638189-46-5

Basic information

• Product Name: 2-Heptanone, 4-hydroxy-6-methyl-, (4R)- (9CI)
• Synonyms: 2-Heptanone, 4-hydroxy-6-methyl-, (4R)- (9CI)
• CAS NO: 638189-46-5
• Molecular Formula: C8H16O2
• Molecular Weight: 144.21144
• Product Categories: ACETYLGROUP
• Mol File: 638189-46-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Heptanone, 4-hydroxy-6-methyl-, (4R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Heptanone, 4-hydroxy-6-methyl-, (4R)- (9CI)(638189-46-5)
• EPA Substance Registry System: 2-Heptanone, 4-hydroxy-6-methyl-, (4R)- (9CI)(638189-46-5)

Safety Data

• Hazardous Substances Data: 638189-46-5(Hazardous Substances Data)

Usage

Chirality

Chiral compound

Stereochemistry

(4R)

Functional groups

Ketone, hydroxyl group, methyl group

Chain length

Seven carbon chain

Applications

Production of fragrances and flavors, solvent, organic synthesis

Importance

Intermediate in chemical synthesis, creation of pharmaceuticals

Upstream product

• 67-64-1 acetone 
• 590-86-3 isovaleraldehyde 
• 20859-10-3 (3E)-6-methylhept-3-en-2-one 
• 887763-36-2 (R)-4-Hydroxy-6-methyl-hept-6-en-2-one 
• 108-05-4 vinyl acetate 
• 57548-36-4 4-hydroxy-6-methylheptan-2-one 
• 887763-35-1 Formic acid (R)-3-methyl-1-(2-oxo-propyl)-but-3-enyl ester 

Relevant articles and documents

Complete Switch of Reaction Specificity of an Aldolase by Directed Evolution In Vitro: Synthesis of Generic Aliphatic Aldol Products

A structure-guided engineering of fructose-6-phosphate aldolase was performed to expand its substrate promiscuity toward aliphatic nucleophiles, that is, unsubstituted alkanones and alkanals. A “smart” combinatorial library was created targeting residues D6, T26, and N28, which form a binding pocket around the nucleophilic carbon atom. Double-selectivity screening was executed by high-performance TLC that allowed simultaneous determination of total activity as well as a preference for acetone versus propanal as competing nucleophiles. D6 turned out to be the key residue that enabled activity with non-hydroxylated nucleophiles. Altogether 25 single- and double-site variants (D6X and D6X/T26X) were discovered that show useful synthetic activity and a varying preference for ketone or aldehyde as the aldol nucleophiles. Remarkably, all of the novel variants had completely lost their native activity for cleavage of fructose 6-phosphate.

Improved conditions for the proline-catalyzed aldol reaction of acetone with aliphatic aldehydes

The proline-catalyzed asymmetric aldol reaction between aliphatic aldehydes and acetone has, to date, remained underdeveloped. Challenges in controlling this reaction include avoiding undesired side reactions such as aldol condensation and self-aldolization. In recent years we have developed optimized conditions, which enable high yields and good to excellent enantioselectivities, and which are presented in this communication. Georg Thieme Verlag Stuttgart New York.

Direct asymmetric aldol reactions in aqueous media catalyzed by a β-cyclodextrin-proline conjugate with a urea linker

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The first examples of catalytic asymmetric ring-closing metathesis (ARCM) reactions of enol ethers are reported. To identify the most effective catalysts, various chiral Mo- and Ru-based catalysts were screened. Although chiral Ru catalysts (those that do

Preparation of the Enantiomerically Enriched Isomers of the Odorous Cyclic Ethers Clarycet, Florol, and Rhubafuran by Enzymatic Catalysis

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High-pressure-promoted asymmetric aldol reactions of ketones with aldehydes catalyzed by L-proline

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Direct asymmetric aldol reactions of acetone using bimetallic zinc catalysts

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Proline-catalyzed asymmetric aldol reactions between ketones and alpha-unsubstituted aldehydes.

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