202329-50-8

Basic information

• Product Name: hepta-1,6-dien-1-ylbenzene
• Synonyms: hepta-1,6-dien-1-ylbenzene
• CAS NO: 202329-50-8
• Molecular Weight: 172.27
• Mol File: 202329-50-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: hepta-1,6-dien-1-ylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: hepta-1,6-dien-1-ylbenzene(202329-50-8)
• EPA Substance Registry System: hepta-1,6-dien-1-ylbenzene(202329-50-8)

Safety Data

• Hazardous Substances Data: 202329-50-8(Hazardous Substances Data)

Upstream product

• 6814-64-8 methylenedimethyl sulfurane 
• 53847-18-0 6-phenyl-5-hexenal 
• 110-87-2 3,4-dihydro-2H-pyran 
• 4221-03-8 5-hydroxypentanal 
• 98078-15-0 6-phenylhex-5-en-1-ol 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 1204322-98-4 C₂₆H₂₆O₄S 
• 1334544-80-7 C₂₆H₂₈O₄S 
• 1334544-81-8 C₂₇H₂₂O₄S 
• 4392-24-9 Cinnamyl bromide 

Downstream Products

• 207986-38-7 2-(3-Oxiranyl-propyl)-3-phenyl-oxirane 
• 65825-74-3 3-methyl-2-phenylcyclohex-2-en-1-one 
• 15177-05-6 1-phenylhept-6-en-1-one 

Relevant articles and documents

Improvements and Applications of the Transition Metal-Free Asymmetric Allylic Alkylation using Grignard Reagents and Magnesium Alanates

Two new N-heterocyclic carbene (NHC) ligands have been synthesized and employed in the transition metal-free asymmetric allylic alkylation (AAA) mediated by Grignard reagents and magnesium alanates. The employment of these ligands showed high yields and improved regio- and enantioselectivity in the formation of tertiary and quaternary stereocenters. Moreover, the low catalyst loading (up to 0.3 mol%) and high scalability (up to 10 mmol) of this improved methodology provide a convenient access to biologically active compounds and synthetically valuable intermediates.

Enantioselective copper-catalysed allylic alkylation of cinnamyl chlorides by Grignard reagents using chiral phosphine-phosphite ligands

The copper(I)-catalysed SN2'-type allylic substitution of E-3-aryl-allyl chlorides (cinnamyl chlorides) using Grignard reagents represents a powerful method for the synthesis of compounds carrying a benzylic stereocentre. By screening a small library of modular chiral phosphine-phosphite ligands a new copper(I)-based catalyst system was identified which allows the performance of such reactions with exceptional high degrees of regio- and enantioselectivity. Best results were obtained using TADDOLderived ligands (3 mol%), copper(I) bromide?dimethyl sulfide (CuBr?SMe2) (2.5 mol%) and methyl tert-butyl ether (MTBE) as a solvent. Various (1- alkyl-allyl)benzene derivatives were prepared with up to 99% ee (GC) in isolated yields of up to 99%. In most cases the product contained less than 3% of the linear regioisomer (except for ortho-substituted substrates). Both electron-rich and electron-deficient cinnamyl chlorides were successfully employed. The absolute configuration of the products was assigned by comparison of experimental and calculated CD spectra. The substrates were prepared from the corresponding alcohols by reaction with thionyl chloride. Initially formed mixtures of regioisomeric allylic chlorides were homogenised by treatment with CuBr?SMe2 (2.5 mol%) in the presence of triphenyl phosphine (PPh3) (3 mol%) in MTBE at low temperature to give the pure linear isomers. In reactions with methylmagnesium bromide (MeMgBr) an ortho-diphenylphosphanyl-arylphosphite ligand with an additional phenyl substituent in ortho'-position at the aryl backbone proved to be superior. In contrast, best results were obtained in the case of higher alkyl Grignard reagents (such as ethyl-, n-butyl-, isopropyl-, and 3-butenylmagnesium bromides) with a related ligand carrying an isopropyl substituent in ortho'-position. The method was tested on a multimmol scale and is suited for application in natural product synthesis.