54844-65-4

Basic information

• Product Name: (Z)-6-HENICOSEN-11-ONE
• Synonyms: CIS-6-HENEICOSEN-11-ONE;Z-6-HENEICOSEN-11-ONE;(Z)-6-HENICOSEN-11-ONE;(z)-6-heneicosen-11-on;CIS-6-HENEICOSENE-11-ONE;(6Z)-6-Henicosen-11-one;(6Z)-Henicosane-6-ene-11-one;(Z)-6-Heneicosane-11-one
• CAS NO: 54844-65-4
• Molecular Formula: C₂₁H₄₀O
• Molecular Weight: 308.54
• Mol File: 54844-65-4.mol

Chemical Properties

• Boiling Point: 402.2°C at 760 mmHg
• Flash Point: 152.3°C
• Appearance: /
• Density: 0.843±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.12E-06mmHg at 25°C
• Refractive Index: 1.4564 (20℃)
• CAS DataBase Reference: (Z)-6-HENICOSEN-11-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-6-HENICOSEN-11-ONE(54844-65-4)
• EPA Substance Registry System: (Z)-6-HENICOSEN-11-ONE(54844-65-4)

Safety Data

• Hazardous Substances Data: 54844-65-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H40O/c1-3-5-7-9-11-13-15-17-19-21(22)20-18-16-14-12-10-8-6-4-2/h11,13H,3-10,12,14-20H2,1-2H3/b13-11-

Upstream product

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• 872-05-9 1-Decene 
• 143-33-9 sodium cyanide 
• 118506-57-3 (Z)-4-decen-1-magnesium chloride 
• 54844-71-2 (Z)-heneicos-6-en-11-ol 
• 17746-05-3 undecanoyl chloride 
• 71612-10-7 deca-1,4c-diene 
• 7766-48-5 1-iodo-4-pentene 

Relevant articles and documents

Synthesis of cis-12-Nonadecen-9-one, cis-13-Icosen-10-one, the Pheromone of Peach Fruit Moth, and cis-15-Henicosen-11-one, the Pheromone of Douglas Fir Tussock Moth

A convenient synthesis of cis-12-nonadecen-9-one (4a), cis-13-icosen-10-one (4b), the feromone of peach fruit moth, and cis-15-henicosen-11-one (4c), the pheromone of Douglas fit tussock moth, is described. 4a was synthesized from methyl 3-oxoundecanoate and 1-bromo-2-nonyne (2a) via 12-nonadecyn-9-one.The higher homolog 4b could be obtained from methyl-3-oxododecanoate and 2a.Similarly, 4c was prepared from methyl 3-oxotridecanoate and 1-bromo-3-nonyne (2b).

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.

Grignard-triggered fragmentation of vinylogous acyl triflates: Synthesis of (Z)-6-heneicosen-11-one, the Douglas fir tussock moth sex pheromone

Grignard reagents react with vinylogous acyl triflates in toluene via an addition-fragmentation sequence to afford alkynyl ketones. A streamlined synthesis of (Z)-6-heneicosen-11-one, the sex pheromone of the Douglas fir tussock moth, illustrates the utility of this method. Georg Thieme Verlag Stuttgart.

Sex pheromone and related compounds in the Ishigaki and Okinawa strains of the tussock moth Orgyia postica (Walker) (Lepidoptera: Lymantriidae)

