128899-83-2

Basic information

• Product Name: (3R,5R)-2,6-Dimethyl-3,5-heptanediol
• Synonyms: (3R,5R)-2,6-Dimethyl-3,5-heptanediol;(3R,5R)-2,6-Dimethylheptane-3,5-diol
• CAS NO: 128899-83-2
• Molecular Formula: C₉H₂₀O₂
• Molecular Weight: 160.25
• Mol File: 128899-83-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R,5R)-2,6-Dimethyl-3,5-heptanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5R)-2,6-Dimethyl-3,5-heptanediol(128899-83-2)
• EPA Substance Registry System: (3R,5R)-2,6-Dimethyl-3,5-heptanediol(128899-83-2)

Safety Data

• Hazardous Substances Data: 128899-83-2(Hazardous Substances Data)

Usage

Uses

Used in Coatings Industry:
(3R,5R)-2,6-Dimethyl-3,5-heptanediol is used as a component in the manufacturing of coatings for its ability to enhance flexibility and durability.
Used in Adhesives Industry:
(3R,5R)-2,6-Dimethyl-3,5-heptanediol is used as a component in the production of adhesives to improve the moisture resistance and overall performance of the adhesives.
Used in Plasticizers Industry:
(3R,5R)-2,6-Dimethyl-3,5-heptanediol is used as a plasticizer to increase the flexibility and workability of plastics.
Used in Polyester Resins Industry:
(3R,5R)-2,6-Dimethyl-3,5-heptanediol is used in the production of polyester resins to improve their properties.
Used in Lubricants Industry:
(3R,5R)-2,6-Dimethyl-3,5-heptanediol is used as a component in the formulation of lubricants to enhance their performance.
Used in Pharmaceuticals Industry:
(3R,5R)-2,6-Dimethyl-3,5-heptanediol is used in the production of certain types of pharmaceuticals, likely due to its solubility and other chemical properties.
Used in Organic Synthesis:
(3R,5R)-2,6-Dimethyl-3,5-heptanediol is utilized as a building block in the synthesis of various organic compounds, contributing to the creation of a wide range of industrial and consumer products.

Upstream product

• 1438-14-8 2-isopropyloxirane 
• 78-84-2 isobutyraldehyde 
• 65429-68-7 5-hydroxy-2,6-dimethyl-heptan-3-one 
• 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 
• 18362-64-6 2,6-dimethyl-3,5-heptanedione 
• 107-11-9 1-amino-2-propene 
• 100-46-9 benzylamine 
• 563-80-4 3-methyl-butan-2-one 
• 97-72-3 2-Methylpropionic anhydride 
• 105-53-3 diethyl malonate 
• 121440-79-7 (+/-)-(E)-2,6-dimethylhept-4-en-3-ol 

Downstream Products

• 2344-70-9 1-phenyl-3-butanol 
• 1243579-23-8 2,6-dimethyl-5-octylsulfanylheptan-3-one 

Relevant articles and documents

Synthesis of Enantiomerically Pure β-Hydroxy Ketones via β-Keto Weinreb Amides by a Condensation/Asymmetric-Hydrogenation/Acylation Sequence

An established route to enantiomerically pure β-hydroxy ketones proceeds through the asymmetric hydrogenation of β-keto esters, an ester/amide exchange, and the use of the resulting β-hydroxy amide for the acylation of an organometallic compound. We shortened this route by showing that β-keto Weinreb amides are hydrogenated with up to 99 % ee in the presence of [Me2NH2]+{[RuCl(S)-BINAP]2(μ-Cl)3}–(0.5 mol-%) at room temp./5 bar. These Weinreb amides were prepared by seemingly obvious yet unprecedented condensations of lithiated N-methoxy-N-methylacetamide with carboxylic chlorides (51–87 % yield). The resulting β-hydroxy Weinreb amides were used for the acylation of organolithium and Grignard reagents. They thus gave enantiomerically pure β-hydroxy ketones (28 examples). A selection of these compounds gave anti-1,3-diols after another C=O bond hydrogenation, or syn-1,3-diols by a Narasaka–Prasad reduction.

Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones

Towards the synthesis of sterically hindered optically active secondary alcohol 2, yeast strains (Candida floricola IAM 13115 and Trichosporon cutaneum IAM 12206) with si-face hydride attack on isopropyl phenylsulfonylmethyl ketone 1 were developed by scr

The zirconium alkoxide-catalyzed aldol-tishchenko reaction of ketone aldols

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.

Ligands for asymmetric catalysis

The subject invention relates to phosphine ligands that are useful for asymmetric reactions, especially as chiral ligands for catalytic asymmetric hydrogenation.

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

Methylation of methyl 4-phenylpentanoate 25 gives the diastereoisomers methyl (2RS,4SR)-2-methyl-4-phenylpentanoate 26 and methyl (2RS,4RS)- 2-methyl-4-phenylpentanoate 27 in a ratio of 44:56. The aldehydes 3-dimethyl(phenyl)silylbutanal 28, 3-dimethyl(ph

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.

Asymmetric Synthesis of (3R,5R)- and (3S,5S)-2,6-Dimethylheptane-3,5-diol, useful C2 Chiral Auxiliaries

(R,R)- and (S,S)-2,6-Dimethylheptane-3,5-diol, which are useful C2 chiral auxiliaries, have been both synthesized in high optical purity from 2,6-dimethylheptane-3,5-dione, by using as key step a Sharpless kinetic resolution.