14959-86-5

Basic information

• Product Name: CIS-7-DODECENYL ACETATE
• Synonyms: Z-7-DDA;Z-7-DODECEN-1-YL ACETATE;(7Z)-7-Dodecenyl acetate;(Z)-1-Acetoxy-7-dodecene;(Z)-7-Dodecen-1-ol acetate;(z)-7-dodecen-1-olacetate;(z)-7-dodecenylacetate;7-Dodecen-1-ol, acetate, (Z)-
• CAS NO: 14959-86-5
• Molecular Formula: C₁₄H₂₆O₂
• Molecular Weight: 226.36
• EINECS: 239-031-1
• Product Categories: insect pheromone
• Mol File: 14959-86-5.mol

Chemical Properties

• Melting Point: -22.4°C (estimate)
• Boiling Point: 300.1±21.0℃ (760 Torr)
• Flash Point: 61 °C
• Appearance: /
• Density: 0.881±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.00114mmHg at 25°C
• Refractive Index: 1.4485 (20℃)
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: CIS-7-DODECENYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-7-DODECENYL ACETATE(14959-86-5)
• EPA Substance Registry System: CIS-7-DODECENYL ACETATE(14959-86-5)

Safety Data

• RTECS: JR5265000
• Hazardous Substances Data: 14959-86-5(Hazardous Substances Data)

Usage

Uses

Used in Insect Attraction:
CIS-7-DODECENYL ACETATE is used as an insect attractant for the cabbage looper Trichoplusia. It serves as a sex pheromone, attracting male insects to female insects, which is essential for their mating process. This application is particularly useful in pest control and monitoring the population of these insects in agricultural settings.
Used in Pheromone Research:
CIS-7-DODECENYL ACETATE is used as a research tool in the field of pheromone studies. It helps scientists understand the chemical communication between insects, particularly in the context of mating and reproduction. This knowledge can be applied to develop more effective pest control strategies and improve our understanding of insect behavior.
Used in Chemical Synthesis:
CIS-7-DODECENYL ACETATE is used as a key intermediate in the synthesis of various chemical compounds. Its unique structure and properties make it a valuable building block for the development of new molecules with potential applications in various industries, such as pharmaceuticals, agriculture, and materials science.
Used in Insect Control:
CIS-7-DODECENYL ACETATE is used as a component in insect control strategies, particularly for the cabbage looper Trichoplusia. By mimicking the natural sex pheromone of the insect, it can be used to lure and trap male insects, disrupting their mating process and reducing their population. This approach is considered more environmentally friendly and targeted compared to traditional insecticides.
Used in Ecological Studies:
CIS-7-DODECENYL ACETATE is used in ecological studies to monitor and understand the behavior and population dynamics of the cabbage looper Trichoplusia and other related insects. This information can be valuable for developing sustainable pest management practices and preserving the balance of ecosystems.

InChI:InChI=1/C14H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h6-7H,3-5,8-13H2,1-2H3/b7-6-

Upstream product

• 16504-87-3 Dodec-7-in-1-yl acetat 
• 20056-78-4 Δ⁷-dodecen-1-ol 
• 75-36-5 acetyl chloride 
• 592-41-6 1-hexene 
• 5048-35-1 oct-7-en-1-yl acetate 
• 108-24-7 acetic anhydride 
• 20056-92-2 (Z)-7-dodecenol 
• 28254-05-9 (Z)-1-Acetoxy-7-dodecene Oxide 
• 98369-17-6 (7Z)-1-(tetrahydropyran-2'-yloxy)-7-dodecene 
• 42513-36-0 1-chloro-7-dodecyne 
• 69775-80-0 6-t-butyloxy-1-hexyl bromide 
• 112983-48-9 12-tert-Butoxy-dodecane-5,6-dione 
• 112983-43-4 1-tert-Butoxy-8-hydroxydodecan-7-on 
• 693-02-7 hex-1-yne 

Downstream Products

• 20056-92-2 (Z)-7-dodecenol 
• 2462-84-2 methyl (9E)-octadec-9-enoate 
• 19689-19-1 5-decene 
• 72025-18-4 myristelaidic acid methyl ester 
• 16695-41-3 (E)-7-dodecenyl acetate 
• 4084-07-5 1-tetradecene 

Relevant articles and documents

SILICON IN ORGANIC SYNTHESIS. STREREOSELECTIVE SYNTHESIS OF SOME INSECT SEX PHEROMONES

Trialkylsilallyl anion is alkylated by alkyl halides to give regio- and strereo-selectively the γ-product with trans-strereochemistry at double bond.The trans-vinylsilanes are transformed strereoselectively to Z-vinyl iodides.Coupling of the vinyl idiodes with organometallic reagents gives Z-alkenes.This approach has been applied to the synthesis of several insect sex pheromones.

Vinylic Organoboranes. 3. Pheromones via Organoboranes. 1. Stereospecific Synthesis of Straight-Chain Z-Monoolefinic Insect Pheromones via Lithium (1-Alkynyl)trialkylborates

Various insect pheromones with straight-chain Z-monoolefinic structures have been prepared from lithium (1-alkynyl)trialkylborates.Treatment of lithium (1-alkynyl)trialkylborates, readily prepared from lithium acetylides and trialkylboranes, with iodine under mild conditions produces the corresponding alkynes in essentially quantitative yield.Monohydroboration of the resultant alkyne with 9-borabicyclononane yields the corresponding (Z)-olefin after protonolysis.The combination of these two reaction sequences provides a general route for the synthesis of (Z)-olefins.The position of the double bond and the carbon-chain length are easily controlled by properly choosing the initial reactants.The incorporation of functional groups is also easily achieved because of the mild reaction conditions and the tolerance of hydroboration to many functional groups.High yield and purity of the products are obtained.

New synthesis of (Z)-5- and (Z)-7-monoene components of insect sex pheromones of the Lepidoptera order

A new procedure was developed for the synthesis of (Z)-5- and (Z)-7-monoene components of sex pheromones of Lepidoptera insects based on cometathesis of readily accessible cycloocta-1,5-diene and ethylene.

A Facile Synthesis of the Sex Pheromone of the Cabbage Looper Trichoplusia ni

The sex pheromone of the cabbage looper Trichoplusia ni Hubner, (Z)-7-dodecen-1-yl acetate, was synthesized via a bimolecular nucleophilic substitution reaction between the Grignard reagent of the protected bromohydrin with (Z)-2-hepten-1-yl acetate in the presence of CuI catalyst as a key step. An efficient synthetic method of preparation of the pheromone was achieved from (Z)-2-butene-1,4-diol in four steps with an overall yield of 22.1%.

Pheromone Synthesis via Organoboranes: A Stereospecific Synthesis of (Z)-7-Alken-1-ols

Traetment of trans-1-alkenylborepanes, obtained via monohydroboration of 1-alkynes with borepane, with iodine in the presence of a base results in the migration of one end of the cycloalkyl chain from boron to the adjacent carbon, producing intermediates containing the eight-membered borocane moiety, which undergoes a rapid deiodoboronation to afford the (Z)-7-alkenyl-1-boronate esters.These boronate esters on oxidation produce (Z)-7-alken-1-ols, providing a general, one-pot, and stereospecific synthesis of (Z)-7-alken-1-ols.

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.

Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**

The first continuous flow Z-selective olefin metathesis process is reported. Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. The designed continuous process permits various self-, cross- and macro-ring-closing-metathesis reactions, delivering products in high selectivity and short residence times. This technique is exemplified by direct application to the preparation of a range of pheromones and macrocyclic odorant molecules and culminates in a telescoped Z-selective cross-metathesis/ Dieckmann cyclisation sequence to access (Z)-Civetone, incorporating a serial array of continually stirred tank reactors.

Synthesis of (Z)-7-dodecylene-1-alcohol and acetic ester thereof

The invention belongs to the technical field of insect pheromone synthesis, and discloses a novel method for synthesizing (Z)-7-dodecylene-1-alcohol and acetic ester thereof. The method comprises thefollowing steps: taking n-valeraldehyde as a starting material and reacting with a Wittig reagent to obtain (Z)-7-dodecenoic acid ethyl ester; then performing reduction with lithium aluminum hydroxideto obtain (Z)-dodeca-carbon-7-alkene-1-alcohol; finally taking (Z)-dodeca-carbon-7-alkene-1-alcohol to react with acetyl chloride to obtain (Z)-7-dodecylene-1-farnesyl acetate. By adopting the method, Z-shaped double bonds are directly constructed through a coupling reaction of the Wittig reagent carrying an ester group at the tail end with aldehyde. The method is simple in synthesis route, and is environmentally friendly.

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.

Synthesis of sub-units of marine polycyclic ethers by ring-closing metathesis and hydroboration of enol ethers

A novel syntheses of Z-5-dezenol, Z-5-decenyl acetate, Z-7-dodecenol, Z- 7-dodecenyl acetate, Z-9-tricosene, Z-7,8-epoxy-methyloctadecane which are sex pheromone components of Lepidoptera and Diptera orders, have been realized via stereoselective cometathesis of 1,5-cyclooctadiene with ethylene in the presence of MoCls/SiO2-SnMe4 as a key reaction. The male cometathesis product, 1,Z-5,9-decatriene, has been converted into pheromone components monocloned above by regioselective partial hydroboration or hydrozirconation with help of 9-BBN and Cp2ZrHCl, correspondingly. The protonolysis of the obtained zirconosene derivative gave 1,Z-5-decadiene. Hydroboration-oxidation or hydroboration-C2-homologation of the latter but to Z-5- or Z-7 monoene pheromone components. Hydroboration-iodination of terminal double bond in 1,Z-5,9-decatriene, and further cross-coupling of the obtained iodine derivative with convenient lithium cuprates resulted in Z-9- tricosene, the main sex pheromone component of House Fly (Musca Domestica), or in 2-methyl-Z-7-octadecene, the presence of Gypsy Moth (Lymantria Dispar) sex attractant.