2216-87-7

Usage

Chemical Properties

Colorless transparent liquid

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 1788, 1972 DOI: 10.1021/ja00760a084Tetrahedron Letters, 20, p. 321, 1979 DOI: 10.1016/S0040-4039(01)85960-8

InChI:InChI=1/C11H22O/c1-3-5-6-7-8-9-10-11(12)4-2/h3-10H2,1-2H3

Upstream product

• 60-29-7 diethyl ether 
• 10385-09-8 N,N-diethyl nonanamide 
• 925-90-6 ethylmagnesium bromide 
• 71138-64-2 3-methyleneundecane 
• 60212-29-5 undec-2-yne 
• 111-66-0 oct-1-ene 
• 123-38-6 propionaldehyde 
• 94-36-0 dibenzoyl peroxide 
• 112-05-0 nonanoic acid 
• 802294-64-0 propionic acid 
• 71-43-2 benzene 
• 75-91-2 tert.-butylhydroperoxide 
• 79090-61-2 3-undecanol 
• 143-33-9 sodium cyanide 

Downstream Products

• 79090-61-2 3-undecanol 
• 1472-09-9 n-octylcyclopropane 
• 124-07-2 Octanoic acid 
• 79090-61-2 (S)-undecan-3-ol 
• 107494-37-1 (R)-undecan-3-ol 

Relevant academic research and scientific papers

The radical-chain addition of aldehydes to alkenes by the use of N-hydroxyphthalimide (NHPI) as a polarity-reversal catalyst

Hydroacylation of simple alkenes with aldehydes via a radical process was successfully achieved by the use of N-hydroxyphthalimide (NHPI) as a polarity-reversal catalyst. Thus, 5-tridecanone was obtained by the reaction of oct-1-ene with pentanal in the presence of small amounts of NHPI and dibenzoyl peroxide (BPO).

Sodium Bromide-Catalyzed Oxidation of Secondary Benzylic Alcohols Using Aqueous Hydrogen Peroxide as Terminal Oxidant

A halide salt, hydroperoxide and AcOH catalyst system was applied to the oxidation of secondary benzylic alcohols. This simple system can be applied to a variety of secondary benzylic alcohols and scaled up for gram-scale preparation. High secondary benzylic alcohol selectivity of the present method is demonstrated in hydroxyketone synthesis. Based on several experimental results, a catalytic cycle for our oxidation is proposed.

Borohydride-mediated radical addition reactions of organic iodides to electron-deficient alkenes

Cyanoborohydrides are efficient reagents in the reductive addition reactions of alkyl iodides and electron-deficient olefins. In contrast to using tin reagents, the reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine or carbon-chlorine bond. The reaction system was successfully applied to three-component reactions, including radical carbonylation. The rate constant for the hydrogen abstraction of a primary alkyl radical from tetrabutylammonium cyanoborohydride was estimated to be 4 M-1 s-1 at 25 °C by a kinetic competition method. This value is 3 orders of magnitude smaller than that of tributyltin hydride.

Stereospecific construction of chiral tertiary and quaternary carbon by nucleophilic cyclopropanation with bis(iodozincio)methane

The reaction of a ketone having a leaving group at the aposition, such as a,bepoxy ketone or asulfonyloxy ketone, with bis(iodozincio) methane affords a zinc alkoxide of cyclopropanol. The reaction proceeds by nucleophilic addition of the dizinc to the carbonyl group and a sequential intramolecular nucleophilic substitution of the introduced iodozinciomethyl group to the adjacent electrophilic carbon that has a leaving group. When an optically active a,β-epoxy ketone or asulfonyloxy ketone is treated with the dizinc, a zinc alkoxide of cyclopropanol having a chiral tertiary or quaternary carbon in the cyclopropane ring is obtained, and the obtained zinc alkoxide of cyclopropanol acts as a chiral ho-moenolate. When it is treated with an electrophile in the presence of copper cyanide, it gives an optically active a-tertiary or -quaternary ketone that retains high optical purity.

Tin-free giese reaction and the related radical carbonylation using Alkyl iodides and cyanoborohydrides

Tin-free Giese reaction and the related radical carbonylation process proceeded efficiently in the presence of sodium cyanoborohydride and tetrabutylammonium cyanoborohydride. The reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine and carbon-chlorine bonds. The iodine atom transfer followed by hydride reduction of the resulting carbon-iodine bond is proposed as a possible mechanism.

Preparation of zinc-homoenolate from α-sulfonyloxy ketone and bis(iodozincio)methane

Treatment of α-sulfonyloxy ketone with bis(iodozincio)-methane gives a zinc cyclopropoxide which is formed via a nucleophilic addition of the reagent to carbonyl group followed by an intramolecular substitution reaction. Copyright

Catalytic ketonisation over oxide catalysts. Part IX. Single step synthesis of aliphatic saturated and unsaturated C11 - C 13 ketones from carboxylic acids

Metameric undecan-x-ones (x = 2-6), dodecan-y-ones (y = 2-5), tridecan-z-ones (z = 4-7) and two unsaturated aliphatic ketones were prepared by vapor phase ketonisation of the appropriate monocarboxylic acids in the presence of 20 wt% MnO2/Al2O3 catalyst under flow conditions. The ketones were obtained in yields between 48 and 89% in a multigram scale (80-250 g). Their physical and spectral data have been determined.

Efficient ruthenium-catalyzed aerobic oxidation of alcohols using a biomimetic coupled catalytic system

Efficient aerobic oxidation of alcohols was developed via a biomimetic catalytic system. The principle for this aerobic oxidation is reminiscent of biological oxidation of alcohols via the respiratory chain and involves selective electron/proton transfer. A substrate-selective catalyst (ruthenium complex 1) dehydrogenates the alcohol, and the hydrogens abstracted are transferred to an electron-rich quinone (4b). The hydroquinone thus formed is continuously reoxidized by air with the aid of an oxygen-activating Co-salen type complex (6). Most alcohols are oxidized to ketones in high yield and selectivity within 1-2 h, and the catalytic system tolerates a wide range of O2 concentrations without being deactivated. Compared to other ruthenium-catalyzed aerobic oxidations this new catalytic system has high turnover frequency (TOF).

Catalytic activation of C-H and C-C bonds of allylamines via olefin isomerization by transition metal complexes

(matrix presented) The metal-catalyzed reaction of olefins with allylamines bearing coordination sites (2-pyridyl groups) was studied. With Ru3(CO)12 as catalyst, activation of C-H bonds led to the formation of ketimines that were hydrolyzed to give asymmetric ketones. With [(C8H14)2RhCl]2, both C-H and C-C bonds were activated and symmetric ketones were formed on hydrolysis. The reaction involves double bond migration of the allylamine to form an aldimine.