35900-26-6

Usage

Uses

4-Methyl-5-nonanone is a pheromone produced by male West Indian sugarcane borer (WISB).

Synthesis Reference(s)

Journal of the American Chemical Society, 114, p. 4422, 1992 DOI: 10.1021/ja00037a070Tetrahedron Letters, 35, p. 3065, 1994 DOI: 10.1016/S0040-4039(00)76829-8

InChI:InChI=1/C10H20O/c1-4-6-8-10(11)9(3)7-5-2/h9H,4-8H2,1-3H3/t9-/m1/s1

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 123-15-9 2-methylvaleraldehyde 
• 223558-81-4 5-acetoxy-4,5-epoxynonane 
• 917-54-4 methyllithium 
• 3473-24-3 4,6-dibromo-nonan-5-one 
• 15681-48-8 lithium dimethylcuprate 
• 542-69-8 1-iodo-butane 
• 78428-09-8 2-Methyl-pentanoic acid pyridin-2-yl ester 
• 502-56-7 nonanone-5 
• 77-78-1 dimethyl sulfate 
• 62183-32-8 (1-butyl-pent-1-enyloxy)-trimethyl-silane 
• 333-27-7 methyl trifluoromethanesulfonate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 

Downstream Products

• 154170-44-2 (+/-)-syn-4-Methyl-5-nonanol 
• 154170-44-2 (+/-)-anti-4-Methyl-5-nonanol 
• 154170-44-2 (+/-)-4-Methyl-5-nonanol 

Relevant academic research and scientific papers

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.

PROCESSES FOR PREPARING 4-METHYL-5-NONANONE AND 4-METHYL-5-NONANOL

The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3), the process comprising at least a step of subjecting pentanoic anhydride of the following formula (1) and a 2-pentyl nucleophilic reagent of the following general formula (2), in which M represents Li, MgZ1, or ZnZ1, wherein Z1 represents a halogen atom or a 2-pentyl group, to a nucleophilic substitution reaction to produce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (7), the process comprising at least steps of preparing 4-methyl-5-nonanone and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (7).

PROCESSES FOR PREPARING 4-METHYL-5-NONANONE AND 4-METHYL-5-NONANOL

The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3): the process comprising at least a step of subjecting 2-methylpentanoic anhydride of the following formula (1) and an n-butyl nucleophilic reagent of the following general formula (2) in which M represents Li, MgZ1, or ZnZ1, wherein Z1 represents a halogen atom or an n-butyl group, to a nucleophilic substitution. reaction Coproduce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (5), the process comprising at least steps of preparing 4-methyl-5-nonanone; and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (5).

C -Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts

A versatile, selective, and recyclable heterogeneous catalytic method for the methylation of C-H bonds in alcohols, ketones, and indoles with methanol under oxidant-free conditions using a Pt-loaded carbon (Pt/C) catalyst in the presence of NaOH is reported. This catalytic system is effective for various methylation reactions: (1) the β-methylation of primary alcohols, including aryl, aliphatic, and heterocyclic alcohols, (2) the α-methylation of ketones, and (3) the selective C3-methylation of indoles. The reactions are driven by a borrowing-hydrogen mechanism. The reaction begins with the dehydrogenation of the alcohol(s) to afford aldehydes, which subsequently undergo a condensation reaction with the nucleophile (aldehyde, ketone, or indole), followed by hydrogenation of the condensation product by Pt-H species to yield the desired product. In all of the methylation reactions explored in this study, the Pt/C catalyst exhibits a significantly higher turnover number than other previously reported homogeneous catalytic systems. Moreover, it is demonstrated that the high catalytic activity of Pt can be rationalized in terms of the adsorption energy of hydrogen on the metal surface, as revealed by density functional theory calculations on different metal surfaces.

Highly Regioselective Monoalkylation of Ketones via Manganese Enolates Prepared from Manganese Amides.

Ketones are regioselectively converted to Mn-enolates by treatment with Mn-amides such as Ph(Me)NMnCl in THF at 20 deg C.Mn-enolates can then be regioselectively monoalkylated in good yields.The formation of di or polyalkylated products is never observed ( 1percent).

A CONVENIENT METHOD FOR THE DIRECT PREPARATION OF KETONES FROM 2-(6-(2-METHOXYETHYL)PYRIDYL) CARBOXYLATES AND ALKYL IODIDES BY USE OF ZINC DUST AND A CATALYTIC AMOUNT OF NICKEL DICHLORIDE

Treatment of 2-(6-(2-methoxyethyl)pyridyl) carboxylates with alkyl iodides in the presence of zinc dust and a catalytic amount of NiCl2 in DMF at 50 deg C affords unsymmetrical ketones in good yields by a one-pot procedure.