24089-00-7

Usage

Safety Profile

Moderately toxic by ingestion. Low toxicity by skin contact. A severe skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C9H18O/c1-4-6-7-8-9(3,10)5-2/h5,10H,2,4,6-8H2,1,3H3

Upstream product

• 110-43-0 n-pentyl methyl ketone 
• 1826-67-1 vinyl magnesium bromide 
• 23580-51-0 3-methyl-1-octyn-3-ol 
• 1838-94-4 isoprene epoxide 
• 4312-99-6 oct-1-en-3-one 
• 917-54-4 methyllithium 
• 593-60-2 Vinyl bromide 

Downstream Products

• 66008-66-0 1-methyl-1-(n-pentyl)-2-propenyl acetate 

Relevant academic research and scientific papers

Prenyl Praxis: A Method for Direct Photocatalytic Defluoroprenylation

The prenyl fragment is the quintessential constituent of terpenoid natural products, a diverse family which contains numerous members with diverse biological properties. In contrast, fluorinated and multifluorinated arenes make up an important class of anthropogenic molecules which are highly relevant to material, agricultural, and pharmaceutical industries. While allylation chemistry is well developed, effective prenylation strategies have been less forthcoming. Herein, we describe the photocatalytic defluoroprenylation, a powerful method that provides access to "hybrid molecules" that possess both the functionality of a prenyl group and fluorinated arenes. This approach involves direct prenyl group transfer under very mild conditions, displays excellent functional group tolerance, and includes relatively short reaction times (4 h), which is the fastest photocatalytic C-F functionalization developed to date. Additionally, the strategy can be extended to include allyl and geranyl (10 carbon fragment) transfers. Another prominent finding is a reagent-dependent switch in regioselectivity of the major product from para to ortho C-F functionalization.

Oxidative rearrangement of tertiary allylic alcohols employing oxoammonium salts

(Chemical Equation Presented) Practical and highly efficient methods for oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated carbonyl compounds employing oxoammonium salts are described. The methods developed are applicable to acyclic substrates as well as medium membered ring substrates and macrocyclic substrates. The counteranion of the oxoammonium salt plays crucial roles on this oxidative rearrangement.

Enantio- and stereospecific syntheses of 15(R)-Me-PGD2, a potent and selective DP2-receptor agonist

(Chemical Equation Presented) The first total synthesis of 15(R)-Me-PGD2 3 is reported. The synthesis is based on the enantioselective and stereospecific syntheses of synthon 17 and its attachment to the five-membered ring by a olefin cross metathesis reaction. This approach permits the introduction of a side chain with a predetermined stereogenic center into the prostanoid ring, resulting in the synthesis of 15R-methyl prostaglandin D2 and allows rapid access to other prostanoids.

An efficient DABCO-catalyzed Ireland-Claisen rearrangement of allylic acrylates

A novel DABCO-catalyzed Ireland-Claisen [3,3]-rearrangement of allylic acrylates to give α-methylene-γ,δ-unsaturated carboxylic acids in the presence of an excess of TMSCl and DBU in refluxing acetonitrile was developed. The protocol provides an easy entry to α-methylene-γ, δ-unsaturated carboxylic acids from allylic alcohols in good yields. Georg Thieme Verlag Stuttgart.

Regioselective SN2 opening of vinylic epoxides with trialkylzincates and trialkylaluminates

The use of trialkylorganozincates and tetraalkylaluminates allows regioselective SN2 nucleophilic opening of vinylic epoxides. The reaction occurs with an anti-substitution pattern and can be applied to a wide range of substrates. We also show that the solvent and the structure of the epoxide have an influence on the substitution products' ratio. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

EFFECT OF THE STRUCTURE OF SUBSTITUTED PROPARGYL AND ALLYL ALCOHOLS ON THE RATE OF THEIR LIQUID PHASE HYDROGENATION ON A Pd-Ru ALLOY MEMBRANE CATALYST

The rates of hydrogenation of substituted propargyl and allyl alcohols in the liquid phase on a Pd-Ru alloy membrane catalyst are described by a two-parameter Taft equation which takes into account the inductive and steric effects of the substituents.The values of the parameters at 363 K with H2 at atmospheric pressure are: ρ* = -0.20, δ = 0.10 and ρ+ = -1.1, δ = 1.3 respectively.

8,12-Dialkyl-PGE, and PGF1α

Prostaglandins E1 -type and F1 -type compounds of the formula EQU1 wherein R is hydrogen or a hydrocarbyl group containing from 1 to 12 carbon atoms, inclusive, wherein W is EQU2 or O =, wherein R7, R8, R9, R10, R11, R12, R13, and R14 are hydrogen or alkyl of 1 to 4 carbon atoms, inclusive, provided (1) that at least one of R7, R8, R9, R10, R11, R12, R13, and R14 is alkyl (2) that when R13 is alkyl, at least one of R7, R8, R9, R10, R11, R12, and R14 is alkyl, and (3) that when R7 is alkyl or thwn R7 and R8 are alkyl, at least one of R9, R10, R11, R12, R13, and R14 is alkyl; and the enantiomers and racemic mixtures thereof. These are useful for the same pharmacological purposes as the unsubstituted prostaglandins.