125873-95-2

Basic information

• Product Name: (3S,5S)-2,6-Dimethyl-3,5-heptanediol
• Synonyms: (3S,5S)-2,6-Dimethyl-3,5-heptanediol
• CAS NO: 125873-95-2
• Molecular Formula: C₉H₂₀O₂
• Molecular Weight: 160.2539
• Mol File: 125873-95-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S,5S)-2,6-Dimethyl-3,5-heptanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5S)-2,6-Dimethyl-3,5-heptanediol(125873-95-2)
• EPA Substance Registry System: (3S,5S)-2,6-Dimethyl-3,5-heptanediol(125873-95-2)

Safety Data

• Hazardous Substances Data: 125873-95-2(Hazardous Substances Data)

Usage

Uses

Used in High-Performance Polymers and Resins:
(3S,5S)-2,6-Dimethyl-3,5-heptanediol is used as a key component in the production of high-performance polymers and resins. Its molecular structure contributes to the enhanced properties of these materials, such as strength, durability, and thermal stability.
Used in Organic Compound Synthesis:
This diol is also utilized as an intermediate in the synthesis of various organic compounds. Its unique structure allows for further chemical reactions, leading to the creation of a wide range of products.
Used in Fragrance Industry:
(3S,5S)-2,6-Dimethyl-3,5-heptanediol is used as a base material for creating fragrances. Its mild odor and compatibility with other fragrance components make it a valuable asset in the development of new scents.
Used in Flavor Industry:
In the flavor industry, (3S,5S)-2,6-Dimethyl-3,5-heptanediol is employed to enhance the taste and aroma of various food and beverage products. Its ability to blend well with other flavor compounds contributes to its widespread use in this sector.
Used in Pharmaceutical Industry:
(3S,5S)-2,6-Dimethyl-3,5-heptanediol is used as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its unique properties and reactivity make it a valuable component in the development of new drugs and medications.

Upstream product

• 18362-64-6 2,6-dimethyl-3,5-heptanedione 
• 1438-14-8 2-isopropyloxirane 
• 78-84-2 isobutyraldehyde 
• 65429-68-7 5-hydroxy-2,6-dimethyl-heptan-3-one 
• 187873-82-1 2,6-Dimethyl-1-heptene-3,5-diol 
• 105627-21-2 2,2-dimethyl-4,6-di-isopropyl-1,3-dioxa-2-silacyclohexane 
• 105627-17-6 2,2,4,6-tetraisopropyl-1,3-dioxa-2-silacyclohexene 
• 75-09-2 dichloromethane 
• 28920-34-5 2,6-dimethyl-5-hepten-3-ol 
• 107-11-9 1-amino-2-propene 
• 100-46-9 benzylamine 
• 563-80-4 3-methyl-butan-2-one 
• 36587-79-8 5-hydroxy-2,5-dimethyl-3-hexanone 
• 105627-13-2 2,6-dimethyl-5-di-isopropylsilyloxyheptan-3-one 

Downstream Products

• 2344-70-9 1-phenyl-3-butanol 
• 1243579-23-8 2,6-dimethyl-5-octylsulfanylheptan-3-one 
• 848873-51-8 ((1R,3S)-1-Isopropyl-4-methyl-3-vinyloxy-pentyloxy)-benzene 
• 125873-96-3 (3S,5S)-5-(Cyclohex-1-enyloxy)-2,6-dimethyl-heptan-3-ol 
• 125787-45-3 (3S,5S)-5-(4,4-Dimethyl-cyclohex-1-enyloxy)-2,6-dimethyl-heptan-3-ol 

Relevant articles and documents

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The aldol-Tishchenko reaction of ketone aldols as enol equivalents has been developed as an efficient strategy to furnish differentiated 1,3-anti-diol monoesters in one step. The thermodynamically unstable ketone aldols undergo a facile retro-aldolization to yield a presumed zirconium enolate in situ, which then undergoes the aldol-Tishchenko reaction in typically high yields and with complete 1,3-anti diastereocontrol. Evaluation of a broad range of metal alkoxides as catalysts and optimization of the reaction protocol led to a modified zirconium alkoxide catalyst with attenuated Lewis acidity and dichloromethane as solvent, which resulted in suppression of the undesired acyl migration to a large extent. Various ketone aldols have been prepared and subjected to the general process, giving rise to a broad range of differently substituted 1,3-anti-diol monoesters, which may be hydrolyzed to the corresponding 1,3-anti-diols.

Enantioselective synthesis ofanti 1, 3-diols via ru(ii)-catalyzed hydrogénations

The homogeneous ruthenium-catalyzed hydrogénation of new symmetrical 1, 3-diketones has been achieved with various ligands including SKEWPHOS and Me-DuPHOS. Complete conversions with enantiomeric and diastereomeric excesses up to 99% were obtained. This represents a new catalytic application of the chiral ligands above. Thieme Stuttgart.

Chiral 1,2-bis(phosphetano)benzenes: Preparation and use in the Ru- catalyzed hydrogenations of carbonyl derivatives

Chiral 1,2-bis(phosphetano)benzenes are readily prepared from accessible, optically pure 1,3-diol cyclic sulfates. Their ruthenium complexes catalyze the enantioselective hydrogenations of functionalized carbonyls with moderate-to-high enantiomeric excesses. High levels of diastereo- and enantioselectivity are achieved, especially in the hydrogenation of β-diketones to the corresponding anti-1,3-diols.

Stereocontrolled reductive amination of 3-hydroxy ketones

syn-1,3-Aminoalcohols are synthesized in high diastereomeric excess by reductive amination of 3-hydroxyketones with sodium cyanoborohydride in the presence of benzylamine.

In search of open-chain 1,3-stereocontrol

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Polychlorinated materials as a source of polyanionic synthons

The reaction of dichloromethane (1a) or dichlorodideuteriomethane (1b) with an excess of lithium powder (1:7 molar ratio) and a catalytic amount of DTBB (5 mol%) in the presence of a carbonyl compound 2 (1:2 molar ratio) in THF at -40°C yields, after hydrolysis, the corresponding 1,3-diols 3 in moderate yields. The process is applied to other gem-dichlorinated materials such as 7,7-dichloro [4.1.0]heptane (4), 1,1-dichlorotetramethylcyclopropane (7) and dichloromethyl methyl ether (10), using pivalaldehyde as electrophile. Starting from 1,1,1-trichlorinated compounds or tetrachloromethane (14) and using chlorotrimethylsilane as electrophile at temperatures ranging between -80 and -90°C, the corresponding polysilylated compounds 15-17 are prepared applying the mentioned methodology.

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Dichloromethane as a source of the CH22-synthon: A combination of an arene-catalysed lithiation and a barbier-type reaction

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