3664-64-0

Usage

InChI:InChI=1/C11H20O/c1-9(2)6-5-7-10(3)8-11(4)12/h6,10H,5,7-8H2,1-4H3

Upstream product

• 40596-76-7 4,8-dimethyl-7-nonen-2-ol 
• 65890-37-1 (±)-4,8-dimethylnon-7-en-1-yne 
• 27539-94-2 (3E)-4,8-dimethylnona-3,7-dien-2-one 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 32659-21-5 ethyl (E)-3,7-dimethylocta-2,6-dienoate 
• 27575-61-7 (3Z)-4,8-dimethylnona-3,7-dien-2-one 
• 502-47-6 racemic citronellic acid 
• 506-82-1 dimethylcadmium 
• 106-26-3 cis-3,7-dimethyl-2,6-octadienal 
• 124931-18-6 (E)-3,7-Dimethyl-octa-2,6-dienoic acid methoxy-methyl-amide 
• 81535-53-7 (Z)-methyl-4-(4-methyl-3-pentenyl)but-3-en-2-ol 
• 853065-81-3 1-methylgeraniol 

Downstream Products

• 4706-89-2 2,4-dimethylcumene 
• 111963-98-5 3-isopropenyl-6-methylcycloheptanone 
• 76189-17-8 (1R,2R,5S)-2-Isopropenyl-1,5-dimethyl-cyclohexanol 
• 76156-38-2 (1R,2S,5R)-2-Isopropenyl-1,5-dimethyl-cyclohexanol 

Relevant academic research and scientific papers

Primary Anion–π Catalysis of Epoxide-Opening Ether Cyclization into Rings of Different Sizes: Access to New Reactivity

The concept of anion–π catalysis focuses on the stabilization of anionic transition states on aromatic π surfaces. Recently, we demonstrated the occurrence of epoxide-opening ether cyclizations on aromatic π surfaces. Although the reaction proceeded through unconventional mechanisms, the obtained products are the same as those from conventional Br?nsted acid catalysis, and in agreement with the Baldwin selectivity rules. Different mechanisms, however, should ultimately lead to new products, a promise anion–π catalysis has been reluctant to live up to. Herein, we report non-trivial reactions that work with anion–π catalysis, but not with Br?nsted acids, under comparable conditions. Namely, we show that the anion–π templated autocatalysis and epoxide opening with alcoholate–π interactions can provide access to unconventional ring chemistry. For smaller rings, anion–π catalysis affords anti-Baldwin oxolanes, 2-oxabicyclo[3.3.0]octanes, and the expansion of Baldwin oxetanes by methyl migration. For larger rings, anion–π templated autocatalysis is thought to alleviate the entropic penalty of folding to enable disfavored anti-Baldwin cyclizations into oxepanes and oxocanes.

Asymmetric conjugate reduction of α,β-unsaturated ketones and esters with chiral rhodium(2,6-bisoxazolinylphenyl) catalysts

New asymmetric conjugate reduction of β,β-disubstituted α,β-unsaturated ketones and esters was accomplished with alkoxylhydrosilanes in the presence of chiral rhodium(2,6-bisoxazolinylphenyl) complexes in high yields and high enantioselectivity. (E)-4-Phenyl-3-penten-2- one and (E)-4-phenyl-4-isopropyl-3-penten-2-one were readily reduced at 60°C in 95% ee and 98 % ee, respectively, by 1 mol % of catalyst loading. (EtO) 2MeSiH proved to be the best hydrogen donor of choice. tert-Butyl (E)-β-methylcinnamate and β-isopropylcinnamate could also be reduced to the corresponding dihydrocinnamate derivatives up to 98% ee.

Cp*Ru(PN) complex-catalyzed isomerization of allylic alcohols and its application to the asymmetric synthesis of muscone

Highly efficient isomerization of allylic alcohols into saturated carbonyls is accomplished using the catalyst system of Cp*RuCl[Ph2P(CH2)2NH2-κ2-P,N]-KOt-Bu (Cp* = η5-C5(CH3)5) under mild conditions. Mechanistic consideration based on isotope-labeling experiments indicated the present reaction is applicable to the asymmetric isomerization of racemic sec-allylic alcohols with a prochiral olefin via dynamic kinetic resolution. A concise asymmetric synthesis of muscone has been achieved, where the asymmetric isomerization using an optically active ligand is a key reaction. Copyright

