Category: 50767-78-7

Sex pheromones of two noctuid moths was written by Nesbitt, Brenda F.;Beevor, P. S.;Cole, R. A.;Lester, R.;Poppi, R. G.. And the article was included in Nature (London), New Biology in 1973.Synthetic Route of C14H24O2 The following contents are mentioned in the article:

The attractant scent in Diparopsis castanea consisted of 1-dodecyl acetate (I), trans-9-decen-1-yl acetate (II), 11-dodecen-1-yl acetate (III), and trans-9,11-dodecadien-1-yl acetate (IV). Electroantennogram responses of the male moths were in the order: IV ≫ II > III ≫ I. In laboratory trap tests, only IV was slightly attractive at low loadings. The addition of 20-30% III greatly enhanced the attractiveness of IV. The female Spodoptera littoralis sex scent consisted of 1-tetradecyl acetate (V), cis-9-tetradecen-1-yl acetate (VI), trans-11-tetradecen-1-yl acetate (VII), and cis-9,trans-11-tetradecadien-1-yl acetate (VIII). Electroantennogram responses of the male moths were in the order: VIII > VI ≫ VII > V. In laboratory trap testing, the natural proportions of V, VI, VII, and VIII were attractive. Brushes of the male S. littoralis located near the abdominal tip contained VIII. S. littoralis females gave electroantennogram responses to V, VI, VII, and VIII. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Synthetic Route of C14H24O2).

(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Synthetic Route of C14H24O2

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New synthetic reactions utilizing organosilicon and tin compounds was written by Ochiai, Masahito. And the article was included in Yakugaku Kenkyu no Shinpo in 1986.Computed Properties of C14H24O2 The following contents are mentioned in the article:

Synthesis of functionalized olefins utilizing organosilicon and tin compounds are described. The silicon-directed thermal elimination from β-triethylsilyl sulfoxides followed by protodesilylation provides a new method to achieve the regiospecific introduction of a double bond. Thus, thermolysis of PhCH₂CH(CH₂SiMe₃)S(O)Ph, followed by protodesilylation, gave PhCH₂CH:CH₂. The desulfonation of vinyl sulfones via the β-elimination of β-tributylstannylorganosulfur compounds has been developed and the reaction was applied to the stereoselective synthesis of functionalized olefins, including 1,3-dienes, allenes, vinyl sulfides, vinylsilanes, vinylstannanes, and allylsilanes. Oxidative 1,4-fragmentation of γ-tributylstannyl alcs. using iodosylbenzene produces unsaturated carbonyl compounds; the fragmentation, combined with conjugate addition of tributylstannyllithium and reduction or alkylation, offers an efficient procedure for the reductive and alkylative ring opening of cyclic vinyl ketones. Medium size unsaturated lactones are synthesized by employing the fragmentation as a key step. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Computed Properties of C14H24O2).

(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Computed Properties of C14H24O2

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Ester – Wikipedia,
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Regional convergence in the reaction of heterosubstituted allylic carbanions via allylic aluminum and boron ate complexes was written by Yamamoto, Yoshinori;Yatagai, Hidetaka;Saito, Yoshikazu. And the article was included in Journal of Organic Chemistry in 1984.Electric Literature of C14H24O2 The following contents are mentioned in the article:

The regiochem. in reactions of heterosubstituted allylic carbanions (I) is highly controlled via allylic Al or B ate complexes which direct both carbonyl compounds and reactive halides to the α-position with high regioselectivity. For example, carbonyl compounds react with I [R = Me₂CHO (II), MeOCH₂O (III), Me₂CHS (IV), PhSe, Me₃Si] at the α-position via the ate complexes. Although the reactions of the ate complexes (V) with aldehydes generally produce a mixture of erythro and threo isomers, the Al ate complex of III gives the erythro isomer with very high stereoselectivity. This procedure is applied to the stereoselective synthesis of exo-brevicomin. With allylic halides, the II and IV substituted allylic carbanions again react at the α-position via the ate complexes. However, the coupling mode is entirely different; the α-α’ coupling product is obtained from II, while the α-γ’ coupling product is produced from IV. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Electric Literature of C14H24O2).

