78631-45-5

Usage

InChI:InChI=1/C8H16O/c1-4-5-6-8(9)7(2)3/h4,7-9H,1,5-6H2,2-3H3

Upstream product

• 26144-88-7 2-methyl-hept-6-en-3-one 
• 1344115-80-5 CH₂CH₂CHCH₂BO₂(CH₂)3 
• 78-84-2 isobutyraldehyde 
• 821-09-0 n-Pent-4-enyl alcohol 
• 2100-17-6 4-pentenal 
• 920-39-8 isopropylmagnesium bromide 
• 5911-08-0 chloro(cyclopropyl)methane 
• 5162-44-7 1-bromo-4-butene 
• 7103-09-5 4-but-1-enylmagnesium bromide 

Downstream Products

• 78631-46-6 3-(2,6-dichlorobenzyloxy)-2-methyl-6-heptene 
• 941598-59-0 (+/-)-N-benzyl-N'-(1-i-propyl-penten-4-yl)-sulfamide 
• 1394313-55-3 (Z)-7-methyl-1,1-diphenyloct-2-ene-1,6-diol 
• 1394313-53-1 (E)-7-methyl-1,1-diphenyloct-2-ene-1,6-diol 
• 1123684-71-8 4-methyl-N-(2-methylhept-6-en-3-yl)benzenesulfonamide 
• 1185059-84-0 2-methylhept-6-en-3-yl (N-p-toluenesulfonyl)carbamate 
• 1185059-86-2 (+/-)-2-methylhept-6-en-3-yl 4-nitrophenylsulfonylcarbamate 
• 497063-34-0 8-isopropyl-7,8-dihydro-6H-oxocin-3-one 
• 497063-23-7 1-(1-isopropylpent-4-en-1-yloxy)-3-(triphenyl-λ⁵-phosphoranylidene)propan-2-one 
• 171557-96-3 Toluene-4-sulfonic acid 1-isopropyl-pent-4-enyl ester 

Relevant academic research and scientific papers

Cobalt-Catalyzed Stereoselective Synthesis of 2,5- trans-THF Nitrile Derivatives as a Platform for Diversification: Development and Mechanistic Studies

A straightforward protocol integrating a sustainable approach for the synthesis of new 2,5-trans-THF nitrile derivatives enabling an easy diversification of its side chain scaffolds is described. The reaction tolerated different aromatic and alkyl substit

Iron-Catalyzed Synthesis of α-Dienyl Five- and Six-Membered N-Heterocycles

The iron-catalyzed synthesis of α-dienyl N-heterocycles is reported. The method is cost-effective, atom-economic, and led to a range of substituted α-dienyl heterocycles in moderate to good yields and diastereoselectivities. The α-dienyl piperidines are key synthetic intermediates as demonstrated by the preparation of a panel of α-polyenyl N-heterocycles.

Solanesol furan spice substitute and synthesis method thereof

The invention belongs to the technical field of organic chemistry and tobaccos, and particularly relates to a novel solanesol furan spice substitute and a synthesis method thereof. A synthesis route for finally obtaining solanesol furan spice substitute from easily available raw materials comprises five steps.

Boron carboxylate catalysis of homoallylboration

Boron tris(trifluoroacetate) is identified as the first effective catalyst for the homoallyl- and homocrotylboration of aldehydes by cyclopropylcarbinylboronates. NMR spectroscopic studies and theoretical calculations of key intermediates and transition states both suggest that a ligand-exchange mechanism, akin to our previously reported PhBCl 2-promoted homoallylations, is operative. Our experimental and theoretical results also suggest that the catalytic activity of boron tris(trifluoroacetate) might originate from more facile catalytic turnover of the trifluoroacetate ligands (in agreement with DFT calculations) or from a lower propensity for formation of off-pathway reservoir intermediates (as observed by 1H NMR). This work shows that carboxylates are viable catalytic ligands for homoallyl- and homocrotylations of carbonyl compounds and opens the door to the development of catalytic asymmetric versions of this transformation.

