67451-62-1

Basic information

• Product Name: 3,5-Cyclohexadiene-1,2-diol, 3-bromo-, trans-
• CAS NO: 67451-62-1
• Molecular Formula: C6H7BrO2
• Molecular Weight: 191.024
• Mol File: 67451-62-1.mol
• Article Data: 30

Chemical Properties

• CAS DataBase Reference: 3,5-Cyclohexadiene-1,2-diol, 3-bromo-, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Cyclohexadiene-1,2-diol, 3-bromo-, trans-(67451-62-1)
• EPA Substance Registry System: 3,5-Cyclohexadiene-1,2-diol, 3-bromo-, trans-(67451-62-1)

Safety Data

• Hazardous Substances Data: 67451-62-1(Hazardous Substances Data)

Upstream product

• 108-86-1 bromobenzene 

Downstream Products

• 138769-97-8 (1S,2S)-1,2-dihydroxy-3-methylsulfanylcyclohexa-3,5-diene 
• 219655-88-6 (1S,6S)-2-Bromo-6-triisopropylsilanyloxy-cyclohexa-2,4-dienol 
• 1035055-69-6 C₁₄H₁₃BrO₃ 
• 140210-12-4 (1S,2R)-3-Phenylethynyl-cyclohexa-3,5-diene-1,2-diol 
• 1256603-72-1 C₃₂H₃₇NO₄Si 
• 1256603-57-2 C₂₁H₃₀O₇ 
• 1256603-58-3 C₂₁H₃₀O₇ 
• 1256603-70-9 C₃₁H₃₆O₄Si 
• 1256603-69-6 C₃₃H₃₉NO₄Si 
• 1025938-68-4 C₆H₈Br₂O₃ 
• 10284-63-6 pinitol 
• 3559-00-0 (-)-pinitol 
• 138430-37-2 (1S,2R,3S,6R)-6-Benzyloxycarbonylamino-1,2-O-isopropylidenecyclohex-4-ene-1,2,3-triol 
• 138448-92-7 3-(benzyloxycarbonyl)-1-bromo-5,6-O-isopropylidene-2-oxa-3-azabicyclo<2.2.2>oct-7-ene-5,6-diol 

Relevant articles and documents

Synthesis and biological evaluation of 10-benzyloxy-Narciclasine

A chemoenzymatic convergent synthesis of 10-benzyloxy narciclasine from bromobenzene was accomplished in 16 steps. The key transformations included toluene dioxygenase-mediated hydroxylation, nitroso Diels-Alder reaction and intramolecular Heck cyclization. The unnatural derivative of narciclasine was subjected to biological evaluation and its activity was compared to other C-10 and C-7 compounds prepared previously.

Site-Directed Mutagenesis Studies on the Toluene Dioxygenase Enzymatic System: Role of Phenylalanine 366, Threonine 365 and Isoleucine 324 in the Chemo-, Regio-, and Stereoselectivity

Toluene Dioxygenase (TDO) enzymatic complex has been widely used as a biocatalyst for the regio- and enantioselective preparation of cis-cyclohexadienediols, which are very important starting materials for organic synthesis. However, the lack of regio- and stereodiversity of the dioxygenation process by TDO and related dioxygenases constitutes a clear drawback when planning the use of these diols in synthetic schemes. In this work, we developed three TDO mutants in residues phenylalanine 366, threonine 365 and isoleucine 324, with the aim to alter the chemo-, regio- and stereoselectivity of the biotransformation of arenes. While no changes in the regioselectivity of the process were observed, dramatic variations in the chemo- and enantioselectivity were found for mutants I324F, T365N and F366 V in a substrate-dependent manner. (Figure presented.).

Aza and oxo Diels-Alder reactions using cis-cyclohexadienediols of microbial origin: Chemoenzymatic preparation of synthetically valuable heterocyclic scaffolds

Aza and oxo Diels-Alder reactions using enantiopure cis-cyclohexadienediols were studied. These dienediols were obtained from the biotransformation of monosubstituted arenes using bacterial dioxygenases (toluene and benzoate dioxygenases). Ethyl glyoxylate and its N-tosyl imine were used as dienophiles to afford the corresponding hetero Diels-Alder bicyclic adducts with excellent regio- and stereoselectivities. Quantum chemical calculations at the B3LYP/6-31+G(d,p) level of theory were performed to rationalize the observed selectivities especially the stereochemical aspects of the cycloadditions. The synthetic importance of these adducts is highlighted for the preparation of enantiopure 2,2,3,4,5,6-hexasubstituted piperidine and tetrahydropyran from toluene.