209858-52-6

Basic information

• Product Name: (1S,7S,10R,11S)-1-Ethynyl-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione
• CAS NO: 209858-52-6
• Molecular Weight: 311.297
• Mol File: 209858-52-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,7S,10R,11S)-1-Ethynyl-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,7S,10R,11S)-1-Ethynyl-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione(209858-52-6)
• EPA Substance Registry System: (1S,7S,10R,11S)-1-Ethynyl-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione(209858-52-6)

Safety Data

• Hazardous Substances Data: 209858-52-6(Hazardous Substances Data)

Upstream product

• 536-74-3 phenylacetylene 
• 138769-92-3 cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene 
• 591-50-4 iodobenzene 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 114763-29-0 (2R,3S)-2,3-dihydroxy-1-ethynylcyclohexa-4,6-diene 

Relevant articles and documents

Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes

Toluene dioxygenase-catalysed oxidation of mono-substituted benzene substrates (R = F, Cl, Br, I, Me, Et, CH2OAc, CH=CH2, C=CH, CF3, CN, OMe, OEt, SMe) in growing cultures of Pseudomonas putida UV4 yielded the corresponding cis-dihydrodiol metabolites. Palladium-catalysed cross-coupling of cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene with a range of tributyltin compounds provided a chemoenzymatic route to a further series of cis-dihydrodiol derivatives of monosubstituted benzenes (R = D, CH2CH=CH2, Bun, SEt, SPr1, SBu1, SPh, SC6H4Me-4). The enantiopurities and absolute configurations of the cis-dihydrodiols, obtained by both enzymatic and chemoenzymatic routes, were determined by several new methods including 1H NMR spectroscopic analysis of the bis-MTPA esters of the 4-phenyl-1,2,4-triazoline-3,5-dione cycloadducts, X-ray crystallography, circular dichroism spectroscopy and stereochemical correlation.