Two distinct electroantennographycally active (EAG-active) components, A and B, and a weakly active component C were found in a solvent extract from virgin females of the Ishigaki strain of the tussock moth, Orgyia postica (Walker). Components A, B, and C were found in the extract of the females at 4.0, 0.5, and 4.0 ng/female respectively. Components A, B, and C were identified as (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene [(11S,12S)-1: posticlure], (6Z)-henicos-6-en-11-one (2), and (6Z,9Z)-henicosa-6,9-diene (3), respectively. Component B was absent in the extract from the Okinawa strain, in which components A and C were present at 2.0 and 1.5 ng/female respectively. (11S,12S)-1 and the racemic mixture showed attractiveness for both the Okinawa and Ishigaki strains, whereas (11R,12R)-1 did not. The addition of 2 significantly reduced the trap catches with (11S,12S)-1 on the Okinawa strain which lacked 2, while there was no significant inhibitory effect on the Ishigaki strain. The addition of 3 to (11S,12S)-1 did not significantly affect trap catches at Ishigaki or Okinawa. This confirmed that the attractant pheromone of O. postica of the Ishigaki strain is also (11S,12S)-1.

Synthesis of the four components of the female sex pheromone of the painted apple moth, Teia anartoides.

Four pheromone components of the female painted apple moth (Teia anartoides), an Australian insect pest, were synthesized. These were (Z)-6-henicosen-11-one (1), (6Z, 8E)-6,8-henicosadien-11-one (2), (Z)-cis-9,10-epoxy-6-henicosene (3), and (Z)-cis-9,10-epoxy-6-icosene (4). 2-Dodecanone was converted to 1 and 2, and both the enantiomers of 3 and 4 were synthesized from the enantiomers of 4-tert-butyldimethylsilyloxy-cis-2,3-epoxy-1-butanol.

Multicomponent reactions involving 2-methyleneaziridines: Rapid synthesis of 1,3-disubstituted propanones

Ring opening of 1-alkyl-2-methyleneaziridines 1 or 2 is accomplished with organocopper reagents (R2CuLi or RMgX/CuI) in the presence of boron trifluoride diethyl etherate giving 1-substituted propan-2-ones 3-9 in 42-88% yield. Ring opening with RMgC1/CuI in the absence of the Lewis acid allows further alkylation of the metalloenamine (metalated imine) intermediate in a regiocontrolled manner. The sequential formation of two new intermolecular carbon-carbon bonds in this reaction provides a rapid entry into a variety of 1,3-disubstituted propan-2-ones, including 11 and 14-23. The scope and mechanism of this multicomponent reaction (MCR) has been assessed. It is established that this MCR tolerates alkyl, aryl, and benzyiic Grignard reagents and a wide range of electrophiles, including alkyl iodides, bromides, and tosylates, as well as epoxides and aldehydes. In addition, gem-dimethyl substitution on the exocyclic double bond of the 2-methyleneaziridine is tolerated. This MCR has been applied to the one-pot synthesis of (Z)-6-heneicosen11-one, 25, an important sex attractant of the Tussock moth. Using 3-deuterio-1-(1-phenylethyl)2-methyleneaziridine, 26, we determined that this MCR occurs predominantly by direct ring opening at the sp3-hybridized aziridine carbon atom (C-3).

Synthesis of (Z)-6-heneicosen-11-one, (+/-)(Z)-14-methyl-8-hexadecen-1-ol and (+/-)-5,6-dehydrosenedigitalene

Three naturally occurring compounds (Z)-6-heneicosen-11-one (1), (+/-)-(Z)-14-methyl-8-hexadecen-1-ol (2) and (+/-)-5,6-dehydrosenedigitalene (3) have been synthesised using lithium tetrachlorocuperate catalysed coupling reaction.

Synthesis via ultrasound: A very short and convenient synthesis of (Z) and (E)-heneicos-6-en-11-ones

(Z)-Heneicos-6-en-11-one (1) and its E-isomer (2), the sex pheromones of Douglas fir tussock moth, have been synthesised utilising ultrasonic waves.

SYNTHESIS OF (Z)-HENICOSEN-11-ONE - A COMPONENT OF THE SEX PHEROMONES OF INSECTS OF THE Orgya FAMILY (ORGYIDAE)

The synthesis of (Z)-6-henicosen-11-one - a component of the sex pheromones of insects of the orgya family (Orgyidae) -from furfural is described.