl)-2-iodobenzene
• Synonyms: 1-(3-hydroxy-1-propynyl)-2-iodobenzene
• CAS NO: 176384-79-5
• Molecular Weight: 258.058
• Mol File: 176384-79-5.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 1-(3-hydroxy-1-propynyl)-2-iodobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-hydroxy-1-propynyl)-2-iodobenzene(176384-79-5)
• EPA Substance Registry System: 1-(3-hydroxy-1-propynyl)-2-iodobenzene(176384-79-5)

Safety Data

• Hazardous Substances Data: 176384-79-5(Hazardous Substances Data)

Upstream product

• 615-43-0 2-iodophenylamine 
• 125812-44-4 2-(2-(hydroxymethyl)ethynyl)aniline 
• 253435-18-6 2-(3-(2-tetrahydropyranyloxy)-1-propynyl)-1-iodobenzene 
• 615-42-9 1,2-Diiodobenzene 
• 107-19-7 propargyl alcohol 

Downstream Products

• 156093-12-8 3-<2-(5-((tert-butyldimethylsilyl)oxy)-1-pentynyl)phenyl>-2-propyn-1-ol 
• 1137728-92-7 (S)-6-[2-(3-hydroxy-prop-1-ynyl)phenyl]-2-(toluene-4-sulfonylamino)-hex-5-ynoic acid methyl ester 
• 1137728-77-8 (R)-5-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-2-(toluene-4-sulfonylamino)-pent-4-ynoic acid methyl ester 
• 1334223-32-3 1-(3-azido-prop-1-ynyl)-2-iodo-benzene 

Relevant articles and documents

Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes

Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. We report a photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes. Quantum mechanical calculations (uM06-2X and DLPNO), including TD-DFT calculations, and experimental studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cla￠ radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. We anticipate that the use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity.

Palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides

A palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides is reported. Remarkably, the orderly insertion of isocyanides affords two types of valuable N-heterocyclic products (Z)-6-imino-4,6-dihydro-1H-furo[3,4-b]pyrrol-2-amines and (E)-5-iminopyrrolones in high yields. Systematic analysis of the reaction conditions indicates that the selectivity of these N-heterocyclic products can be controlled by ligands and temperature.

Memory of chirality in cascade rearrangements of enediynes

The cascade rearrangement of chiral enediynes 1c-e, involving successively 1,3-proton shift, Saito-Myers cyclization, 1,5-hydrogen atom transfer, and intramolecular coupling of the resulting biradical, proceeded at 80°C to form tri- and tetracyclic heterocycles possessing a quaternary stereogenic center with a very high level of memory of chirality.