16974-11-1

Usage

Uses

Used in Pharmaceutical Industry:
Z-9-DODECEN-1-YL ACETATE is used as a key intermediate in the synthesis of antitumor agents. It plays a crucial role in the development of compounds that target and inhibit the growth of cancer cells, particularly solid malignancies such as liver, breast, lung, pancreatic, colorectal, and ovarian cancers.
Used in Aromatics Industry:
Z-9-DODECEN-1-YL ACETATE is used as a building block in the synthesis of various isomers of Panaxytriol and Falcarinol (F101100). These compounds are known for their diverse applications, including their use in the fragrance and flavor industries.
Used in Aromatase Inhibitors Synthesis:
Z-9-DODECEN-1-YL ACETATE is used as a precursor in the synthesis of aromatase inhibitors. These inhibitors are essential in the treatment of hormone-sensitive cancers, primarily breast and ovarian cancers. By inhibiting the aromatase enzyme, these compounds help reduce the production of estrogen, a hormone that can promote the growth of certain types of cancer cells.

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 1433, 1980 DOI: 10.1016/S0040-4039(00)92738-2

InChI:InChI=1/C14H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h4-5H,3,6-13H2,1-2H3/b5-4-

Upstream product

• 29541-97-7 9-acetoxynonal 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 91856-11-0 Δ⁹-dodecen-1-ol 
• 108-24-7 acetic anhydride 
• 35148-18-6 (Z)-9-dodecenol 
• 925-90-6 ethylmagnesium bromide 
• 98752-55-7 (Z)-2-(8-phenylthiodec-9-enyloxy)tetrahydro-2H-pyran 
• 811-49-4 ethyllithium 
• 75415-20-2 8-iodooctyl acetate 
• 74-86-2 acetylene 
• 17643-36-6 9-decyn-1-ol 
• 17976-80-6 7-hydroxyheptanenitrile 
• 21676-03-9 (Z)-3-hexenyl iodide 
• 693-80-1 oleyl acetate 

Downstream Products

• 56219-03-5 (Z)-9-Dodecenal 
• 29541-97-7 9-acetoxynonal 

Relevant academic research and scientific papers

SYNTHESIS OF PHEROMONE DERIVATIVES VIA Z-SELECTIVE OLEFIN METATHESIS

Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

Method for synthesizing grassland spodoptera litura sex pheromone active ingredients

The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing grassland spodoptera litura sex pheromone active ingredients (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. The method comprises the steps: using bromo-alcohol as a starting raw material; and firstly generating hydroxyl phosphonium salt with triphenylphosphine, then respectively carrying out Wittig coupling reaction with propionaldehyde and valeraldehyde to generate Z-type enol, and finally carrying out acetylation reaction with acetic anhydride to prepare (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. According to the method, hydroxyl phosphonium salt is used for Wittig reaction, two steps of hydroxyl protection and deprotection are omitted, the synthetic route is simplified, and the method has the advantages of being environmentally friendly and the like.

PRODUCTION OF FATTY OLEFIN DERIVATIVES VIA OLEFIN METATHESIS

In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

Concise syntheses of insect pheromones using Z-Selective cross metathesis

Very short synthetic routes to nine cisolefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported (see scheme). These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.

SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES

The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.

Palatable solid pesticidal compositions of ethylene and vinyl acetate copolymer

The invention comprises compositions in solid form of ethylene/vinyl acetate copolymer with an effective amount of bioactive agent, a protein/carbohydrate-lipid source, 0 to 20% of an edible oil and optionally an attractant, dye, preservative, adversive agent and biomarker and the use, thereof, to control pests.

Exo- and Endohormones. XI. Synthesis of Monounsaturated Sex Pheromones of Lepitoptera via α-Dicetones

α-Dicetones (5), prepared starting either with cyanohydrines (1) or with N,N-diethyl oxamate (6), were converted via the dihydrazones 11 ito acetylenes (12).Replacement of the protecting group by the acatate group and partial stereoselective reduction of the triple bond led finally to the title conpounds.

SYNTHESES A L'AIDE DE SULFONES (XXXVII). SYNTHESE DE TROIS PHEROMONES A UNE DOUBLE LIAISON Z : Z, 8-DDA; Z, 9-DDA; Z, 9-TDA.

The title compounds Z,8-dodecen-1yl acetate, Z,9-dodecen-1yl acetate and Z,9-tetradecen-1yl-acetate have been synthesized in three efficient steps: the reaction mixture from metalated ω-hydroxy sulfones and appropriate aldehydes was quenched with acetic anhydride yielding a diastereoisomeric mixture of β-acetoxy sulfones.Convergent elimination with powdered sodium hydroxide led to the E vinylic sulfone.Stereospecific hydrogenolysis of the sulfonyl group was carried out with sodium dithionite leading to the unsaturated alcohol (> 99percent Z).

PEPARATION OF (Z) and (E)-9-DODECENYL ACETATES

The sexual pheromones (Z)-9-dodecenyl acetate (IXa) and (E)-9-dodecenyl acetate (IXb) were synthesized using facile preparation of the acetylenic precursor 9-decyn-1-ol (IV), from tetrahydrofurfuryl chloride (I).Hydroxyl groups of intermediates in the subseqent steps were protected by the ethoxyethyl group.

A General Approach to the Synthesis of Mono-olefinic Insect Sex Pheromones of Z- or E-Configuration

A series of insect sex pheromones and structually related olefins have been synthesized with high stereoisomeric purity by two sequential cross-coupling reactions.Starting with (Z)- or (E)-1-bromo-2-phenylthioethene, (1) and (2), and Grignard reagents in the presence of nickel or palladium catalysts, two types of compounds have been prepared: (i) 1,2-dialkylethenes and (ii) alkenyl acetates.In the synthesis of Z-isomers, the first step involves a cross-coupling reaction of compound (1) with the appropriate Grignard reagent in the presence of a catalytic amount of .The second cross-coupling reaction is performed on the intermediate (Z)-phenylthioalkenes using a different Grignard reagent in the presence of (dppe=Ph2PCH2CH2PPh2) as a catalyst.In the synthesis of E-isomers both steps are cross-coupling reactions of Grignard reagents in the presence of as a catalyst, the first step involving compound (2) and the second step involving the intermediate (E)-phenylthioalkenes obtained.The Grignard reagents used in the synthesis of the alkenyl acetates derive from protected ω-halohydrins.