154170-44-2Relevant articles and documents
Structure, Chirality, and Field Testing of a Male-Produced Aggregation Pheromone of Asian Palm Weevil Rhynchophorus bilineatus (Montr.) (Coleoptera: Curculionidae)
Oehlschlager, A. Cameron,Prior, R. N. B.,Perez, Alice L.,Gries, Regine,Gries, Gerhard,et al.
, p. 1619 - 1630 (1995)
4-Methyl-5-nonanol is a male-produced aggregation pheromone of the Asian palm weevil, Rhynchophorus bilineatus (Montr.). The pheromone was identified by coupled gas chromatographic-electroantennographic detection (GC-EAD) and coupled GC-mass spectrometric (MS) analyses of male- and female-produced volatiles. Analyses by GC-EAD and GC-MS of weevil-produced and stereoselectivity synthesized isomers of 4-methyl-5-nonanol on a Cyclodex B column, which separated isomers with baseline resolution, revealed that only (4S,5S)-4-methyl-5-nonanol is EAD active and produced by the males. In field experiments in Papua New Guinea, (4S,5S)-4-methyl-5-nonanol and a racemic mixture of diastereoisomers of it enhanced attraction of male and female weevils to sugarcane-baited traps. (4S,5S)-4-Methyl-5-nonanol is also an aggregation pheromone of two other Asian palm weevils, R. ferrugineus (Oliv.) and R. vulneratus (Panz.). The stereoisomeric mixture of 4-methyl-5-nonanol is currently used to manage populations of R. bilineatus in Papua New Guinea.
Synthesis of β-Methyl Alcohols: Influence of Alkyl Chain Length on Diastereoselectivity and New Attractants of Rhynchophorus ferrugineus
Le, Van-Dung,Dang, Chi-Hien,Nguyen, Cong-Hao,Nguyen, Hong-Ung,Nguyen, Thanh-Danh
, p. 5882 - 5886 (2021/06/21)
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
-
Paragraph 0127-0129, (2020/07/14)
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).
A formal, one-pot β-chlorination of primary alcohols and its utilization in the transformation of terpene feedstock and the synthesis of a C 2-symmetrical terminal bis-epoxide
Swatschek, Joerg,Grothues, Lydia,Bauer, Jonathan O.,Strohmann, Carsten,Christmann, Mathias
, p. 976 - 983 (2014/03/21)
A one-pot transformation of alkan-1-ols into 2-chloroalkan-1-ols is described. As a practical application, terpene-derived primary alcohols were converted into semiochemicals such as olfactory lactones (aerangis lactone, whisky lactone, and cognac lactone) and pheromones (cruentol and ferrugineol). Using heptane-1,7-diol as a bifunctional substrate, the corresponding bis-epoxide was synthesized by bidirectional synthesis in good yield and high enantioselectivity.
