1510816-04-2

Basic information

• Product Name: 7-[3-(benzyloxy)prop-1-yn-1-yl]-9-tosyl-6,8,9,10-tetrahydro-1H,4H-1,3a-ethenoisochromeno[5,4-ef]isoindole
• Synonyms: 7-[3-(benzyloxy)prop-1-yn-1-yl]-9-tosyl-6,8,9,10-tetrahydro-1H,4H-1,3a-ethenoisochromeno[5,4-ef]isoindole
• CAS NO: 1510816-04-2
• Molecular Weight: 535.664
• Mol File: 1510816-04-2.mol

Chemical Properties

• CAS DataBase Reference: 7-[3-(benzyloxy)prop-1-yn-1-yl]-9-tosyl-6,8,9,10-tetrahydro-1H,4H-1,3a-ethenoisochromeno[5,4-ef]isoindole(CAS DataBase Reference)
• NIST Chemistry Reference: 7-[3-(benzyloxy)prop-1-yn-1-yl]-9-tosyl-6,8,9,10-tetrahydro-1H,4H-1,3a-ethenoisochromeno[5,4-ef]isoindole(1510816-04-2)
• EPA Substance Registry System: 7-[3-(benzyloxy)prop-1-yn-1-yl]-9-tosyl-6,8,9,10-tetrahydro-1H,4H-1,3a-ethenoisochromeno[5,4-ef]isoindole(1510816-04-2)

Safety Data

• Hazardous Substances Data: 1510816-04-2(Hazardous Substances Data)

Upstream product

• 1510816-15-5 N,N-bis[6-(benzyloxy)hexa-2,4-diyn-1-yl]-4-methylbenzenesulfonamide 
• 67-63-0 isopropyl alcohol 

Relevant articles and documents

Mechanism of the reactions of alcohols with o-benzynes

We have studied reactions of secondary and primary alcohols with benzynes generated by the hexadehydro-Diels-Alder (HDDA) reaction. These alcohols undergo competitive addition vs dihydrogen transfer to produce aryl ethers vs reduced benzenoid products, respectively. During the latter process, an equivalent amount of oxidized ketone (or aldehyde) is formed. Using deuterium labeling studies, we determined that (i) it is the carbinol C-H and adjacent O-H hydrogen atoms that are transferred during this process and (ii) the mechanism is consistent with a hydride-like transfer of the C-H. Substrates bearing an internal trap attached to the reactive, HDDA-derived benzyne intermediate were used to probe the kinetic order of the alcohol trapping agent in the H2-transfer as well as in the alcohol addition process. The H2-transfer reaction is first order in alcohol. Our results are suggestive of a concerted H2-transfer process, which is further supported by density functional theory (DFT) computational studies and results of a kinetic isotope effect experiment. In contrast, alcohol addition to the benzyne is second order in alcohol, a previously unrecognized phenomenon. Additional DFT studies were used to further probe the mechanistic aspects of the alcohol addition process.

Hydroarylation of arynes catalyzed by silver for biaryl synthesis

A new biaryl synthesis via silver-catalyzed hydroarylation of arynes from acyclic building blocks with unactivated arenes in intra- and intermolecular manners has been developed. The previously observed Diels-Alder reactions of arynes with arene were not observed under the current silver-catalyzed conditions. Deuterium scrambling and DFT calculations suggest a stepwise electrophilic aromatic substitution mechanism through the formation of a Wheland-type intermediate followed by a water-catalyzed proton transfer in the final step of the hydroarylation.

Dichlorination of (hexadehydro-diels-alder generated) benzynes and a protocol for interrogating the kinetic order of bimolecular aryne trapping reactions

The efficient dichlorination of benzynes prepared by the hexadehydro-Diels-Alder (HDDA) reaction is reported. Cycloisomerization of a triyne substrate in the presence of dilithium tetrachlorocuprate is shown to provide dichlorinated products A by capture