85217-72-7

Basic information

• Product Name: Carbonic acid, (2E)-3,7-dimethyl-2,6-octadienyl methyl ester
• Synonyms: (E)-3,7-dimethylocta-2,6-dien-1-yl methyl carbonate;geranyl carbonate;Carbonic acid,(2Z)-3,7-dimethyl-2,6-octadienyl methyl ester;geranyl methyl carbonate;Carbonic acid,(2E)-3,7-dimethyl-2,6-octadienyl methyl ester
• CAS NO: 85217-72-7
• Molecular Formula: C12H20O3
• Molecular Weight: 212.289
• Mol File: 85217-72-7.mol

Chemical Properties

• CAS DataBase Reference: Carbonic acid, (2E)-3,7-dimethyl-2,6-octadienyl methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbonic acid, (2E)-3,7-dimethyl-2,6-octadienyl methyl ester(85217-72-7)
• EPA Substance Registry System: Carbonic acid, (2E)-3,7-dimethyl-2,6-octadienyl methyl ester(85217-72-7)

Safety Data

• Hazardous Substances Data: 85217-72-7(Hazardous Substances Data)

Upstream product

• 79-22-1 methyl chloroformate 
• 624-15-7 geraniol 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 13058-12-3 ethyl 3,7-dimethyl-2,6-octadienoate 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 106-24-1 Geraniol 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 2436-90-0 dihydromyrcene 
• 2492-22-0 dihydromyrcene 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 3338-55-4 (Z)-ocimene 
• 68753-95-7 (2E,6E)-2,6-dimethyldeca-2,6-dien-10-trimethylsilyl-9-yne 
• 18069-17-5 2-methylglutaric acid 
• 56691-80-6 geranyl phenyl sulfone 
• 91940-11-3 (3,7-dimethylocta-1,6-diene-3-sulfonyl)benzene 
• 1604814-21-2 methyl (2Z,4E)-2-((dimethyl(phenyl)silyl)(phenyl)methylene)-5,9-dimethyldeca-4,8-dienoate 
• 1604814-22-3 methyl (2E,4E)-2-((dimethyl(phenyl)silyl)(phenyl)methylene)-5,9-dimethyldeca-4,8-dienoate 
• 3796-70-1 trans geranyl acetone 
• 35162-74-4 geranyl phenyl sulfide 
• 2436-90-0 (S)-(+)-dihydromyrcene 
• 689-67-8 pseudo-ionone 

Relevant articles and documents

Syntheses of perillene and natural congeners via Li2CuCl4-catalyzed cross-coupling reaction of allylic carbonates

Perillene is an essential ingredient in a Chinese patent drug and features some fascinating biological activities. We present herein an efficient pathway to perillene that hangs on the cross-coupling reaction of allylic carbonates with furfuryl Grignard r

Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization to Form Functionalized Hexahydropyrido[3,4- b]Indole

A fluoride-promoted intramolecular Sakurai allylation of geminal bis(silyl) enamide with indolenine has been developed. The reaction facilitates an efficient cyclization to give hexahydropyrido[3,4-b]indoles in good yields with high diastereoselectivity. The resulted cis, trans-stereochemistry further enables the ring-closing metathesis (RCM) reaction of two alkene moieties, giving a tetracyclic N-hetereocycle widely found as the core structure in akuammiline alkaloids.

Pd/BIPHEPHOS is an Efficient Catalyst for the Pd-Catalyzed S-Allylation of Thiols with High n-Selectivity

The Pd-catalyzed S-allylation of thiols with stable allylcarbonate and allylacetate reagents offers several advantages over established reactions for the formation of thioethers. We could demonstrate that Pd/BIPHEPHOS is a catalyst system which allows the transition metal-catalyzed S-allylation of thiols with excellent n-regioselectivity. Mechanistic studies showed that this reaction is reversible under the applied reaction conditions. The excellent functional group tolerance of this transformation was demonstrated with a broad variety of thiol nucleophiles (18 examples) and allyl substrates (9 examples), and could even be applied for the late-stage diversification of cephalosporins, which might find application in the synthesis of new antibiotics. (Figure presented.).

Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis

Palladium-catalyzed allylic substitution, or "Tsuji-Trost"reactions, can be run under micellar catalysis conditions featuring not only chemistry in water but also numerous combinations of reaction partners that require low levels of palladium, typically on the order of 1000 ppm (0.1 mol %). These couplings are further characterized by especially mild conditions, leading to a number of cases not previously reported in an aqueous micellar medium. Inclusion of diverse nucleophiles, such as N-H heterocycles, alcohols, dicarbonyl compounds, and sulfonamides is described. Intramolecular cyclizations further illustrate the broad utility of this process. In addition to recycling studies, a multigram scale example is reported, indicative of the prospects for scale up.

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The prenylation of peptides and proteins is an important post-translational modification observed in vivo. We report that the Pd-catalyzed Tsuji-Trost allylation with a Pd/BIPHEPHOS catalyst system allows the allylation of Cys-containing peptides and proteins with complete chemoselectivity and high n/i regioselectivity. In contrast to recently established methods, which use non-native connections, the Pd-catalyzed prenylation produces the natural n-prenylthioether bond. In addition, a variety of biophysical probes such as affinity handles and fluorescent tags can be introduced into Cys-containing peptides and proteins. Furthermore, peptides containing two cysteine residues can be stapled or cyclized using homobifunctional allylic carbonate reagents.

ORGANIC COMPOUNDS

The present invention refers to 3,7-dimethyloct-6-en-1-yl methyl carbonate and its use as fragrance ingredient. The invention further refers to fragrance compositions and fragranced articles comprising it.

Transesterification Reactions Catalyzed by a Recyclable Heterogeneous Zinc/Imidazole Catalyst

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Oxidative dimerization of 2-oxindoles promoted by KOtBu-I2: Total synthesis of (±)-folicanthine

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This paper describes a tunable and stereoselective dual catalytic system that uses copper and palladium reagents. This cooperative silylcupration and palladium-catalyzed allylation readily affords trisubstituted alkenylsilanes. Fine-tuning the reaction conditions allows selective access to one stereoisomer over the other. This new methodology tolerates different substituents on both coupling partners with high levels of stereoselectivity. The one-pot reaction involving a CuI/Pd0 cooperative dual catalyst directly addresses the need to develop more time-efficient and less-wasteful synthetic pathways.

Unique catalysis of gold nanoparticles in the chemoselective hydrogenolysis with H2: Cooperative effect between small gold nanoparticles and a basic support

Gold nanoparticles on hydrotalcite act as a heterogeneous catalyst for the chemoselective hydrogenolysis of various allylic carbonates to the corresponding terminal alkenes using H2 as a clean reductant. The combination of gold nanoparticles and basic supports elicited significantly unique and selective catalysis in the hydrogenolysis.