70004-03-4

Basic information

• Product Name: 4-methylheptan-3-one
• Synonyms: 3-heptanone, 4-methyl-; 4-methyl-3-heptanone; 4-Methylheptan-3-one; (4S)-4-methylheptan-3-one
• CAS NO: 70004-03-4
• Molecular Formula: C₈H₁₆O
• Molecular Weight: 128.212
• Mol File: 70004-03-4.mol

Chemical Properties

• Boiling Point: 159.929°C at 760 mmHg
• Flash Point: 44.625°C
• Density: 0.811g/cm³
• Vapor Pressure: 2.444mmHg at 25°C
• Refractive Index: 1.409
• CAS DataBase Reference: 4-methylheptan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methylheptan-3-one(70004-03-4)
• EPA Substance Registry System: 4-methylheptan-3-one(70004-03-4)

Safety Data

• Hazardous Substances Data: 70004-03-4(Hazardous Substances Data)

Upstream product

• 14979-39-6 4-methyl-3-heptanol 
• 591-78-6 n-hexan-2-one 
• 27771-19-3 (E)-4-methylhept-4-en-3-one 
• 96-22-0 pentan-3-one 
• 107-08-4 1-iodo-propane 
• 1027895-96-0 N'-(1-ethyl-2-methyl-pentylidene)-N,N-dimethyl-hydrazine 
• 87777-45-5 (E)-4-methylhept-4-en-3-ol 
• 7664-93-9 sulfuric acid 
• 84065-11-2 2-propyl-pent-1-en-3-ol 
• 333-27-7 methyl trifluoromethanesulfonate 
• 16795-73-6 3-pentanone N,N-dimethylhydrazone 
• 2550-21-2 3-methyl-2-hexanone 
• 74-88-4 methyl iodide 
• 80-48-8 methyl p-toluene sulfonate 

Relevant articles and documents

Synthesis of β-Methyl Alcohols: Influence of Alkyl Chain Length on Diastereoselectivity and New Attractants of Rhynchophorus ferrugineus

The diastereoselectivity of adducts in the addition reaction via the Felkin-Anh model is affected significantly by the steric effect of bulky groups. However, the influence of steric alkyl chain length has not been studied for the diastereoselectivity. In this work, we present a new strategy for the racemic synthesis of β-methyl alcohols to obtain various diastereomer ratios using the Felkin-Anh model. The addition of alkyl Grignard reagents to α-methyl aldehydes afforded diastereomer ratios of threo/erythro ≈ 2:1, while the reduction in structurally related ketones using LiAlH4 afforded ratios of threo/erythro ≈ 1:1. The experimental data showed no effect of alkyl chain length on either side on the stereoselectivity of adducts. All synthesized analogues were evaluated for attractiveness to Rhynchophorus ferrugineus weevils in the field. Five novel derivatives, including two alcohols and three ketones, were found to attract weevils in the field trials. Among them, 3-methyldecan-4-one (5b) and 4-methyldecan-5-ol (11a) were found to be the most attractive to the insects.

Investigating: Saccharomyces cerevisiae alkene reductase OYE 3 by substrate profiling, X-ray crystallography and computational methods

Saccharomyces cerevisiae OYE 3 shares 80% sequence identity with the well-studied Saccharomyces pastorianus OYE 1; however, wild-type OYE 3 shows different stereoselectivities toward some alkene substrates. Site-saturation mutagenesis of Trp 116 in OYE 3 followed by substrate profiling showed that the mutations had relatively little effect, opposite to that observed previously for OYE 1. The X-ray crystal structures of unliganded and phenol-bound OYE 3 were solved to 1.8 and 1.9 ? resolution, respectively. Both structures were nearly identical to that of OYE 1, with only a single amino acid difference in the active site region (Ser 296 versus Phe 296, part of loop 6). Despite their essentially identical static X-ray structures, molecular dynamics (MD) simulations revealed that loop 6 conformations differed significantly in solution between OYE 3 and OYE 1. In OYE 3, loop 6 remained nearly as open as observed in the crystal structure; by contrast, loop 6 closed over the active site of OYE 1 by ca. 4 ?. Loop closure likely generates a greater number of active site protein contacts for substrate bound to OYE 1 as compared to OYE 3. These differences provide an explanation for the differing stereoselectivities of OYE 3 and OYE 1, despite their nearly identical X-ray crystal structures.

Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones

The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.

One-pot multi-enzymatic synthesis of the four stereoisomers of 4-methylheptan-3-ol

The use of pheromones in the integrated pest management of insects is currently considered a sustainable and environmentally benign alternative to hazardous insecticides. 4-Methylheptan-3-ol is an interesting example of an insect pheromone, because its stereoisomers are active towards different species. All four possible stereoisomers of this compound were prepared from 4-methylhept-4-en-3-one by a one-pot procedure in which the two stereogenic centres were created during two sequential reductions catalysed by an ene-reductase (ER) and an alcohol dehydrogenase (ADH), respectively.

Enantioselective cyclopropanation of carboxylic esters with alkyl magnesium bromides in the presence of titanium(IV) (4R,5R)-TADDOLates

The reaction of isopropyl 4-chlorobutyrate with 3 equiv of n-BuMgBr in the presence of 1 equiv of titanium(IV) (4R,5R)-TADDOLate in diethyl ether led to the formation of (1S,2S)-(3-chloropropyl)-2-ethylcyclopropanol in 55-70% yield and 55-65% ee. The reaction was performed in the presence of 20 mol % of the catalyst without significant loss in yield and enantioselectivity when solutions of the carboxylic ester and the Grignard reagent were added simultaneously at an equal rate to a refluxing solution of the titanium catalyst in ether. The cyclopropanation of isopropyl propionate under the same conditions gave (1S,2S)-1-ethyl-2-propylcyclopropanol in 50% yield and 65% ee. Its absolute configuration was determined by chemical correlation through acid-catalyzed isomerization to enantiomerically enriched (R)-(-)-4-methyl-3-heptanone, known as a minor component of the trail pheromone of ant Aphaenogaster albisetosus and enantiomer of the alarm pheromone of leaf-cutting ants Atta texana.

Total synthesis of hoiamide C

Chemical equations presented. Hoiamide C was synthesized in 16 steps with an overall yield of 1.8% starting from homoallylic alcohol 18, unambiguously confirming its structure.

ASYMMETRIC ALPHA FUNCTIONALIZATION AND ALPHA, ALPHA BISFUNCTIONALIZATION OF ALDEHYDES AND KETONES

The present invention relates, generally, to asymmetric α-functionalization and to asymmetric α,α-bisfunctionalization of ketones and aldehydes and, in particular, to chiral auxiliaries suitable for use in effecting such functionalizations and to methods

Synthesis and absolute configuration of (S)-(+)-chichimol ketone: the defensive secretion of walking stick Agathemera elegans

The first enantioselective synthesis of chichimol ketone (4-methyl-1-hepten-3-one) is described and the absolute configuration of the main semiochemical compound is determined as having an (S)-configuration. The synthesis features the use of a ruthenium c

Simple and efficient asymmetric α-alkylation and α,α- bisalkylation of acyclic ketones by using chiral N-amino cyclic carbamate hydrazones

(Chemical Equation Presented) Distinguishing left from right: In the title reactions, chiral N-amino cyclic carbamates (ACCs) substantially diminish the drawbacks associated with the use of chiral dialkyl hydrazines, yet provide excellent stereoselectivity and high yields. In addition, ACCs exhibit a unique directing effect that overrides the inherent selectivity of lithium diisopropylamide (LDA) and enables the asymmetric α,α-bisalkylation of ketones (see scheme).

New Simple Polymeric Supports with Hydrazone Linkers for Solid-Phase Synthesis of Ketones and Primary Amines

The preparation of new solid supports with hydrazine anchoring groups and their application to solid-phase synthesis of ketones and primary amines are described. The supports were used for immobilization of ketones, 4-tert-butylcyclohexanone, pentan-3-one, acetone, N-methylpiperidone, N-benzylpiperidone, and tropinone in the form of their hydrazones. The polymer-supported hydrazones were subjected to deprotonation/alkylation procedure (LDA/RX) once or twice. The resulting alkylated products were cleaved off the solid support on treatment with trifluoroacetic acid in tetrahydrofuran providing α-alkylated or α,α′-bisalkylated ketones or were subjected to reductive cleavage with borane in tetrahydrofuran to give β-alkylated or β,β′-bisalkylated primary amines.