(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Electric Literature of C14H24O2

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A stereospecific synthesis of 12-acetoxy-1,3-dodecadiene, the sex pheromone of Diparopsis castanea (Hampson) was written by Cardillo, Giuliana;Orena, Mario;Porzi, Gianni;Sandri, Sergio. And the article was included in Gazzetta Chimica Italiana in 1980.COA of Formula: C14H24O2 The following contents are mentioned in the article:

(E)-CH₂:CHCH:CH(CH₂)₈OR (I; R = Ac), the pheromone of the red bollworm moth, was stereospecifically prepared by alkylation of THPOCH₂CCH (II, THP = tetrahydropyranyl) and successive LiAlH₄ reduction Thus, reaction of equimolar THPO(CH₂)₈I with II, BuLi, and (Me₂CH)₂NH in THF gave 80% R¹O(CH₂)₈CCCH₂OR¹ (III; R¹ = THP), which was hydrolyzed over Amberlyst H-15 in MeOH to give 92% diol (III; R¹ = H) (IV). Reduction of 20 mmol IV with LiAlH₄ gave 95% HO(CH₂)₈CH:CHR² (V; R² = CH₂OH), which (10 mmol) was oxidized with MnO₂ in CH₂Cl₂ to give quant. aldehyde (V; R² = CHO) (VI). Methylenation of 10 mmol VI with Hg, Mg, and CH₂I₂ in Et₂O at room temperature gave 83% I (R = H), which (5 mmol) was acetylated in pyridine at 0° to give 98% I (R = Ac). This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7COA of Formula: C14H24O2).

(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.COA of Formula: C14H24O2

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Female sex pheromone release and the timing of male flight in the red bollworm Diparopsis castanea Hmps. (Lepidoptera, Noctuidae), measured by pheromone traps was written by Marks, R. J.. And the article was included in Bulletin of Entomological Research in 1976.COA of Formula: C14H24O2 The following contents are mentioned in the article:

The female sex pheromone gland of D. castanea consists of modified intersegmental tissue between the 8th and 9th abdominal segments. Glands contain an average of 12.75 × 10-3 μg of pheromone consisting of 80.4% trans-9,11-dodecadien-1-yl acetate (range 72.7-86.7%) and 19.6% 11-dodecen-1-yl acetate (range 13.3-27.3%). Although no significant correlation exists between female body weight and pheromone content of the gland, the duration of sex pheromone release over the lifespan of a female is positively correlated with its weight on emergence. Six behavioral steps may be recognized in the precopulatory behavior of females, but the frequency and duration of sex pheromone release is strongly influenced by both temperature and light intensity. At 25° females typically call on ≥2 occasions for 41-50% of the night, calling commencing earlier at cool (13.4.degree.) temperatures than at moderate (19.4.degree.) or warm (25.0.degree.) temperatures Calling by mated females increases considerably from 4 to 5 nights after mating but is typically of shorter duration than for virgins. The dispersal flight of Diparopsis males in cotton crops commences almost immediately after sunset and before the end of dusk, with peak male catches in sex pheromone traps occurring earlier in the cooler months of May and June (20:00-2:00 hr) than in November (02:00-04:00 hr). The Diparopsis synthetic sex pheromone, dicastalure, traps a greater proportion of males and females both earlier and later in the night than virgin females and this timing advantage may be important in a pheromone control program based on disruption of communication between the sexes. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7COA of Formula: C14H24O2).

(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.COA of Formula: C14H24O2

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Sex pheromone of Eupoecilia ambiguella female: analysis and male response to ternary blend was written by Arn, Heinrich;Rauscher, Stefan;Buser, Hans Rudolf;Guerin, Patrick M.. And the article was included in Journal of Chemical Ecology in 1986.Computed Properties of C14H24O2 The following contents are mentioned in the article:

