86342-79-2

Basic information

• Product Name: 2,6,10,16,20-Docosapentaene, 13-ethenyl-2,6,10,13,17,21-hexamethyl-, (6E,10E,16E)-
• CAS NO: 86342-79-2
• Molecular Formula: C30H50
• Molecular Weight: 410.727
• Mol File: 86342-79-2.mol

Chemical Properties

• CAS DataBase Reference: 2,6,10,16,20-Docosapentaene, 13-ethenyl-2,6,10,13,17,21-hexamethyl-, (6E,10E,16E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6,10,16,20-Docosapentaene, 13-ethenyl-2,6,10,13,17,21-hexamethyl-, (6E,10E,16E)-(86342-79-2)
• EPA Substance Registry System: 2,6,10,16,20-Docosapentaene, 13-ethenyl-2,6,10,13,17,21-hexamethyl-, (6E,10E,16E)-(86342-79-2)

Safety Data

• Hazardous Substances Data: 86342-79-2(Hazardous Substances Data)

Upstream product

• 29849-75-0 diphosphoric acid mono-[2t-((E)-4,8-dimethyl-nona-3,7-dienyl)-2c-methyl-3t-((1E,5E)-2,6,10-trimethyl-undeca-1,5,9-trienyl)-cycloprop-r-ylmethyl] ester 
• 4128-17-0 (2E,6E)-farnesyl acetate 
• 24163-93-7 farnesyl bromide 
• 6784-45-8 (2E,6E)-farnesyl chloride 
• 85611-33-2 (E)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate 

Relevant articles and documents

Mild TiIII- and Mn/ZrIV-catalytic reductive coupling of allylic halides: Efficient synthesis of symmetric terpenes

(Chemical Equation Presented) Two new efficient methods for the regioselective homocoupling of allylic halides using either catalytic Ti III or the combination Mn/ZrIV catalyst have been developed. The regio- and stereoselectivity of the process proved to increase significantly when the Mn/ZrIV catalyst is used as the coupling reagent and when cyclic substituted allylic halides are used as substrates. The use of Lewis acids such as collidine hydrochloride allowed the quantity of catalyst to be lowered up to 0.05 equiv. We have proved the utility of these protocols with the synthesis of different terpenoids such as (+)-β-onoceradiene (1), (+)-β-onocerine (2), squalene (5), and advanced key-intermediates in the syntheses of (+)-cymbodiacetal (3) and dimeric ent-kauranoids as xindongnin M (4a).

Regio- and Stereoselective Synthesis of 1,5-Dienes Using Allylic Barium Reagents

The highly α,α' selective and sterocontrolled homocoupling reaction of allylic halides was achieved using barium reagent.The double-bond geometry of the starting allylic chloride was completely retained.The α,α' cross-coupling products were also prepared stereospecifically and regioselectively by this method.

Highly Selective Homocoupling Reaction of Allylic Halides Using Barium Metal

The highly α,α' selective and stereocontrolled homocoupling reaction of allylic halides was achieved using barium reagent.The double-bond geometry of the starting allylic chloride was completely retained. α,α' Cross-coupling products were also prepared stereospecifically and regioselectively by this method.

Hexacarbonylmolybdenum(0)-Catalyzed Reductive Coupling of Allylic Acetates

The reaction of allylic acetates with zinc in the presence of a catalytic amount of hexacarbonylmolybdenum(0) led to reductive coupling for the formation of a 1,5-diene framework.Reductive coupling of nerolidyl acetate provided squalene and its isomers in high yield.

PALLADIUM-CATALYZED COUPLING OF ALLYLIC ACETATES WITH ZINC

Allylic acetates were coupled with zinc dust in the presence of a catalytic amount of to give the corresponding 1,5-dienes under mild conditions in high yields.Significant cosolvent effects were found with methanol or 1,2-ethanediol in tetrahydrofuran.

Reaction of Organic Halides with Chlorotris(triphenylphosphine)cobalt(I)

Reaction of various types of organic halides with a monovalent cobalt complex, chlorotris(triphenylphosphine)cobalt(I) is described.Reaction of benzylic monohalides, dihalides and trihalides with CoCl(Ph3P)3 gave a coupling product with formation of a carbon-carbon single bond, double bond and triple bond, respectively, under mild and non-basic conditions.Dehalogenation of non-benzylic vicinal dihalides with the reagent took place cleanly to give an olefin in high yield.Reductive coupling of allylic halides using the reagent afforded regioselectively a 1,5-diene with retention of the stereochemistry of the carbon-carbon double bond of the allylic halides used.By using this reaction, (E,E,E,E)-squalene was stereospecifically synthesized from (E,E)-farnesyl bromide.Reaction of halohydrins with CoCl(Ph3P)3 gave exclusively a ketone in the presence of an amine or olefin through an alkylcobalt intermediate.A 1,2-hydrogen shift is involved in this reaction.Keywords - chlorotris(triphenylphosphine)cobalt(I); coupling reaction; benzylic halides; allylic halides; synthesis of 1,5-diene; squalene; halohydrin; ketone synthesis.

REDUCTIVE COUPLING OF ALLYLIC HALIDES BY CHLOROTRIS(TRIPHENYLPHOSPHINE)COBALT(I)

Reactions of geranyl and farnesyl halide, and their geometrical isomers with chlorotris(triphenylphosphine)cobalt(I) gave the corresponding geometrically pure coupling products under mild and non-basic conditions.Squalenes were stereospecifically synthesized by this method.