67601-05-2

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H22O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,11H,5,7-9H2,1-4H3

Upstream product

• 106-22-9 Citronellol 
• 108-24-7 acetic anhydride 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 108-05-4 vinyl acetate 
• 2436-90-0 (S)-(+)-dihydromyrcene 

Downstream Products

• 82426-10-6 (3S)-3-methyl-6-oxohexan-1-yl acetate 
• 130647-98-2 (3S)-7-hydroxy-3,7-dimethyl-6-oxooctan-1-yl acetate 
• 26759-58-0 Acetic acid (S)-6,7-dihydroxy-3,7-dimethyl-octyl ester 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 2111-53-7 (S)-(-)-citronellic acid 
• 131906-85-9 (5S,7RS,9S)-5,9-Dimethyl-7-phenylsulfonyloctadecane 
• 131906-84-8 (5S,7RS,9S)-5,9-Dimethyl-7-(phenylsulfonyl)heptadecane 
• 131906-81-5 (S)-3-Methyldodecyl Tosylate 
• 131906-80-4 (S)-1-(p-toluenesulfonyloxy)-3-methylundecane 
• 131906-83-7 (S)-3-Methyl-1-(phenylsulfonyl)dodecane 
• 121404-71-5 (S)-(+)-1-phenylsulfonyl-3-methylundecane 
• 121404-70-4 (S)-1-phenylsulfide-3-methylundecane 
• 108195-53-5 (5S,9S)-5,9-Dimethylheptadecane 
• 82425-95-4 (S)-(-)-(4-methyl-6-(tetrahydropyranyloxy)hexane)-triphenylphosphonium iodide 

Relevant academic research and scientific papers

Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid-Producing Plants

Biosynthesis of (1R,4aS,7S,7aR)-nepetalactol (1) and (4aS,7S,7aR)-nepetalactone (2) in plants involves iridoid synthase (ISY), an atypical reductive cyclase that catalyses the reduction of 8-oxogeranial into the reactive enol of (S)-8-oxocitronellal, and cyclization of this enol intermediate, either non-enzymatically or by a nepetalactol-related short chain dehydrogenase enzyme (NEPS) that yields the nepetalactols. In this study, we investigated the biosynthesis in vivo of 1 and 2 in the pea aphid, Acyrthosiphon pisum, using a library of isotopically-labelled monoterpenoids as molecular probes. Topical application of deuterium-labelled probes synthesized from geraniol and nerol resulted in production of 2H4?lactol 1 and 2H4?lactone 2. However, deuterium incorporation was not evident using labelled probes synthesized from (S)-citronellol. These results suggest that iridoid biosynthesis in animals, specifically aphids, may follow a broadly similar route to that characterised for plants.

Relative stereochemical assignment of C-33 and C-35 in the antibiotic gladiolin

Gladiolin is a macrolide antibiotic isolated from Burkholderia gladioli BCC0238 with promising activity against Mycobacterium tuberculosis, including several multidrug resistant strains. The configuration of all but one of the stereogenic centers of gladiolin has previously been elucidated using a combination of NOESY NMR experiments and predictive sequence analysis of the polyketide synthase responsible for its assembly. However, it was not possible to assign the configuration of the C-35 methyl group using such methods. Here we report the synthesis of C-33/C-35-syn and C-33/C-35-anti mimics of the C-30 to C-38 fragment of gladiolin from (R) and (S)-citronellol, respectively. Comparison of HSQC NMR data for the mimics and the natural product showed that the C-35 methyl is anti to the C-33 hydroxyl group, indicating that gladiolin has the 35S configuration.

Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 6,14-dimethyl-2-octadecanone, and 14-methyl-2-octadecanone, the components of the female-produced sex pheromone of a moth, Lyclene dharma dharma

All of the stereoisomers of the components of the female-produced sex pheromone of a moth, Lyclene dharma dharma, were synthesized. They are (R)- and (S)-6-methyl-2-octadecanone, (6R,14R)-, (6R,14S)-, (6S,14R)-, and (6S,14S)-6,14-dimethyl-2-octadecanone, and (R)- and (S)-14-methyl-2-octadecanone. Enantiomers of citronellal and methyl (S)-3-hydroxy-2-methylpropanoate were the starting materials, and olefin cross metathesis was employed as the key reaction.