Sex gland extracts and washes of E. ambiguella contained 10-20 ng/female of the primary sex pheromone component Z-9-dodecenyl acetate (Z9-12:Ac), accompanied by a number of related compounds These are (E9-12:Ac), Z-9-dodecen-1-ol (Z9-12:OH), saturated acetates of 12, 16, 18, and 20 Cs, and traces of a doubly unsaturated acetate, tentatively identified as a 9,11-dodecadienyl acetate. Octadecyl acetate (18:Ac) predominated among the pheromone-related components, making up 1-2, occasionally 20-30-fold the amount of Z9-12:Ac. The same compounds were also found in field-collected females and in effluvia. Z-9-Undecenyl acetate, which is a male attractant on its own, was also found in a sample of female effluvia. A hierarchy in the ethol. function of the pheromone components was observed Z9-12:Ac was an attractant for E. ambiguella males. Dodecyl acetate (12:Ac) was not attractant on its own, but augmented male catch when added to the main attractant. Addition of 18:Ac augmented attraction only when both Z9-12:Ac and 12:Ac were present. Wind-tunnel tests demonstrated that 18:Ac also raised the disorientation threshold, as previously shown for 12:Ac. Other compounds, with the possible exception of addnl. saturated acetates, had either no effect on trap catch or, in the case of E9-12:Ac, Z9-12:OH, and E-9,11-dodecadienyl acetate, were inhibitory above a certain level. A blend of roughly equal parts of Z9-12:Ac, 12:Ac, and 18:Ac provided the best blend for E. ambiguella known to date. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Computed Properties of C14H24O2).

(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Computed Properties of C14H24O2

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Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthesis of 9(E)-dodecenyl acetate and 9(E),11-dodecadienyl acetate, female sex pheromones of red bollworm moth, Diparopsis castanea Hmps was written by Vig, O. P.;Sharma, M. L.;Verma, N. K.;Malik, Neera. And the article was included in Indian Journal of Chemistry in 1980.Name: (E)-Dodeca-9,11-dien-1-yl acetate The following contents are mentioned in the article:

Undec-10-en-1-ol reacted with dihydropyran in the presence of a catalytic amount of concentrate HCl at 0° to give the pyranyl ether, which on epoxidation with m-chloroperbenzoic acid gave the epoxide I in very high yields. Cleavage of I with lithium diisopropylamide under N₂ atm. gave 11-(tetrahydropyranyloxy)undec-2(E)-en-1-ol (II), which on oxidation by pyridinium chlorochromate in dry CH₂Cl₂ gave 11-(tetrahydropyranyloxy)undec-2(E)-en-1-al (III). III on Wittig reaction with methylenetriphenylphosphorane in Me₂SO under N₂ gave the conjugated diene IV, which was cleaved to give 9(E),11-dodecadien-1-ol. This with isopropenyl acetate gave 9(E),11-dodecadienyl acetate. Conversion of the intermediate alc. II into the corresponding mesylate with MeSO₂Cl/Et₃N in dry CH₂Cl₂ at 0° and subsequent treatment with lithium dimethylcuprate under N₂ atm. gave 12-(tetrahydropyranyloxy)dodec-3(E)-ene. Removal of the protective pyranyl group from the latter gave 9(E)-dodecen-1-ol, which with Ac₂O/dry pyridine gave 9(E)-dodecenyl acetate. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Name: (E)-Dodeca-9,11-dien-1-yl acetate).

(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Name: (E)-Dodeca-9,11-dien-1-yl acetate

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Ester – Wikipedia,
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Stereoselective synthesis of (E)-, (E,Z)- and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as the key step was written by Yamada, Sachiko;Ohsawa, Hideto;Suzuki, Takayoshi;Takayama, Hiroaki. And the article was included in Journal of Organic Chemistry in 1986.Computed Properties of C14H24O2 The following contents are mentioned in the article:

