81699-44-7

Basic information

• Product Name: 1,2-Dioxin, 3,6-dihydro-3-methyl-6-phenyl-
• CAS NO: 81699-44-7
• Molecular Formula: C11H12O2
• Molecular Weight: 176.215
• Mol File: 81699-44-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,2-Dioxin, 3,6-dihydro-3-methyl-6-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dioxin, 3,6-dihydro-3-methyl-6-phenyl-(81699-44-7)
• EPA Substance Registry System: 1,2-Dioxin, 3,6-dihydro-3-methyl-6-phenyl-(81699-44-7)

Safety Data

• Hazardous Substances Data: 81699-44-7(Hazardous Substances Data)

Upstream product

• 1029944-11-3 (3E)-1-phenyl-1,3-pentadiene 
• 3909-96-4 (1E,3E)-1-phenyl-1,3-pentadiene 
• 1608-27-1 1-phenylpenta-1,3-diene 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 1608-27-1 ((1E)-penta-1,3-dien-1-yl)benzene 

Downstream Products

• 34721-89-6 2-methyl-5-phenyl-furan 
• 5069-26-1 2-methyl-5-phenylthiophene 
• 3042-21-5 2-methyl-5-phenyl-1H-pyrrole 
• 300346-84-3 (E)-4-hydroxy-1-phenyl-2-penten-1-one 
• 300346-91-2 (Z)-4-hydroxy-1-phenyl-2-penten-1-one 
• 583-05-1 1-phenylpentane-1,4-dione 

Relevant articles and documents

A concise route to β-cyclopropyl amino acids utilizing 1,2-dioxines and stabilized phosphonate nucleophiles

(Chemical Equation Presented) 1,2-Dioxines react with glycine-derived phosphonate nucleophiles via a multistep cascade reaction to give β-cyclopropyl amino acid derivatives in good yield with excellent control of the cyclopropane stereocentres. The cyclopropyl ketones were oxidized to the corresponding carboxylic esters using Baeyer-Villiger conditions. Standard deprotection protocols produced a series of known β-cyclopropyl amino acids that are selective and potent agonists or antagonists of the metabotropic glutamate receptors in excellent yields.

Tetraphenylporphine-sensitized photooxygenation of (E,E)- and (E,Z)-1- aryl-1,3-pentadienes generating cis-endoperoxides

Photooxygenation of either (E,E)- or (E,Z)-1-aryl-1,3-pentadienes (1a- c) sensitized with tetraphenylporphine (TPP) in benzene gave almost all cis- endoperoxides (2a-c) (cis-3-aryl-6-methyl-1,2-dioxacyclohex-4-enes) in good yields. A time course study of photooxygenation of (E,Z)-rich dienes measured by 1H NMR showed that singlet oxygen added exclusively to (E,E)-dienes converted from (E,Z)-dienes by photoinduced isomerization, and both rates increased when electron-donating groups were attached to the aryl group. A concerted [4 + 2] cycloaddition mechanism is suggested by the exclusive formation of cis-endoperoxides from (E,E)-dienes, despite the small energy difference between cis- and trans-endoperoxides calculated by ab initio methods. Some experiments were made to explore the observed isomerization.

SENSITIZED PHOTO-OXYGENATION OF ACYCLIC CONJUGATED DIENES

Sensitized photo-oxygenation of a wide variety of acyclic 1,3-dienes was investigated.The 1,4-cycloaddition of singlet oxygen to acyclic conjugated dienes was closely related to the thermal Diels-Alder reaction in stereospecificity, and steric and electronic effects of substituents.Reactivity order of singlet oxygen toward conjugated dienes and isolated C-C double bonds was exhibited as follows: trisubstituted monoolefins > 2-substituted 1,3-dienes > disubstituted mono-olefins.