86252-54-2

Usage

Uses

Used in Pharmaceutical Industry:
2H-Pyran, tetrahydro-2-(10-tetradecynyloxy)is used as an intermediate in the synthesis of cyclopropyl-containing fatty acids for their application as mechanistic probes for cytochromes P450. This helps researchers understand the role of these enzymes in the metabolism of drugs and other substances, potentially leading to the development of more effective medications and therapies.

Upstream product

• 55695-90-4 2-(9-bromononyloxy)tetrahydropyran 
• 627-19-0 1-Pentyne 
• 51953-88-9 1-[(tetrahydropyran-2-yl)oxy]undec-10-yne 
• 106-94-5 propyl bromide 
• 110-87-2 3,4-dihydro-2H-pyran 
• 55362-80-6 9-bromononan-1-ol 
• 2774-84-7 undec-10-yn-1-ol 
• 34683-71-1 undec-2-yn-1-ol 

Downstream Products

• 86252-66-6 Z,Z-3,14-octadecadien-1-ol acetate 

Relevant academic research and scientific papers

Cyclopropyl containing fatty acids as mechanistic probes for cytochromes P450

(Chemical Equation Presented) The mechanism of aliphatic hydroxylation by cytochromes P450 has been the subject of intense debate with several proposed mechanistic alternatives. Various cyclopropyl containing compounds (radical clocks), which can produce both unrearranged and ring opened products upon oxidation, have been key tools in these investigations. In this study, we introduce several cyclopropyl containing fatty acids 1a-4a with which to probe the mechanism of P450s capable of fatty acid hydroxylation. The probes are shown to be capable of distinguishing radical from cationic intermediates due to the rapid equilibration of isomeric cyclopropyl cations. Ring opening of a radical intermediate in an oxidative transformation is expected to yield a single rearranged alcohol, whereas a cation isomerizes prior to ring opening, leading to two isomeric homoallylic alcohols. Oxidation of these probes by P450 BM3 and P450Biol gives results consistent with a radical but not a cationic intermediate in fatty acid hydroxylation by these enzymes. Quantitation of the unrearranged and ring opened products gives remarkably homogeneous rates for oxygen rebound of (2-3) × 1010 s -1. The effects of introduction of a cyclopropane ring into a fatty acid upon the regiochemistry of hydroxylation are discussed.

PIPERIDINE ALKALOIDS FROM PIPER RETROFRACTUM FRUITS

Two new piperidine alkaloids, piperoctadecalidine and pipereicosalidine have been isolated from the fruits of Piper retrofractum (Piperaceae) along with two known piperidine alkaloids piperine and pipernonaline.The structures of the new compounds were determined to be (2E,4E,14Z)-N-(2,4,14-octadecatrienoyl)piperidine and (2E,4E,16Z)-N-(2,4,16-eicosatrienoyl)piperidine, respectively, by spectral and synthetic methods.Key Word Index: Piper retrofractum; Piperaceae; fruits; piperidine alkaloids; piperoctadecalidine; pipereicosalidine.

(E,Z)-2,13-OCTADECADIEN-1-OL ACETATE. A NEW FEROMONE STRUCTURE FOR SESIID MOTHS

(E,Z)-2,13-Octadecadien-1-ol acetate was identified from ovipositor extracts of the grape root borer and was shown to attract males of the species.

INSECT SEX PHEROMONES. STEREOSELECTIVE SYNTHESIS OF SEVERAL (Z)- AND (E)-ALKEN-1-OLS, THEIR ACETATES, AND OF (9Z,12E)-9,12-TETRADECADIEN-1-YL ACETATE

Several female sex pheromone components produced by moths belonging to the order of Lepidoptera, and potential attractants of Dacus oleae (Diptera:Tripetidae) have been synthesized in high chemical and stereoisomeric purity by improved acetylenic routes involving alkylation of lithium 1-alkyn-1-ides in HMPT, followed by (Z) and (E) highly stereoselective reduction of the derived internal alkynes.Particular care has been paid to optimize the parameters of the reactions used and to evaluate the chemical and isomeric purity of the reaction products.The compounds synthesized include (Z)- and (E)-5-nonen-1-ol, (Z)- and (E)-7-dodecen-1-yl acetate, (Z)- and (E)-7-teradecen-1-yl acetate, (Z)- and (E)-7-nonen-1-ol, (Z)- and (E)-9-tetradecen-1-yl acetate, (Z)- and (E)-10-tetradecen-1-yl acetate, (Z)- and (E)-11-tetradecen-1-yl acetate.Pure (Z)-6-nonen-1-ol, which is an attractant of olive fruit fly, D. oleae, and very probably, a constituent of the sex pheromone of females of this insect, has been prepared by a rather efficient copper-catalyzed reaction between (Z)-3-hexen-1-ylmagnesium bromide and oxetane. (9Z,12E)-9,12-Tetradecadien-1-yl acetate, which is the pheromone of Anagasta kuenniella, Ephestia elutella, Cadra figulella, Spodoptera exigua, S. litura, and a component of the sex pheromones of several other Lepidoptera, has been conveniently prepared by using the copper-catalyzed coupling reaction between (E)-1-chloro-2-butene and 10-tetrahydropyranyloxy-1-decenylmagnesium bromide, followed by acetylation and Z-stereoselective reduction of the derived 1,4-enyne.All syntheses have been conducted on a scale to yield less than 50 mmol of the pure sex pheromone components, but seem adaptable for much larger quantities.