23433-07-0

Usage

Uses

Used in Fragrance Industry:
(R)-(-)-1 3-NONANEDIOL 97 is used as a fragrance ingredient for its sweet and floral aroma, which is highly valued in the perfume, soap, and beauty products industries.
Used in Household Products:
(R)-(-)-1 3-NONANEDIOL 97 is used as a flavor and fragrance ingredient in various household products, enhancing their pleasant smell and making them more appealing to consumers.
Used in Pharmaceutical Manufacturing:
(R)-(-)-1 3-NONANEDIOL 97 is used as a raw material in the manufacturing of pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Plastics Industry:
(R)-(-)-1 3-NONANEDIOL 97 is used as a component in the production of plastics, improving their properties and performance.
Used in Lubricants:
(R)-(-)-1 3-NONANEDIOL 97 is used in the formulation of lubricants, enhancing their efficiency and performance.
Used in Insect Attractants and Pheromones:
(R)-(-)-1 3-NONANEDIOL 97 is used in the development of insect attractants and pheromones due to its ability to attract certain insect species, making it valuable in agricultural and pest control applications.

InChI:InChI=1/C9H20O2/c1-2-3-4-5-6-9(11)7-8-10/h9-11H,2-8H2,1H3

Upstream product

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Relevant academic research and scientific papers

Chemistry of Fruit Flies. Composition of the Rectal Gland Secretion of (Male) Dacus cucumis (Cucumber Fly) and Dacus halfordiae. Characterization of (Z,Z)-2,8-Dimethyl-1,7-dioxaspiroundecane

Combined gas chromatography-mass spectrometry and synthesis have established that the major components of the rectal gland secretion of adult male cucumber flies (Dacus cucumis) are the E,E, E,Z, and Z,Z diastereomers of 2,8-dimethyl-1,7-dioxaspiroundecane, which have been synthesized utilizing organomercury chemistry from 1,10-undecadien-6-one.The thermodynamically least stable Z,Z diastereomer has been characterized for the first time, by 1H and 13C NMR measurements and mass spectrometry.Minor amounts of 3-hydroxy-2,8-dimethyl-1,7-dioxaspiroundecane and various derivatives of the 1,6-dioxaspirodecane and 1,7-dioxaspirododecane systems are also present. 1,3-Nonanediol occurs in significant amounts, and both enantiomers have been acquired by Sharpless asymmetric epoxidation of (E)-2-nonen-1-ol followed by Red-Al (Aldrich) reduction of the chiral epoxy alcohols.Chiral gas chromatographic analysis of the diols (as their cyclic carbonates) has demonstrated that the natural material is the R-(-) enantiomer.Natural (E,Z)-2,8-dimethyl-1,7-dioxaspiroundecane is shown to be racemic, whereas the more abundant E,E diastereomer is enantiomerically highly pure, possessing the 2S,6R,8S configuration.The major volatile component of the rectal gland secretion of male Dacus halfordiae (Tryon) is also (E,E)-2,8-dimethyl-1,7-dioxaspiroundecane, with no detectable levels of the E,Z or Z,Z isomers.Other spiroacetals present were 2-ethyl-7-methyl-1,6-dioxaspirodecane and the unusual even carbon-numbered (E,E)-2-ethyl-8-methyl-1,7-dioxaspiroundecane. 6-Oxo-1-nonanol, diethyl succinate, and 2-methyl-6-pentyl-3,4-dihydro-2H-pyran were also identified.

Ligand-Controlled Regiodivergent Copper-Catalyzed Alkylboration of Alkenes

A novel copper-catalyzed regiodivergent alkylboration of alkenes with bis(pinacolato)diboron and alkyl halides has been developed. The regioselectivity of the alkylboration was controlled by subtle differences in the ligand structure. The reaction thus enables the practical, regiodivergent synthesis of two different alkyl boronic esters with complex structures from a single alkene. One way or another: The copper-catalyzed regiodivergent alkylboration of alkenes with bis(pinacolato)diboron and alkyl halides is described. The regioselectivity of the carboboration can be controlled by fine-tuning the ligand structure.

Copper-Catalyzed Stereospecific Hydroboration of Internal Allylic Alcohols

An effective Cu-catalyzed stereospecific hydroboration of aliphatic and aromatic 1,1,2-trisubstituted internal allylic alcohols has been reported. This reaction proceeds via a silyl ether transient protection of allylic alcohols and subsequent stereospecific hydroboration. Followed by an oxidative workup, an array of acyclic, cyclic, and heterocyclic 1,3-diols was synthesized in good to excellent yields with good functional group tolerance and excellent diastereomeric ratios (> 20:1).