LAULIMALIDE ANALOGS AND USES THEREOF

The present invention provides compounds having formula 1: (I) and pharmaceutically acceptable derivatives thereof, wherein R1-R10, q, t, X0, X1, A, B, D, E, G, J, K, L, M and Z are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders associated with cellular hyperproliferation.

Synthesis of the 1,5-dimethylic chiron enantiomers, 3,7,11-trimethyldodec-10-en-1-ol: Application to enantiomeric syntheses of tribolure and a marine fatty acid

A convenient synthesis of the title chiron antipodes has been developed starting from (±)-citronellol via a sequential acetylation protocol using two lipases. The different stereoisomers of the chiron were then functionalized by simple routes to (4R,8R)-dimethyldecanal, an insect pheromone and (5R,9R)-5,9,13-trimethyltetradecanoic acid, a marine phospholipid fatty acid.

A convenient synthesis of (4R,7Z,11Z)-(-)-4-methylheptadeca-7,11-dienal and (4R,7Z,11Z)-4-methylheptadeca-7,11-dienoic acid

A synthesis of the title aldehyde 1 and acid 2, the (R) enantiomers of the antifungal and antibacterial principles of Sporothrix species, was developed. Alkylation of the alkynol derivative 6 with (S)-citronellyl bromide (5), depyranylation, cis hydrogenation, PCC oxidation, and Z-selective Wittig reaction with hexylidenephosphorane gave the hydrocarbon 11. Its regioselective epoxidation and cleavage of the epoxide with HlO4 affords (R)-1 which was oxidized to (R)-2. VCH Verlagsgesellschaft mbH, 1996.

The aphid sex pheromone cyclopentanoids: Synthesis in the elucidation of structure and biosynthetic pathways

Identification of a range of aphid sex pheromones as comprising the cyclopentanoids (4aS,7S,7aR)-nepetalactone, (1R,4aS,7S,7aR)-nepetalactol and the (1S)- and (1R,4aR,7S,7aS)-nepetalactols required samples authenticated by 1H and 13C NMR. These and related compounds were provided by small scale synthesis and extraction from plants in the genus Nepeta (Lamiaceae). The subsequent discovery that the synthetic sex pheromones could attract males, and also parasitic wasps that attack aphids, has created a need for large scale syntheses of the cyclopentanoids. This is afforded by cyclisation of the 8-oxo-1-enamine of citronellal as originally developed by Schreiber and co-workers (1986). Investigation into the biosynthesis of the cyclopentanoids by plants for exploiting aphid sex pheromones in crop protection by means of molecular biology required synthesis of putative biosynthetic intermediates, some with radioactive isotopic labelling, particularly 8-oxidised monoterpene alcohols and aldehydes.

Oxyanion Orientation in Anionic Oxy-Cope Rearrangements

Efficiency of chirality transfer in anionic oxy-Cope rearrangement depends solely on the orientational preference of the oxyanionic bond in the substrates with a single carbinol carbon chiral center.In chairlike transition-state conformations for the rearrangement of simplest substrates like anions generated from (E)-1-phenyl-1,5-hexadien-3-ol and (E)-1,5-heptadien-4-ol, the oxyanionic bond is more prone to adopt the pseudoaxial orientation.On the other hand, anions generated from (E)-2-methyl-1,5-heptadien-4-ol, (E)-5-tert-butyl-1-phenyl-1,5-hexadien-3-ol, and 4-(2'-methyl-1'-cyclohexenyl)-1-buten-3-ol undergo rearrangement via chairlike transition states in which the pseudoequatorial oxyanionic bond is favored.It can thus be surmized that there is a slight stereoelectronic preference for the pseudoaxial oxyanionic bond in the chairlike transition states for the rearrangement of substrates without steric constraints.Substitution at C5 of the basic 1,5-hexadien-3-ol framework of substrates, however, leads to 1,3-diaxial steric interaction in the chairlike transition states with pseudoaxial oxyanionic bond, and pseudoequatorial disposition of oxyanionic bond becomes more favorable.