42991-03-7

Basic information

• Product Name: Oxirane, 2-decyl-3-(5-methylhexyl)-, trans-
• Synonyms: trans-dispalure;trans-7,8-epoxy-2-methyloctadecane;rac-trans-Disparlure;(+/-)-trans-disparlure;(2S,3S)-2-Decyl-3-(5-methyl-hexyl)-oxirane;2-methyl-(E)-7,8-epoxyoctadecane;(E)-2-methyl-7,8-epoxyoctadecane
• CAS NO: 42991-03-7
• Molecular Formula: C19H38O
• Molecular Weight: 282.51
• Mol File: 42991-03-7.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: Oxirane, 2-decyl-3-(5-methylhexyl)-, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxirane, 2-decyl-3-(5-methylhexyl)-, trans-(42991-03-7)
• EPA Substance Registry System: Oxirane, 2-decyl-3-(5-methylhexyl)-, trans-(42991-03-7)

Safety Data

• Hazardous Substances Data: 42991-03-7(Hazardous Substances Data)

Upstream product

• 51050-50-1 trans-7,8-epoxy-2-methyloctadecane 
• 626-88-0 1-bromo-5-methylpentane 
• 90359-67-4 (E)-trimethyl(7-methyloct-1-enyl)silane 
• 113466-79-8 4-methylpentyllithium 
• 113466-78-7 (3-decyloxiran-2-yl)methyl 4-methylbenzenesulfonate 
• 35354-39-3 cis-2-Methyl-7-octadecen 
• 112-41-4 1-dodecene 
• 93108-04-4 (Z)-pentadecen-4-en-1-yl 4-methylbenzenesulfonate 
• 40642-44-2 (Z)-pentadec-4-en-1-ol 
• 90359-69-6 (Z)-1-iodo-7-methyl-1-octene 
• 90359-70-9 n-decylzincchloride 
• 62016-94-8 2-Methylpent-5-ylchlorid 
• 118864-33-8 7-methyl-1-octyne 
• 35354-37-1 5-methylhexyl bromide 

Relevant articles and documents

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.

Stereoselective cometathesis of 1,5-cyclooctadiene with ethylene as an efficient pathway to Z-ene biologically active natural products

-

A highly stereoselective preparation of syn-1,2-diols from secondary α-allenic alcohols via iodocyclization. Synthesis of (±)-threo-L-factor and (±)-disparlure

The iodocyclization of the N-tosyl carbamates 5 of secondary α-allenic alcohols 4 is described. The reaction sequence involves the addition of iodine to the terminal olefin of the allene moiety of 5 resulting in the formation of an isomeric mixture of Z and E diiodides 6 and 7. This initial process is followed, in the same pot, by reaction of the diiodides with silver carbonate. Hydrolysis of the resulting trans imino carbonates 8 provides syn-1,2-diols 10 in highly diastereoselective (>50:1) and regioselective (>20:1) fashion. Oxazolidinones 9 are minor products that arise from the participation of the carbamate nitrogen atom in the cyclization reaction. The regioselectivity of the cyclization reaction from 6/7 to 8 is highly dependent upon the reaction solvent with the optimum results being obtained in ether/MeCN mixtures (10:1 to 50:1) or CH2Cl2. The synthetic utility of the vinyl iodo diols 10 is demonstrated by the synthesis of (±)-threo-5-hydroxy-4-decanolide (17) ((±)-threo-L-factor) and (±)-cis-7,8-epoxy-2-methyloctadecane (24) ((±)-disparlure). The key step in each synthesis involves the conversion of the vinyl iodide moiety of 10 into the alkynes 15 or 18 (from 10j and 10k, respectively) via a high-yielding dehydrohalogenation reaction.