246545-38-0

Basic information

• Product Name: (3-NONYL-2-OXIRANYL)METHANOL
• Synonyms: (3-NONYL-2-OXIRANYL)METHANOL
• CAS NO: 246545-38-0
• Molecular Formula: C12H24O2
• Molecular Weight: 200.32
• Mol File: 246545-38-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3-NONYL-2-OXIRANYL)METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (3-NONYL-2-OXIRANYL)METHANOL(246545-38-0)
• EPA Substance Registry System: (3-NONYL-2-OXIRANYL)METHANOL(246545-38-0)

Safety Data

• Hazardous Substances Data: 246545-38-0(Hazardous Substances Data)

Upstream product

• 22104-81-0 (2E)-dodec-2-en-1-ol 
• 69064-36-4 (Z)-dodec-2-en-1-ol 
• 69064-46-6 dodec-2-yn-1-ol 
• 2243-98-3 1-undecyne 
• 706820-72-6 (2S,3R)-3-nonyloxiranemethanol 3,5-dinitrobenzoate 
• 51148-67-5 10-undecen-1-yl p-toluenesulfonate 
• 112-38-9 10-undecenoic acid 
• 112-43-6 10-Undecen-1-ol 
• 821-95-4 1-undecene 
• 112-31-2 caprinaldehyde 
• 42778-95-0 ethyl (E)-dodec-2-enoate 
• 112-30-1 1-Decanol 
• 31502-14-4 2-nonenyl alcohol 

Relevant articles and documents

Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol

We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(?)-carvone by avoiding otherwise necessary protection/deprotection steps.

Total synthesis and in vitro bioevaluation of clavaminols A, C, H & deacetyl clavaminol H as potential chemotherapeutic and antibiofilm agents

A highly concise and expedient total synthesis of bioactive clavaminols (1-4) has been executed using commercially available achiral compound decanol. The synthetic strategy relied on trans-Wittig olefination, Sharpless asymmetric epoxidation, regioselective azidolysis and in situ detosylation followed by reduction as key reactions with good overall yield. Based on biological evaluation studies of all the synthesized compounds, it was observed that the clavaminol A (1) exhibited good cytotoxicity against DU145 and SKOV3 cell lines with IC50 value of 10.8 and 12.5 μM, respectively. Clavaminol A (1) and deacetyl clavaminol H (3) displayed selective promising inhibition towards Gram-positive pathogenic bacterial strains and showed good antifungal activity against the tested Candida strains. In addition, compounds 1 and 3 have demonstrated significant bactericidal activity. Compound 3 was found to be equipotent to the standard drug Miconazole displaying MFC value of 15.6 μg/mL against Candida albicans MTCC 854, C. albicans MTCC 1637, C. albicans MTCC 3958 and Candida glabrata MTCC 3019. Compounds 1 and 3 were also able to inhibit the biofilm formation of Micrococcus luteus MTCC 2470 and Staphylococcus aureus MLS16 MTCC 2940. Clavaminol A (1) increased the levels of reactive oxygen species (ROS) accumulation in M. luteus MTCC 2470.

Scalable synthesis of the pink gypsy moth Lymantria mathura sex pheromone (-)-mathuralure

Mathuralure (1) is the major sex pheromone component of the pink gypsy moth Lymantria mathura, a potentially devastating invasive species to North America. To support population monitoring of this moth, a gram-scale synthesis of (-)-mathuralure (1) was developed. This process relies on coupling an alkynyl lithium species with a chloroepoxide and provides access to the natural product in a 10% yield over 10 steps.

Total synthesis and antifungal activity of (2S,3R)-2-aminododecan-3-ol

We report the total synthesis of (2S,3R)-2-aminododecan-3-ol has been achieved starting from commercially available 10-undecenoic acid. The key steps involved are Sharpless asymmetric epoxidation, Miyashita's boron-directed C-2 regioselective azidolysis, generated the asymmetric centers and in situ detosylation and reduction of azido tosylate. The antifungal activity of the synthesized (2S,3R)-2-aminododecan-3-ol was evaluated on several Candida strains and was comparable to miconazole, a standard drug.

An efficient synthesis of (-)-posticlure: The sex pheromone of Orgyia postica

An efficient multigram synthesis of (-)-posticlure, the first frans-epoxide sex pheromone found in Orgyia postica, from diethyl L-tartrate is described. The synthesis was completed in seven steps and 27 % overall yield. The synthetic strategy features double-Wittig olefination and a stereoselective one-pot conversion of diol to epoxide as the key steps. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Improved Synthesis and Deployment of (2S,3R)-2-(2Z,5Z-Octadienyl)-3-nonyloxirane, a Pheromone of the Pink Moth, Lymantria mathura

We report two new syntheses of (2S,3R)-2-(2Z,5Z-octadienyl)-3-nonyloxirane, the main sex pheromone component of the pink moth, Lymantria mathura. The key step in the first route was the construction of (Z,Z)-1-bromo-1,4-heptadiene (6), which was coupled i

Posticlure: A novel trans-epoxide as a sex pheromone component of the tussock moth, Orgyia postica (Walker)

A single EAG-active component was found in a pheromone extract from virgin females of the tussock moth, Orgyia postica. This compound named posticlure possesses a trans-epoxy ring and was identified as (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene by means of GC-MS, 1H NMR and chiral HPLC analyses, and further chemical derivation followed by the GC-MS analysis. In a field test with the pheromone synthesized stereoselectivity, the male moths were specifically attracted to the (11S,12S)-isomer but not to the antipode.

Fleming-Tamao oxidation and masked hydroxyl functionality: Total synthesis of (+)-pramanicin and structural elucidation of the antifungal natural product (-)-pramanicin

The total synthesis of (+)-pramanicin (41b) is reported, thereby establishing the relative and absolute stereochemistry of the naturally occurring antifungal agent. The key steps involve (i) conjugate addition of the diethyl((diethylamino)diphenylsilyl)zincate to a suitably protected γ- lactam 3 and quenching of the resultant enolate with the α,β-unsaturated γ,δ-epoxy aldehyde 2 (X = H), (ii) Ni(acac)2-catalyzed hydroxylation of a β-dicarbonyl array, and (iii) Fleming-Tamao oxidation to reveal the masked C-3 hydroxyl group.

Asymmetric synthesis using diisopropyl tartrate modified (E)- and (Z)-crotylboronates: Preparation of the chiral crotylboronates and reactions with achiral aldehydes

Diisopropyl tartrate modified (E)- and (Z)-crotylboronates 2 and 3 are easily prepared with very high isomeric purity (≥98% E for 2; ≥99% Z for 3) via the metalation of (E)- and (Z)-2-butene with n-BuLi and KOtBu in THF followed by treatment of the (E)- a

Synthesis of the optical antipodes of 4-alkyl-γ-lactones

Optical antipodes of 4-alkyl-γ-lactones 3 have been prepared by photochemical rearrangement of optically active α,β-epoxy diazomethyl ketones 1 in ethanol to give 4-hydroxy-alkenoates 2, followed by reduction of the alkene bond and subsequent lactonization.The required epoxy diazomethyl ketones 1 were obtained via the following sequence of reactions: alkylation of 2-propyn-1-ol, subsequent reduction to the alkenols 6, Sharpless epoxidation to 2,3-epoxy alcohols 7, oxidation to glycidic esters 8 and finally conversion to diazo ketones 1.The enantiomeric purities range from 84 to 100percent.