20056-92-2

Basic information

• Product Name: CIS-7-DODECEN-1-OL
• Synonyms: (7Z)-7-Dodecen-1-ol;(z)-7-dodecen-1-o;(Z)-7-Dodecen-1-ol;(Z)-7-Dodecenyl alcohol;7-Dodecen-1-ol, (Z)-;Looplure inhibitor;looplureinhibitor;CIS-7-DODECEN-1-OL
• CAS NO: 20056-92-2
• Molecular Formula: C₁₂H₂₄O
• Molecular Weight: 184.32
• EINECS: 243-488-2
• Product Categories: insect pheromone
• Mol File: 20056-92-2.mol
• Article Data: 25

Chemical Properties

• Melting Point: 77.27°C (estimate)
• Boiling Point: 283.3°C (estimate)
• Flash Point: 61 °C
• Appearance: /
• Density: 0.8597 (estimate)
• Vapor Pressure: 0.000919mmHg at 25°C
• Refractive Index: 1.4531 (estimate)
• Storage Temp.: −20°C
• CAS DataBase Reference: CIS-7-DODECEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-7-DODECEN-1-OL(20056-92-2)
• EPA Substance Registry System: CIS-7-DODECEN-1-OL(20056-92-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: JR5255000
• Hazardous Substances Data: 20056-92-2(Hazardous Substances Data)

Usage

Uses

(7Z)-Dodecen-1-ol is a sex pheromone of the cabbage Looper Trichoplusia ni Hubner. Synthesized from threo-aleuritic acid involving a simplified Wittig reaction. It is an intermediate in the synthesis of (7Z)-Dodecenyl Acetate, which is synthezied via nucleophilic substitution reaction between the Grignard reagent of the protected bromohydrin with (Z)-2-hepten-1-yl acetate in the presence of CuI catalyst.

InChI:InChI=1/C12H24O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h5-6,13H,2-4,7-12H2,1H3/b6-5-

Upstream product

• 110-62-3 pentanal 
• 76771-95-4 7-hydroxy-heptyl-triphenyl-phosphonium bromide 
• 59499-28-4 (Z)-4-nonen-1-ol 
• 1501-27-5 Pentanedioic acid, monomethyl ester 
• 3990-05-4 ethyl 6-formylhexanoate 
• 1124-42-1 1-ethoxy-cycloheptene 
• 70680-13-6 ethyl (Z)-dodec-7-enoate 
• 65270-96-4 methyl (Z)-dodec-7-enoate 
• 52956-99-7 cis-9-tetradecanoic acid 
• 83540-70-9 (Z)-2-Hepten-1-yl acetate 
• 533-87-9 9,10,16-trihydroxyhexadecanoic acid 
• 82260-32-0 4-(Z)-nonenemagnesium bromide 
• 502-42-1 cycloheptanone 
• 21406-61-1 pentyltriphenylphosphonium bromide 

Downstream Products

• 63851-40-1 (Z)-7-dodecenal 
• 205523-92-8 1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-5-((Z)-tridec-8-enyl)-benzene 
• 62897-10-3 ardisinol II 
• 426820-02-2 1-(4-Methoxy-benzenesulfonyl)-2-((Z)-tridec-8-enyl)-4-trityl-piperazine 
• 426819-90-1 3-((Z)-Tridec-8-enyl)-1-trityl-piperazine 
• 72530-36-0 (Z)-7-Dodecen-1-ol tosylat 
• 14959-86-5 (Z)-7-dodecenyl acetate 

Relevant articles and documents

Synthesis of Z-alkenes from alkenylcatecholboranes through reaction with RMgX and I2 induced rearrangement

Addition of RMgX and BrMg(CH2)nMgBr reagents to alkenylcatecholborane followed by iodine induced rearrangement and oxidation provided Z-olefins and Z-olefinic alcohols in moderate to good yields. This procedure is advantageous over the previous methods of synthesis of Z-olefins from alkenylboranes since the alkyl groups which are not available through hydroborations can also be utilized.

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.

Simple syntheses of (Z)-7-dodecen-1-ol, (Z)-7-tetradecen-1-yl acetate, (Z)-9-tetradecenal and (Z)-9-hexadecen-1-yl acetate from aleuritic acid

Insect sex pheromones are used for monitoring and management of crop pests. Four compounds (Z)-7-dodecen-1-ol, (Z)-7-tetradecen-1-yl acetate, (Z)-9-tetradecenal and (Z)-9-hexadecen-1-yl acetate reported as components of some important agricultural insect pests have been synthesized from theo-aleuritic acid (9,10,16-trihydroxyhexadecanoic acid) involving simplified Wittig reactions with improved yield.

Structure-activity relationships in platelet-activating factor (PAF). 11-From PAF-antagonism to phospholipase A2 inhibition: Syntheses and structure-activity relationships in 1-arylsulfamido-2-alkylpiperazines

1-Benzoyl-2-alkyl piperazines are strong inhibitors of Group I and II secreted PLA2s. An improvement of their activity was obtained by replacing the amide function by a sulfamide and by introduction of electrodonor substituents on the para position of the benzenesulfonyl moiety. Neither the position on one of the carbon of the piperazine ring nor the absolute configuration of this carbon have an effect on the affinity for one or the other group of PLA2, but the lipophilicity remains for these series an essential parameter. In addition structure-activity relationships allow new hypothesis on interaction of these piperazine derivatives with the catalytic site of PLA2s.