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.
Determination of absolute configurations of β-or γ-methyl substituted secondary alcohols by NMR spectroscopy
Takahashi, Haruko,Iwashima, Makoto,Iguchi, Kazuo
, p. 333 - 336 (1999)
A new method has been developed for determining the absolute configurations of acyclic β- or γ-methyl substituted secondary alcohols using their 2NMA esters. The 1H-NMR spectra of (R)- and (S)-2NMA esters of model compounds were measured, and Δδ values (δ(R-ester) - δ(S-ester) for the corresponding protons were compared between syn and anti compounds. Threshold values important to judging the relative stereochemistry of the two chiral centers bearing methyl and hydroxy groups were obtained. The absolute configuration of the chiral bearing a secondary hydroxy group is easily determined based on the sign of Δδ values as in the MTPA method and thus in the present study it was also possible to clearly determine the absolute configuration of the chiral center bearing a methyl group.
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
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, (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 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
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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).
Continuous-flow synthetic 4 - methyl -5 - nonanol method
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Paragraph 0021-0059, (2019/07/08)
Continuous-flow synthesis of 4 - methyl - 5 - nonyl alcohol method, the synthetic method 2 - methyl pentanals deprotecting reagent is butyl magnesium halide as the starting material, the addition reaction of the continuous method, then hydrolyzed under acidic conditions, after purification, to obtain high-purity of 4 - methyl - 5 - nonanol. The process of the invention is simple, a yield as high as 93%, easy to realize industrial production, solved in the prior art 4 - methyl - 5 - nonyl alcohol synthesis process complex, the yield is low, and the cost is high and is not suitable for industrial production of many problems.
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.
Syntheses of aggregation pheromones of the palm weevils rhyncophorus vulneratus and rphoenicis and of (+)- trans-whiskey lactone
Yadav,Rao, C. Venkateshwar,Prasad,Khazim Al Ghamdi, Ahmad Al
, p. 3894 - 3898 (2012/01/06)
(3S,4S)-3-Methyloctan-4-ol, (4S,5S)-4-methylnonan-5-ol, and (+)-trans-whiskey lactone [(4S,5R)-5-butyl-4-methyldihydrofuran-2(3H)-one] were synthesized stereoselectively by using a radical cyclization reaction as a key step. All three molecules were synthesized from a common cyclic acetal intermediate. Georg Thieme Verlag Stuttgart. New York.
Quantitative GC analysis of secondary alcohol pheromones: Determination of release rate of red palm weevil, Rhynchophorus ferrugineus, pheromone from lures
Zada,Soroker,Harel,Nakache,Dunkelblum
, p. 2299 - 2306 (2007/10/03)
Aliphatic secondary alcohols are components of several aggregation pheromones of important beetle and weevil pests. Some of these pheromones are used frequently for the monitoring and mass trapping of the relevant insects. We encountered severe difficulties in direct GC quantitative analysis of these compounds. Therefore, we developed a simple GC analysis of secondary alcohols converting them to trifluoroacetyl derivatives and using secondary alcohol acetates as internal standards. This method was applied for the quantitative analysis of several secondary alcohols, including the aggregation pheromone components of the almond bark beetle and the red palm weevil. The release rate of the latter pheromone from commercial lures was also determined.
Asymmetric synthesis of phoenicol, ferrugineol and cruentol, aggregation pheromones of Rhynchophorus spp.
Odriozola, Jose M.,Garcia, Jesus M.,Gonzalez, Alberto,Gil, Pilar
, p. 4627 - 4632 (2007/10/03)
Syntheses of phoenicol, ferrugineol, and cruentol, aggregation pheromones of Rhynchophorus palm weevils, have been achieved with an overall yield of 42, 40 and 41%, respectively (five steps), in high enantiomeric purity. (C) 1999 Elsevier Science Ltd.