Regio- and Stereoselective Homologation of 1,2-Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3-Diols and Sch 725674

1,2-Bis(boronic esters), derived from the enantioselective diboration of terminal alkenes, can be selectively homologated at the primary boronic ester by using enantioenriched primary/secondary lithiated carbamates or benzoates to give 1,3-bis(boronic esters), which can be subsequently oxidized to the corresponding secondary-secondary and secondary-tertiary 1,3-diols with full stereocontrol. The transformation was applied to a concise total synthesis of the 14-membered macrolactone, Sch 725674. The nine-step synthetic route also features a novel desymmetrizing enantioselective diboration of a divinyl carbinol derivative and high-yielding late-stage cross-metathesis and Yamaguchi macrolactonization reactions.

Oxygen-directed intramolecular hydroboration

Metal-free homoallylic oxygen-directed intramolecular hydroboration is reported. Regioselectivities from 20:1 to 82:1 favoring the 1,3-dioxy-substituted products have been achieved using Me2S·BH3/TfOH followed by standard oxidative workup. Branching at the C5 position improves regioselectivity. Copyright

Hindered organoboron groups in organic chemistry. 21. The reactions of dimesitylboron stabilised carbanions with oxiranes

Dimesitylboron stabilised carbanions react with oxiranes to give products that can be oxidised to 1,3-diols. The reactions are, in general, under steric rather than electronic control, and proceed smoothly for all but tetrasubstituted oxiranes. Some unusual stereoselective effects have been observed.

Synthetically Useful β-Lithioalkoxides from Reductive Lithiation of Epoxides by Aromatic Radical Anions

Epoxides are reductively cleaved by means of lithium 4,4'-di-tert-butylbiphenylide.Ethylene oxide itself cleaves to lithium 2-lithioethoxide (15) in less than 5 min at -95 deg C.Epoxides possessing one unsubstituted carbon atom reduce in a matter of minutes at -78 deg C.When both carbon atoms are monosubstituted, at least 1 h is required.Epoxides with one or with two geminal saturated substituents open mainly between the oxygen atom and the least substituted carbon atom.Ring opening in the other direction leads to an unstable β-lithioalkoxide which very rapidly forms an olefin.Acyclic 1,2-disubstituted epoxides yield only olefins.Cyclooctene oxide produces, after protonation, a 3:7 ratio of cyclooctanol and cyclooctene.Cyclohexene oxide gives a 3:1 ratio of cyclohexanol and cyclohexene.Vinyloxiranes, on the other hand, open at the most substituted C-O bond to produce an allylic anion associated with an alkoxide.The carbanionic centers of the resulting dianions add to the carbonyl groups of aldehydes and ketones; however, when a hydrogen atom is present on the carbon atom which is attached to both negatively charged atoms, some reduction of the carbonyl group competes with the nucleophilic addition.The allylic anions derived from vinyloxiranes, after treatment with titanium tetraisopropoxide or cerium(III) chloride, add to aldehydes mainly at the most or least substituted terminus, respectively.In the former case, the configuration of the resulting glycols is predominantly anti.A number of adducts of the dianions with conjugated unsaturated aldehydes and ketones can be converted to unsaturated cyclic 6-membered ring ethers in the presence of acid or methanesulfonyl chloride.

SILAFUNCTIONAL COMPOUNDS IN ORGANIC SYNTHESIS. 30. INTRAMOLECULAR HYDROSILATION OF ALKENYL ALCOHOLS: A NEW APPROACH TO THE REGIOSELECTIVE SYNTHESIS OF 1,2- AND 1,3-DIOLS

Intramolecular hydrosilation of allyl and homoallyl alcohols and the subsequent oxidative cleavage of the resultant carbon-silicon bond have provided a new approach to the regio-controlled synthesis of 1,2- and/or 1,3-diols.

THE DIMESITYLBORON GROUP IN ORGANIC SYNTHESIS 8. PREPARATION OF 1,3-DIOLS FROM OXIRANES

Alkyldimesitylboranes, yield anions, Mes2BCHR, that on reaction with oxiranes followed by oxidation give 1,3-diols.These anions are thus the operational equivalent of RCHOH.The scope and limitations of the new process are delineated.