A new stereoselective method is presented for synthesizing (E)-, (E,Z)-, and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as the key step. Direct alkylation of 3-sulfolene I (R = H) (II) at the 2-position proceeds with good yields when labile sulfolene α-carbanion is generated in the presence of alkyl iodides in THF-HMPA solution at -78°. Alkylation of 2-alkyl-3-sulfolenes I (R = alkyl) give trans-2,5-dialkyl-3-sulfolenes III (R, R¹ = alkyl) with 100% regioselectivity and more than 90% stereoselectivity. Desulfonylation of III was examined and the conditions to give stereoselectively the corresponding (E,Z)- and (E,E)-conjugated dienes were found. Three insect pheromones, (E)-9,11-dodecadien-1-yl acetate, a sex pheromone of the red bollworm moth, (E,E)-8,10-dodecadien-1-ol, a sex pheromone of the codling moth, and (E,E)-11,13-hexadecadienal, a sex pheromone of the cabbage webworm, were synthesized by starting from II with nearly 100% stereoselectivity. Cyclohexenes IV (R = alkyl) were prepared from the corresponding I via a Diels-Alder reaction with maleic anhydride. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Computed Properties of C14H24O2).

(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Computed Properties of C14H24O2

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Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Mass spectra of lepidopterous sex pheromones with a conjugated diene system was written by Ando, Tetsu;Ogura, Yasushi;Uchiyama, Masaaki. And the article was included in Agricultural and Biological Chemistry in 1988.Name: (E)-Dodeca-9,11-dien-1-yl acetate The following contents are mentioned in the article:

Dodecadien-1-ols, tetradecadien-1-ols, and hexadecadien-1-ols with a conjugated (E,E)- or (E)-diene system between the ω1,ω3- and ω5,ω7-positions, their acetates, and aldehyde derivatives (lepidopterous sex pheromones and candidates) were analyzed by electron-impact mass spectrometry, which was operated at 70-eV ionization voltage. Three functional derivatives with a same diene system presented a similar spectral pattern, except for the mol. ions (M⁺), [M-H₂O]⁺ of the alcs., and [M-CH₃CO₂H]⁺ of the acetates. Each isomer showed a characteristic fragment ion series of C_nH_2n-2⁺ ∼C_nH_2n-5⁺ (C₄∼C₉), which reflected the double-bond position in the mol., indicating a method for determining the position of a natural diene pheromone by comparing its mass spectrum with those of the synthetic dienes. By this method, the natural pheromone of Hellula undalis was confirmed to be a ω3,ω5-diene. Furthermore, the fitness indexes proposed by Y. Kuwahara et al. (1986) were calculated for some pheromone components, using the mass spectra of synthetic dienes, to examine the possibilities and limitations for applications of those mass spectra to natural pheromone studies. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Name: (E)-Dodeca-9,11-dien-1-yl acetate).

(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Name: (E)-Dodeca-9,11-dien-1-yl acetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Laboratory evaluation of the sex pheromone and mating inhibitor of the red bollworm Diparopsis castanea Hampson (Lepidoptera, Noctuidae) was written by Marks, R. J.. And the article was included in Bulletin of Entomological Research in 1976.Computed Properties of C14H24O2 The following contents are mentioned in the article:

The four components of the sex pheromone of D. castanea are dodecan-1-yl acetate (I) [112-66-3], trans-9-dodecen-1-yl acetate (II) [35148-19-7], 11-dodecen-1-yl acetate (III) [35153-10-7], and trans-9,11-dodecadien-1-yl acetate (IV) [50767-78-7]. Increasing the proportion of II in a I/II/III/IV mixture progressively decreased male excitation; in the absence of I all concentrations of II tested were equally inhibitory. The synthetic combination of 80% IV (93% trans:7% cis) and 20% III (dicastalure), was 485-fold more potent in eliciting male activity than a female sex pheromone gland extract Reduction in male response to crude extract occurred through exposure of males to glandular II and through reduced pheromone volatility caused by extracted triglycerides. Maximum quantities of pheromone were detected in the female sex pheromone gland 6-12 h into scotophase and for ≥30 min into photophase. Greater bioassay responses were elicited by the optimal field combination of 80% IV and 20% III than for other ratios tested. Excitation and clasper extension were observed in response to the nonattractive III; this indicates a role in close-range mating behavior for this component. The threshold level of male response to sex pheromone occurred at an aerial concentration of 9.2 mols. IV/mm3/s. This suggests that aerial concentrations of 102-103 times the male threshold response level may be sufficient to cause successful communication disruption in the field. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Computed Properties of C14H24O2).

(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Computed Properties of C14H24O2

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics