40642-40-8

Basic information

• Product Name: Z-8-DODECEN-1-OL
• Synonyms: (8z)-8-dodecen-1-o;(8Z)-8-Dodecen-1-ol;8-Dodecen-1-ol, (Z)-;Z-8-DODECEN-1-OL;CIS-8-DODECEN-1-OL;(Z)-dodec-8-enol;cis-8-Dodecenol;8-Dodecen-1-ol, (8Z)-
• CAS NO: 40642-40-8
• Molecular Formula: C₁₂H₂₄O
• Molecular Weight: 184.32
• EINECS: 255-019-9
• Product Categories: insect pheromone
• Mol File: 40642-40-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 260.4±9.0℃ (760 Torr)
• Flash Point: 93.0±15.0℃
• Appearance: /
• Density: 0.846±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.00178mmHg at 25°C
• Refractive Index: 1.456
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 15.19±0.10(Predicted)
• CAS DataBase Reference: Z-8-DODECEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: Z-8-DODECEN-1-OL(40642-40-8)
• EPA Substance Registry System: Z-8-DODECEN-1-OL(40642-40-8)

Safety Data

• Hazardous Substances Data: 40642-40-8(Hazardous Substances Data)

Usage

Uses

(8Z)-8-Dodecen-1-ol is a component of various insect sex pheromones.

InChI:InChI=1/C12H24O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h4-5,13H,2-3,6-12H2,1H3/b5-4-

Upstream product

• 41589-71-3 8-Dodecyn-1-ol 
• 124731-26-6 methyl dodec-8Z-enoate 
• 65734-62-5 8-hydroxy-octyl-triphenyl-phosphonium bromide 
• 123-72-8 butyraldehyde 
• 105866-16-8 Phenylsulfonyl-8 dodecene-8E ol-1 acetate 
• 52957-00-3 (Z)-8-dodecenoic acid 
• 627-19-0 1-Pentyne 
• 821-57-8 7-chloroheptanoic acid 
• 18545-07-8 8-Dodecinsaeure 
• 4117-09-3 7-bromo-hept-1-ene 
• 18643-50-0 1-pentynyl lithium 
• 197901-17-0 Dodec-1-en-8-yne 
• 50816-19-8 8-bromooctanol 
• 5202-25-5 cyclododeca-5c,9t-diene-1r,2c-diol 

Downstream Products

• 28079-04-1 (Z)-8-dodecen-1-yl acetate 

Relevant articles and documents

Simple synthesis method for sex pheromones of oriental fruit moths

The invention belongs to the field of chemical synthesis, and particularly relates to a simple synthesis method for sex pheromones of oriental fruit moths. The method includes subjecting 1,8-octandiolas a raw material to unilateral bromination reaction to obtain 8-bromooctanol, reacting the 8-bromooctanol with triphenylphosphine to obtain 8-hydroxyoctyl triphenylphosphonium salt, subjecting the 8-hydroxyoctyl triphenylphosphonium salt and n-butanal to Wittig reaction under the action of an alkali to obtain (Z/E)-8-dodecene-1-alcohol, and performing acetylation under the action of pyridine andacetic anhydride to obtain a target product. The cis-trans ratio of enol obtained after the Wittig reaction ranges from 91.8:8.2 to 92.9:7.1; within the optimal attraction range, and by strictly controlling the amount of the acetic anhydride, the properly proportioned sex pheromones of the oriental fruit moths can be obtained according to a 'one-pot' method.

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.

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.

Copper-catalyzed cross-coupling of (Z)-allyl phenyl ethers with Grignard compounds in the synthesis of insect pheromones

(8Z)-Dodec-8-en-1-yl acetate (pheromone of oriental fruit moth Grapholita molesta) and (9Z)-dodec-9-en-1-yl acetate (pheromone of grape berry moth Paralobesia viteana) containing impurities of isomeric structures were synthesized via copper-catalyzed cross-coupling of (Z)-1-phenoxyhex-2-ene and (Z)-1-phenoxypent-2-ene, respectively, with Grignard compounds in the key stage.

Use of enyne compounds in the synthesis of insect pheromones

A new approach has been developed to the synthesis of monogenic insect pheromones with acetogenin and macrolide structures, using the low reactivity of ozone and of 9-borabicyclo[3.3.1]nonane towards an acetylenic function as compared with a vinyl function.

PHEROMONES OF INSECTS AND THEIR ANALOGS. XXI. SYNTHESIS OF ALK-8Z-EN-1-OLS AND THEIR ACETATES FROM A FUNCTIONALLY DIFFERENTIATED PRODUCT OF OZONOLYSIS OF CYCLOOCTENE

Dodec-8Z-en-1-ol (VIII) and tetradec-8Z-en-1-ol (IX) and the corresponding acetates (X and IX) - components of the sex pheromones of many species of Lepidoptera - have been synthesized from cyclooctene (I) in three stages.The ozonolysis of (I) ( -70 deg C, CH2Cl2-MeOH), NaHCO3; -20 deg C, Ac2O/Et3N) led to methyl 8-oxooctanoate (II).The DNPH of (II), (III), mp 59-61 deg C.The coupling of (II) with n-C3H17CH=PPh3 (IV) or with n-C5H11CH=PPh3 (V) (-70 deg C , 2h; 25 deg C, 15h, Ar) gave the methyl esters of dodec-8Z-enoic (VI) and tetradec-8Z-enoic (VII) acids, respectively.The reduction of (VI) and (VII) gave the corresponding alcohols (VIII) and (IX) by the acetylation (Ac2O-Py, 25 deg C, 24h) of which, (X) and (XI) , were obtained.The yields (percent): (II) 80, (VI) 45, (VII) 60, (VIII) 95, (IX) 90, (X) 75, (XI) 74.The IR and PMR spectra of compounds (II) and (VI-XI) are given.

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).

INSECT PHEROMONES AND THEIR ANALOGS. XIII. SYNTHESIS OF DODEC-8E-ENYL AND DODEC-8Z-ENYL ACETATES - COMPONENTS OF THE SEX PHEROMONES OF Grapholitha funebrana AND Grapholitha molesta

A new route is proposed for the synthesis of dodec-8E-enyl and dodec-8Z-enyl acetates which is based on the reaction of the Grignard reagent from the readily accessible 1-bromo-5-(1-ethoxyethoxy)pentane with 1-bromohept-3-yne - the bromide obtained from product of the β-hydroxyethylation of pent-1-yne with 2-chloroethylvinyl ether, hept-3-yn-1-ol, by a double decomposition reaction of its tosylate with lithium bromide.The key synthon - dodec-8-yn-1-ol - was converted with the aid of sodium in liquid ammonia into the stereochemical individual dodec-8E-enol, while its reduction with the aid of 9-borabicyclononane (BBN) gave the stereoisomeric alcohol exclusively with the Z configuration, as followed from the results of capillary GLC and the IR spectra of the corresponding acetates.The PMR spectra of the compounds synthesized are also given.

The Synthesis of (Z)-8-Dodecen-1-ol and its Acetate, Pheromone Components of the Oriental Fruit Moth (Grapholita molesta)

The two main sex pheromone components of the Oriental fruit moth (Grapholita molesta), viz. (Z)-8-dodecen-1-ol and its acetate, have been synthesized from (Z,E,E)-1,5,9-cyclododecatriene in approximately 15 percent overall yield.

ω-HYDROXYALKYL-PHOSPHONIUM SALTS AS "INSTANT-YLID" COMPONENTS: EXTREMELY CONVENIENT AND HIGHLY CIS-SELECTIVE SYNTHESIS OF ALKENOL-TYPE PHEROMONES

In less than 2 hours, (Z)-alkenols of 97-98percent stereoisomeric purity may be prepared and isolated (!) if a new type of "instant-ylids" is used.