Catalytic Conversions in Water. Part 23: Steric Effects and Increased Substrate Scope in the Palladium-Neocuproine Catalyzed Aerobic Oxidation of Alcohols in Aqueous Solvents

The steric influence of substituents on the 2-and 9-positions of phenanthroline in the (2,9-R2-1,10-phenanthroline)palladium(II)- catalyzed aerobic oxidation of 2-hexanol was investigated by means of high throughput experimentation. (Neocuproine)Pd-(OAc)2 (R=CH 3) was found to be a highly active catalyst for alcohol oxidation in 1:1 water/DMSO mixtures. The catalyst is unique in that it tolerates water, polar co-solvents and a wide variety of functional groups in the alcohol. Turn-over frequencies of > 1500 h-1 were achieved and a series of alcohols was oxidised with 0.1 to 0.5 mol % of catalyst.

On the mechanism of carbohydroxypalladation of enynes. Additional insights on the cyclization of enynes with electrophilic metal complexes

Different mechanisms have been proposed for the cyclization of enynes catalyzed by electrophilic metal halides or complexes. We present evidence to indicate that the previously reported "carbohydroxypalladation" and the "hydroxycyclization catalyzed by PtII" are closely related reactions. Thus, palladium complexes formed in situ from PdCl2 and trisulfonated phosphane TPPTS or cyclic phosphite P(OCH2)3CEt as the ligands catalyze the methoxy- or hydroxycyclization of enynes with selectivities similar to those observed with PtII complexes. Deuteration studies indicate that activation of the alkyne by PdII promotes an anti-addition of the alkene. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Regio- and Stereoselective Hydrogenation of Conjugated Carbonyl Compounds via Palladium Assisted Hydrogen Transfer by Ammonium Formate

Excellent regio- and stereoselectivity has been achieved in the hydrogenation of C=C bond conjugated to carbonyl group in presence of olefin by ammonium formate/Pd-C system.

Syntheses and Growth Retarding Activity of Trialkylammonium Compounds from Citronellal

N,N,N-Trimethyl-5,9-dimethyl-2,8-decadienylammonium iodide (VI), N,N,N-trimethyl-2,5,9-trimethyl-2,8-decadienylammonium iodide (XI), N,N-diethyl-N-methyl-3,7-dimethyl-6-octenylammonium iodide (XIII), N,N,N-triethyl-3,7-dimethyl-6-octenylammonium iodide (XIV), N,N-diethyl-N-n-butyl-3,7-dimethyl-6-octenylammonium iodide (XV), N,N-diethyl-N-methyl-3,7-dimethyl-6-octenylammonium cyanide (XVI) and N,N,N-trimethyl-1,3,7-trimethyl-6-octenylammonium iodide (XX) have been prepared and examined as plant growth retardants.These compounds inhibit root formation in hypocotyl cuttings of Phaseolus aureus.

Ring Opening of Oxiranes by Trimethylsilyl Trifluoromethanesulfonate

Trimethylsilyl trifluoromethanesulfonate promotes ring opening reactions of oxirane derivatives.The reaction course is highly affected by the structures and substitution pattern of the substrates.Tetra-, tri, and 2,2-disubstituted oxiranes and simple cycloalkene oxides are converted to the corresponding allylic alcohol trimethylsilyl ethers.The overall transformation is interpreted in terms of trans addition of the silyl trifluoromethanesulfonate to the oxirane ring followed by base-promoted anti elimination of a trifluoromethanesulfonic acid element. 2,3-dialkyl- or monoalkyloxiranes isomerize to the corresponding ketones and aldehydes, respectively. (Z)-Cyclooctene oxide undergoes the transannular reaction to give endo-cis-2-trimethylsiloxybicyclooctane.The reaction of 6-methyl-5-hepten-2-one oxide produces 2,2,6-trimethyl-3-trimethylsiloxy-3,4-dihydro-2H-pyran. 1,2-Methyl migration takes place in the reaction of (E)-3α-t-butyldimethylsiloxy-5α-pregnene 17α,20-oxide to afford 3α-t-butyldimethylsiloxy-17β-methyl-17α--18-nor-5α-androst-13(14)-ene. α-Pinene oxide gives trans-carveol trimethylsilyl ether.