40596-76-7

Usage

InChI:InChI=1/C11H22O/c1-9(2)6-5-7-10(3)8-11(4)12/h6,10-12H,5,7-8H2,1-4H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 2385-77-5 (R)-Citronellal 
• 75-16-1 methylmagnesium bromide 
• 106-23-0 3,7-dimethyl-oct-6-enal 

Downstream Products

• 3664-64-0 rac-4,8-dimethyl-7-nonen-2-one 

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.

General, Auxiliary-Enabled Photoinduced Pd-Catalyzed Remote Desaturation of Aliphatic Alcohols

A general, efficient, and site-selective visible light-induced Pd-catalyzed remote desaturation of aliphatic alcohols into valuable allylic, homoallylic, and bis-homoallylic alcohols has been developed. This transformation operates via a hybrid Pd-radical mechanism, which synergistically combines the favorable features of radical approaches, such as a facile remote C-H HAT step, with that of transition-metal-catalyzed chemistry (selective β-hydrogen elimination step). This allows achieving superior degrees of regioselectivity and yields in the desaturation of alcohols compared to those obtained by the state-of-the-art desaturation methods. The HAT at unactivated C(sp3)-H sites is enabled by the easily installable/removable Si-auxiliaries. Formation of the key hybrid alkyl Pd-radical intermediates is efficiently induced by visible light from alkyl iodides and Pd(0) complexes. Notably, this method requires no exogenous photosensitizers or external oxidants.

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.

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.

CATALYTIC EXTENDED DOUBLE BOND MIGRATION WITH RETENTION OF CONFIGURATION: A "ZIP-REACTION"

(+) Citronellol was catalytically isomerized by Fe(CO)5 into (+) dihydrocitronellal with partial retention of configuration: the optical yield was 16 +/- 1 percent at 140 deg C.Isolation of partially isomerized intermediates and use of citronellol deuterated at various positions allowed a clear description of the reaction mechanism as a succession of 1,3 hydrogen shifts.The observed partial retention of configuration suggests that full 1,7 isomerization occurs before metal-olefin dissociation occurs even once.