58558-13-7

Basic information

• Product Name: (2E)-3,7-dimethyl-2,6-octadienoyl chloride
• Synonyms: (2E)-3,7-dimethyl-2,6-octadienoyl chloride
• CAS NO: 58558-13-7
• Molecular Weight: 186.681
• Mol File: 58558-13-7.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (2E)-3,7-dimethyl-2,6-octadienoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3,7-dimethyl-2,6-octadienoyl chloride(58558-13-7)
• EPA Substance Registry System: (2E)-3,7-dimethyl-2,6-octadienoyl chloride(58558-13-7)

Safety Data

• Hazardous Substances Data: 58558-13-7(Hazardous Substances Data)

Upstream product

• 4698-08-2 (E)-geranic acid 

Downstream Products

• 1134607-84-3 (E)-N-benzyl-3,7-dimethylocta-2,6-dienamide 
• 1473417-84-3 C₁₉H₂₃NO₃ 
• 17015-63-3 (S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene 
• 1473417-85-4 C₂₁H₂₇NO₃ 
• 1473417-87-6 C₂₁H₂₇NO₃ 

Relevant articles and documents

Synthesis of Terpenes Containing the Bicycloheptane Ring System by the Intramolecular Cycloaddition Reaction of Vinylketenes with Alkenes. Preparation of Chrysanthenone, β-Pinene, β-cis-Bergamotene, β-trans-Bergamotene, β-Copaene, and β-Ylangene and Lemnalol

Treatment of geranoyl chloride (20) with triethylamine in toluene at reflux gave the vinylketene 21 which underwent a cycloaddition to give 7,7-dimethyl-2-methylenebicycloheptan-6-one (24) in 43percent yield.Isomerization over Pd gave chrysanthenone (6) in quantitative yield.Wolf-Kischner reduction gave β-pinene (5) in 70percent yield.A similar sequence of reactions starting from (Z,E)- and (E,E)-farnesoyl chloride gave ketones 51 and 57, which were converted to β-cis-bergamotene (8) and β-trans-bergamotene (9), respectively. β-Copaene (10) and β-ylangene (11) were prepared from 57 by a three-step sequence.Treatment of the imidazole 59 with tri-n-butyltin hydride in toluene at reflux gave a 46percent yield of a 1:1 mixture of 10 and 11.Selenium dioxide oxidation of 11 gave the antitumor agent lemnalol.The mechanisms of the regiospecific ketene generation and the cycloaddition reaction have been explored, and the reactivity of the novel bicycloheptanones has been examined.

Iron-Catalyzed, Fluoroamide-Directed C-H Fluorination

This communication describes a mild, amide-directed fluorination of benzylic, allylic, and unactivated C-H bonds mediated by iron. Upon exposure to a catalytic amount of iron(II) triflate (Fe(OTf)2), N-fluoro-2-methylbenzamides undergo chemoselective fluorine transfer to provide the corresponding fluorides in high yield. The reaction demonstrates broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic and computational experiments suggest that the reaction proceeds through short-lived radical intermediates with F-transfer mediated directly by iron.

GGA AND GGA DERIVATIVES COMPOSITIONS THEREOF AND METHODS FOR TREATING NEURODEGENERATIVE DISEASES INCLUDING PARALYSIS INCLUDING THEM

This invention relates to geranylgeranyl acetone (GGA) derivatives and the use of GGA, its isomers, and GGA derivatives in methods for inhibiting neural death, increasing neural activity, increasing axon growth and cell viability, and increasing the survival rate of subjects administered the GGA or GGA derivatives.