Iron-catalyzed intramolecular allylic C-H amination

A highly selective C-H amination reaction under iron catalysis has been developed. This novel system, which employs an inexpensive, nontoxic [Fe IIIPc] catalyst (typically used as an industrial ink additive), displays a strong preference for allylic C-H amination over aziridination and all other C-H bond types (i.e., allylic > benzylic > ethereal > 3° > 2° ? 1°). Moreover, in polyolefinic substrates, the site selectivity can be controlled by the electronic and steric character of the allylic C-H bond. Although this reaction is shown to proceed via a stepwise mechanism, the stereoretentive nature of C-H amination for 3° aliphatic C-H bonds suggests a very rapid radical rebound step.

Homoallylboration and homocrotylboration of aldehydes

A simple method for addition of homoallylic fragments to aldehydes is described. Cyclopropanated allylboration reagents react with aldehydes in the presence of PhBCl2 to give high yields of bishomoallyl alcohols. Cyclopropanated cis-and trans-crotyl reage

Cyclopropylmethyl- and cyclobutylmethyllithium by an arene-catalyzed lithiation. Stability and reactivity

The reaction of (chloromethyl)cyclopropane 5 and (bromomethyl)cyclobutane 8 with lithium and a substoichiometric amount of DTBB, in the presence of different carbonyl compounds as electrophiles, in THF at -78 °C leads, after hydrolysis, to the corresponding cycloalkyl alcohols 6 and 9, respectively. However, when the same starting materials are lithiated using naphthalene as catalyst in diethyl ether and at higher temperature (0 or 25 °C), and then react with the same electrophiles, the final hydrolysis yields the corresponding unsaturated alcohols 7 and 10, respectively.

Striking AcOH acceleration in direct intramolecular allylie amination reactions

An experiment was conducted to demonstrate that a strong accelerating effect occurs in direct intramolecular allylic amination when the reaction is conducted in AcOH rather than in CHCl or THF. A round bottom flask under air was charged with N-tosylcarbamate 3a-j, Pd(OAc)2, bis-sulfoxide ligand LL, phenylbenzoquinone and AcOH. The reaction was allowed to stir at 45°C for 24 h. The reaction mixture was hydrolysed and extracted with AcOEt. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Cyclisation of 3a was repeated in CH2Cl 2 and in AcOH by using stoichiometric amounts of Pd(OAc) without benzoquinone. Stoichiometric tests and computational DFT analysis of the palladium reoxidation step provide an overview of the structural and energetic role of acetic acid in increasing the efficacy of the entire catalytic cycle.

Easy selective generation of (lithiomethyl)cyclopropane or homoallyllithium by a chlorine-lithium exchange

The reaction of (chloromethyl)cyclopropane 5 with lithium and a catalytic amount of DTBB (5 mol %) in the presence of different carbonyl compounds [Et2CO, n-Pr2CO, (c-C3H5)2CO, (CH2)5CO, PhCOMe, t-BuCHO, i-PrCHO, PhCHO] as electrophiles in THF at -78 °C leads, after hydrolysis with water, to the corresponding cyclopropyl alcohols 6. However, when the same starting material is lithiated using naphthalene as the arene catalyst in ether at 0 °C and then reacts with the same series of electrophiles, the final hydrolysis with water yields the corresponding unsaturated alcohols 7.

Copper(II) carboxylate promoted intramolecular diamination of terminal alkenes: Improved reaction conditions and expanded substrate scope

The copper(II) carboxylate promoted diamination reaction has been improved by the use of the organic soluble copper(II) neodecanoate [Cu(ND)2]. Cu(ND)2 allowed the less-polar solvent dichloroethane (DCE) to be used, and as a consequence, decomposition of less-reactive substrates could be avoided. High diastereoselectivity was observed in the synthesis of 2,5-disubstituted pyrrolidines. Ureas, bis(anllines), and α-amido pyrroles derived from 2-allylaniline could also participate in the diamination reaction.