94383-67-2

Basic information

• Product Name: 1,5-Diphenylbicyclo[3.2.0]heptane
• Synonyms: 1,5-Diphenylbicyclo[3.2.0]heptane
• CAS NO: 94383-67-2
• Molecular Formula: C₁₉H₂₀
• Molecular Weight: 0
• Mol File: 94383-67-2.mol

Chemical Properties

• Boiling Point: 347.4°Cat760mmHg
• Flash Point: 174.7°C
• Appearance: /
• Density: 1.113g/cm³
• Vapor Pressure: 0.000108mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: 1,5-Diphenylbicyclo[3.2.0]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-Diphenylbicyclo[3.2.0]heptane(94383-67-2)
• EPA Substance Registry System: 1,5-Diphenylbicyclo[3.2.0]heptane(94383-67-2)

Safety Data

• Hazardous Substances Data: 94383-67-2(Hazardous Substances Data)

Usage

Abbreviation

DBH

Type of compound

Synthetic organic compound

Classification

Bicyclic hydrocarbon, polycyclic aromatic compound

Physical state

White crystalline solid at room temperature

Solubility

Insoluble in water

Primary use

Building block in the synthesis of pharmaceuticals and organic compounds

Stereochemical properties

Exhibits interesting stereochemical properties

Applications

Potential applications in medicinal chemistry and materials science

Use in coordination chemistry

Acts as a ligand

Use in asymmetric synthesis

Acts as a chiral auxiliary

InChI:InChI=1/C19H20/c1-3-8-16(9-4-1)18-12-7-13-19(18,15-14-18)17-10-5-2-6-11-17/h1-6,8-11H,7,12-15H2

Upstream product

• 27905-65-3 2,6-Diphenyl-1,6-heptadiene 
• 71-43-2 benzene 
• 6263-83-8 1,5-diphenyl-1,5-pentanedione 
• 2873-74-7 gloutaric dichloride 

Downstream Products

• 27905-65-3 2,6-Diphenyl-1,6-heptadiene 
• 157367-60-7 1,5-Diphenyl-6,7-dioxa-bicyclo[3.2.2]nonane 

Relevant articles and documents

Flavin Photocatalysts for Visible-Light [2+2] Cycloadditions: Structure, Reactivity and Reaction Mechanism

New photocatalysts from the flavin family were found to mediate the [2+2] photocycloaddition reaction. 3-Butyl-10-methyl-5-deazaflavin (3 a) and 1-butyl-7,8-dimethoxy-3-methylalloxazine (2 e), if irradiated by visible light, were shown to allow an efficie

Visible Light [2+2] Photocycloaddition Mediated by Flavin Derivative Immobilized on Mesoporous Silica

7,8-Dimethoxy-3-methylalloxazine was immobilized on mesoporous silica (MCM-41) to provide a heterogenized flavin photocatalyst. Thus, the prepared heterogeneous catalyst 2 was found to sensitize the visible light [2+2] cycloaddition of various types of di

Tailoring flavins for visible light photocatalysis: organocatalytic [2+2] cycloadditions mediated by a flavin derivative and visible light

A new application of flavin derivatives in visible light photocatalysis was found. 1-Butyl-7,8-dimethoxy-3-methylalloxazine, when irradiated by visible light, was shown to allow an efficient cyclobutane ring formation via an intramolecular [2+2] cycloaddition of both styrene dienes, considered as electron-rich substrates, and electron-poor bis(arylenones), presumably proceeding via an energy transfer mechanism.

Photoinduced Electron Transfer (PET) cyclization and photooxygenation of 2,6-diaryl-1,6-heptadienes and 2,7-diaryl-1,7-octadienes

The 2,6-diaryl-substituted 1,6-heptadienes 3a-c and the 2,7-diaryl-substituted 1,7-octadienes 4a-b were cleanly converted into the corresponding anellated cyclobutanes 5 and 6, resp., when irradiated under photoelectron-transfer conditions (9,10-dicyanoanthracene in acetonitrile). Only for 4c did the rearranged compound 7c become the dominant photoproduct. Oxygen trapping experiments with formation of endoperoxides 8, 9 were successful in the case of the electron-rich substrates 3b, c and 4c. VCH Verlagsgesellschaft mbH, 1996.

Electron-transfer induced intramolecular [2+2] cycloaddition of 2,6-diarylhepta-1,6-dienes

Intramolecular [2+2] cycloaddition of 2,6-diaryl-1,6-heptadienes 1a-c to bicycloheptanes 2 can be induced by electron-transfer photosensitization with 9,10-dicyanoanthracene. A stepwise mechanism involving cyclic 1,4-cation radical 3 has been proposed based on the trapping experiments.

A "frustrated" cope rearrangement: Thermal interconversion of 2,6-diphenylhepta-1,6-diene and 1,5-diphenylbicyclo[3.2.0]heptane

The title reaction constitutes a reliable model of a nonconcerted, diradical mechanism closely related to a Cope rearrangement. Its activation parameters relate to a transition state approximated by 1,5-diphenylcyclohepta-1,5-diyl (7). Force field calcula