80277-63-0

Basic information

• Product Name: E-5-methyl-3-hexen-2-yl p-nitrobenzoate
• CAS NO: 80277-63-0
• Molecular Weight: 263.293
• Mol File: 80277-63-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: E-5-methyl-3-hexen-2-yl p-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: E-5-methyl-3-hexen-2-yl p-nitrobenzoate(80277-63-0)
• EPA Substance Registry System: E-5-methyl-3-hexen-2-yl p-nitrobenzoate(80277-63-0)

Safety Data

• Hazardous Substances Data: 80277-63-0(Hazardous Substances Data)

Upstream product

• 146513-95-3 (rac,E)-5-methylhex-3-en-2-ol 
• 122-04-3 4-nitro-benzoyl chloride 
• 1669-43-8 (E)-4-isopropylbut-3-en-2-one 

Relevant articles and documents

Nucleophilic substitution of 5,5-dimethyl-2-cyclopentenyl derivatives. Lack of SN2' reaction

Treatment of tetramethyl-1,3-cyclobutadienone with two equivalents of allyl oxide anion at 140 deg C yields 2,2-dimethyl-4-pentenoic acid which is cyclized via the acid chloride whith aluminium chloride to 5,5-dimethyl-2-cyclopentenone 4.Reduction of 4 with aluminium hydride provides 5,5-dimethyl-2-cyclopentenol 1-OH which is pyrolyzed to 5,5-dimethyl-1,3-cyclopentadiene in dimethylsulfoxide.Reduction of 4 with tri-t-butoxyaluminium hydride at -70 deg C gives 2,2-dimethylcyclopentanone.The 2,6-dichlorobenzoate ester of 1-OH failed to yield SN2' products under a variety of conditions.The rate constants for solvolysis of the p-nitrobenzoate esters of 1-OH, 2-cyclopentenol and Z-2-methyl-4-hexene-3-ol in 80 percent ethanol at 80 deg C are 20.2, 523, and 0.63 x 1E-6s-1, respectively, and the main products of solvolysis are 5-ethoxy-3,3-dimethylcyclopentene, 3-ethoxycyclopentene, and E-2-ethoxy-5-methyl-3-hexene, respectively.There is steric hindrance to solvatation during ionization of the p-nitrobenzoate of 1-OH.