156083-34-0

Basic information

• Product Name: tetrahydro-2-[[3-(2-ethynylphenyl)-2-propyn-1-yl]oxy]-2H-pyran
• Synonyms: tetrahydro-2-[[3-(2-ethynylphenyl)-2-propyn-1-yl]oxy]-2H-pyran
• CAS NO: 156083-34-0
• Molecular Weight: 240.302
• Mol File: 156083-34-0.mol

Chemical Properties

• CAS DataBase Reference: tetrahydro-2-[[3-(2-ethynylphenyl)-2-propyn-1-yl]oxy]-2H-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: tetrahydro-2-[[3-(2-ethynylphenyl)-2-propyn-1-yl]oxy]-2H-pyran(156083-34-0)
• EPA Substance Registry System: tetrahydro-2-[[3-(2-ethynylphenyl)-2-propyn-1-yl]oxy]-2H-pyran(156083-34-0)

Safety Data

• Hazardous Substances Data: 156083-34-0(Hazardous Substances Data)

Upstream product

• 6089-04-9 3-(tetrahydropyran-2'-yloxy)propyne 
• 583-55-1 1-Bromo-2-iodobenzene 
• 915237-87-5 tetrahydro-2-[[3-(2-bromophenyl)-2-propyn-1-yl]oxy]-2H-pyran 
• 915237-88-6 trimethyl-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenylethynyl}-silane 

Downstream Products

• 1421947-12-7 C₃₆H₃₃NO₄S 
• 1374583-36-4 C₂₂H₁₂S 
• 1374583-35-3 1,4-bis[2-(3-bromoprop-1-ynyl)phenyl]buta-1,3-diyne 
• 1163301-98-1 C₂₄H₁₈O₆S₂ 
• 1163301-97-0 2,2'-(buta-1,3-diyne-1,4-diyl)bis[(3-hydroxypropynyl)benzene] 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 91-57-6 2-Methylnaphthalene 
• 1163301-91-4 C₃₀H₃₀O₄ 
• 1163301-96-9 C₃₂H₃₀O₄ 
• 880362-21-0 1-(4-benzyloxy-3-hydroxy-1-butynyl)-2-(3-hydroxy-1-propynyl)benzene 
• 927439-27-8 methanesulfonic acid 3-(2-pent-4-en-1-ynyl-phenyl)-prop-2-ynyl ester 
• 927439-37-0 1-(3-azido-prop-1-ynyl)-2-pent-4-en-1-ynyl-benzene 
• 927439-25-6 3-(2-pent-4-en-1-ynyl-phenyl)-prop-2-yn-1-ol 
• 927439-23-4 2-[3-(2-pent-4-en-1-ynyl-phenyl)-prop-2-ynyloxy]-tetrahydro-pyran 

Relevant articles and documents

Reactivity of bispropargyl sulfones under basic conditions: Interplay between Garratt-Braverman and Schmittel/Myers-Saito cyclization pathway

The preference for Garratt-Braverman (GB) over Myers-Saito (MS) and Schmittel (SCM) cyclizations has recently been demonstrated in sulfones capable of undergoing all three of the processes. As the GB cyclization is a self-quenching process, there is a nee

Conformationally gated fragmentations and rearrangements promoted by interception of the bergman cyclization through intramolecular H-abstraction: A possible mechanism of auto-resistance to natural enediyne antibiotics?

A variety of fragmentations and rearrangements can follow Bergman cyclization in enediynes equipped with acetal rings mimicking the carbohydrate moiety of natural enediyne antibiotics of the esperamicine and calchiamicine families. In the first step of all these processes, intramolecular H-atom abstraction efficiently intercepts the p-benzyne product of the Bergman cyclization through a six-membered TS and transforms the p-benzyne into a new more stable radical. Depending on the substitution pattern and reaction conditions, this radical follows four alternative paths: (a) abstraction of an external hydrogen atom, (b) O-neophyl rearrangement which transposes O- and C-atoms of the substituent, (c) fragmentation of the O-C bond in the acetal ring, or (d) fragmentation with elimination of the appended acetal moiety as a whole. Experiments with varying concentrations of external H-atom donor (1,4-cyclohexadiene) were performed to gain further insight into the competition between intermolecular H-abstraction and the fragmentations. The Thorpe-Ingold effect in gem-dimethyl substituted enediynes enhances the efficiency of fragmentation to the extent where it cannot be prevented even by a large excess of external H-atom donor. These processes provide insight into a possible mechanism of unusual fragmentation of esperamicin A1 upon its Bergman cycloaromatization and lay foundation for a new approach for the conformational control of reactivity of these natural antitumor antibiotics. Such an approach, in conjunction with supramolecular constraints, may provide a plausible mechanism for resistance to enediyne antibiotics by the enediyne-producing microorganisms.

Design and synthesis of bisenediyne bissulfones and their reactivity under basic condition

A new class of bisenediyne bis sulfones has been synthesized. These molecules underwent cycloaromatization under basic conditions via isomerization to allene and were able to cleave ds-stranded plasmid DNA.

Synthesis of isoxazoline-fused bicyclic enediynes via intramolecular nitrile oxide-alkene cycloaddition

The intramolecular nitrile oxide-alkene cycloaddition has been studied in an enediyne system. It has been shown to be an efficient method for one-step synthesis of isoxazoline-fused bicyclic enediynes. The thermal reactivity of these enediynes is similar

Chemistry of enediynyl azides: Activation through a novel pathway

The spontaneous activation of a nonaromatic enediynyl azide under ambient conditions has been demonstrated. The aromatic enediyne followed the expected cycloaddition with the alkene in the neighbouring arm to form a stable bridged bicyclic enediyne. The R

Reaction of ene-bis(phosphinylallenes): [2+2] versus [4+2] cycloaddition

Reaction of ene-bis(phosphinylallenes), derived from ene-bis(propargyl alcohols) and chlorodiphenylphosphine, was investigated. Benzene-bridged bis(phosphinylallenes) exclusively gave intramolecular [2+2] cycloadducts in the presence of dimethyl fumarate