51532-31-1

Basic information

• Product Name: (+)-(S)-4-methyl-heptane-3-one
• Synonyms: (+)-(S)-4-methyl-heptane-3-one
• CAS NO: 51532-31-1
• Molecular Weight: 128.214
• Mol File: 51532-31-1.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (+)-(S)-4-methyl-heptane-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(S)-4-methyl-heptane-3-one(51532-31-1)
• EPA Substance Registry System: (+)-(S)-4-methyl-heptane-3-one(51532-31-1)

Safety Data

• Hazardous Substances Data: 51532-31-1(Hazardous Substances Data)

Upstream product

• 27771-19-3 (E)-4-methylhept-4-en-3-one 
• 97-61-0 2-Methylpentanoic acid 
• 811-49-4 ethyllithium 
• 49642-47-9 methyl (R)-2-methylbutyric acid 
• 96-22-0 pentan-3-one 
• 1289377-49-6 C₈H₁₇NO₂ 
• 925-90-6 ethylmagnesium bromide 
• 797758-66-8 (4R)-4-benzyl-3-[(2R)-2-methylpentanoyl]-1,3-oxazolidin-2-one 
• 67-64-1 acetone 
• 34405-50-0 4-ethyl-3-methyl-γ-butyrolactone 
• 76291-88-8 (R)-4-Hydroxy-hex-2-ynoic acid 
• 77075-75-3 (3R,4R)-4-Methyl-hept-6-en-3-ol 
• 77075-70-8 (4R,5R)-5-Ethyl-4-methyl-tetrahydro-furan-2-ol 
• 77075-72-0 (R)-4-(Tetrahydro-pyran-2-yloxy)-hex-2-ynoic acid ethyl ester 

Downstream Products

• 1289377-51-0 C₂₂H₃₆O₄ 
• 1289377-52-1 C₂₂H₃₈O₄ 
• 1289377-53-2 C₃₄H₆₆O₄Si₂ 
• 1289377-58-7 C₂₅H₄₂O₄ 

Relevant articles and documents

Enantioselective cyclopropanation of carboxylic esters with alkyl magnesium bromides in the presence of titanium(IV) (4R,5R)-TADDOLates

The reaction of isopropyl 4-chlorobutyrate with 3 equiv of n-BuMgBr in the presence of 1 equiv of titanium(IV) (4R,5R)-TADDOLate in diethyl ether led to the formation of (1S,2S)-(3-chloropropyl)-2-ethylcyclopropanol in 55-70% yield and 55-65% ee. The reaction was performed in the presence of 20 mol % of the catalyst without significant loss in yield and enantioselectivity when solutions of the carboxylic ester and the Grignard reagent were added simultaneously at an equal rate to a refluxing solution of the titanium catalyst in ether. The cyclopropanation of isopropyl propionate under the same conditions gave (1S,2S)-1-ethyl-2-propylcyclopropanol in 50% yield and 65% ee. Its absolute configuration was determined by chemical correlation through acid-catalyzed isomerization to enantiomerically enriched (R)-(-)-4-methyl-3-heptanone, known as a minor component of the trail pheromone of ant Aphaenogaster albisetosus and enantiomer of the alarm pheromone of leaf-cutting ants Atta texana.

Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones

The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.

Total synthesis of hoiamide C

Chemical equations presented. Hoiamide C was synthesized in 16 steps with an overall yield of 1.8% starting from homoallylic alcohol 18, unambiguously confirming its structure.