57403-74-4

Basic information

• Product Name: (R)-3-METHYLHEPTANOIC ACID
• Synonyms: (R)-3-METHYLHEPTANOIC ACID;(3R)-3-Methylheptanoic acid
• CAS NO: 57403-74-4
• Molecular Formula: C₈H₁₆O₂
• Molecular Weight: 144.21
• Mol File: 57403-74-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-3-METHYLHEPTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-METHYLHEPTANOIC ACID(57403-74-4)
• EPA Substance Registry System: (R)-3-METHYLHEPTANOIC ACID(57403-74-4)

Safety Data

• Hazardous Substances Data: 57403-74-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-METHYLHEPTANOIC ACID is used as a precursor or intermediate for the synthesis of various pharmaceuticals and other organic compounds, contributing to the development of new medications and therapeutic agents.
Used in Flavor and Fragrance Industry:
(R)-3-METHYLHEPTANOIC ACID is used as a flavoring agent in the food and beverage industry, leveraging its distinctive odor and taste to enhance the sensory experience of products.
Used in Medicinal Chemistry Research:
(R)-3-METHYLHEPTANOIC ACID is utilized in the field of medicinal chemistry, where it is studied for its potential biological and pharmacological properties, indicating its value in the discovery and understanding of new therapeutic agents.

Upstream product

• 84817-84-5 3-methylideneheptanoic acid 
• 3200-11-1 1-phenyl-2-methylhexane 
• 198956-42-2 (2S)-2-Benzylhexane 
• 109-65-9 1-bromo-butane 
• 199006-79-6 (R)-(+)-N-(1-ethyl-2-hydroxy)ethyl-N-(2-fluorobenzyl) crotonamide 
• 96864-26-5 (R)-3-Methyl-heptanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 88020-53-5 (S)-3-Methyl-heptanoic acid ((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 77727-24-3 (E)-2-((S)-Benzenesulfinyl)-but-2-enoic acid methyl ester 
• 105526-90-7 (5S)-N-[(3R)-methylheptanoyl]-5-triphenylmethoxymethyl-2-pyrrolidinone 

Downstream Products

• 1070-32-2 (R)-(+)-3-Methyl-1-heptanol 
• 27608-03-3 (+)-(R)-3-methylheptanal 

Relevant articles and documents

Neutral iridium catalysts with chiral phosphine-carboxy ligands for asymmetric hydrogenation of unsaturated carboxylic acids

We developed neutral iridium catalysts with chiral spiro phosphine-carboxy ligands (SpiroCAP) for asymmetric hydrogenation of unsaturated carboxylic acids. Different from the cationic Crabtree-type catalysts, the iridium catalysts with chiral spiro phosphine-carboxy ligands are neutral and do not require the use of a tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (BArF?) counterion, which is necessary for stabilizing cationic Crabtree-type catalysts. Another advantage of the neutral iridium catalysts is that they have high stability and have a long lifetime in air. The new iridium catalysts with chiral spiro phosphine-carboxy ligands exhibit unprecedented high enantioselectivity (up to 99.4% ee) in the asymmetric hydrogenations of various unsaturated carboxylic acids, particularly for 3-alkyl-3-methylenepropionic acids, which are challenging substrates for other chiral catalysts.

Rh-catalyzed highly enantioselective synthesis of 3-arylbutanoic acids

(Chemical Equation Presented) It's in the mix: The reaction conditions - catalyst, additive, and solvent - have been optimized for the asymmetric hydrogenation of 3-aryl-3-butenoic acids. The rigid, chiral bisphospholane ligand (SP,RC)-DuanPhos is crucial to achieving high enantioselectivity.

The 1,4-addition of organometallic reagents to enoates derived from pinanediol

The complex-induced, proximity effect-promoted 1,4-addition of RCu·BF3 and R2CuLi to enoates derived from (-)-pinanediol leads to adducts with the opposite sense of chirality (up to 98% d.e.).

Enantioselective carbometalation of cinnamyl derivatives: New access to chiral disubstituted cyclopropanes - Configurational stability of benzylic organozinc halides

A stoichiometric or catalytic amount of (-)-sparteine can serve asa promoter for the enantioselective carbolithiation of cinnamyl derivatives by primary and secondary organolithium compounds. The enantiofacial choice of the addition reaction is dependent on the stereochemistry of the initial double bond. The resulting benzylic organolithium compounds can be derivatized to a linear phenylated chain that bears two contiguous stereogenic centers with given configurations. The use of the dimethyl acetal of the (E)-cinnamyl alcohol allows the highest enantioselective carbolithiation and by simply warming the reaction mixture to room temperature, the resulting benzylic organo-lithium intermediate undergoes a 1,3-elimination to give the chiral disubstituted cyclopropane in high enantiomeric excess (90-95% ee). Another significant finding is the observation that the Li-Zn transmetalation in a benzylic species occurs with inversion of configuration, and the corresponding acyclic benzylic zinc halides have observable configurational stability at - 30°C.

Enantioselective carbolithiation of β-alkylated styrene

Stoichiometric or catalytic amounts of (-) sparteine serve as promoter for enantioselective carbolithiation of β-alkylated, non functionalized styrene.

Dispiroketals in synthesis (Part 16): Functionalised dispiroketals as new chiral auxiliaries; the synthesis of dihydroxylated dispiroketals in optically pure form and their application as bifunctional , C2-symmetrical, chiral auxiliaries for highly stereoselective Michael additions

A range of rigid, architecturally complex diols derived from dispiroketals have been synthesised.A bifunctional, C2-symmetrical, chiral auxiliary derived from these dihydroxylated dispiroketals has been used to induce a high degree of asymmetry in Michael additions of cuprates to a variety of di-α,β-unsaturated ester systems.

Diastereoselectivity in Iodotrimethylsilane-promoted Conjugate Additions of Organocopper Reagents to Chiral α,β-Unsaturated Imides and Amides

Conjugate additions of MeCu, PhCu and BuCu to the chiral enoylimides 2 a-c in the presence of iodotrimethylsilane and lithium iodide in THF give the adducts, 4a-c in yields above 90percent and diastereoselectivities from 80 to 93percent.The dominating diastereomers are different from those formed with LiR2Cu/TMSCl or in copper(I)-mediated addition of Grignard reagents.Corresponding additions to enoyl-amides of O-tritylprolinol also give high yields of conjugate adducts, but lower diastereoselectivities, with dominating configuration in the acyl part opposite to those from the imides.

Asymmetric Conjugate Addition to Unsaturated Chiral Amido Alcohols Using Grignard Reagents Co-ordinated with Tertiary Amines or DBU. Preparation of Optically Active 3-Substituted Carboxylic Acids and (S)-(-)-Citronellol

Optically active 3-substituted carboxylic acids and (S)-(-)-citronellol have been obtained by diastereoselective conjugate addition of Grignard reagents co-ordinated with 1,8-diazabicyclo-undec-7-ene (DBU) to chiral amidoalcohols derived from (S)-proline.

ASYMMETRIC CONJUGATE ADDITION REACTION BY THE USE OF (S)-γ-TRITYLOXYMETHYL-γ-BUTYROLACTAM AS A CHIRAL AUXILIARY

(S)-γ-Trityloxymethyl-γ-butyrolactam (2) serves as a chiral auxiliary in the conjugate addition reaction of the corresponding imide (3) of α,β-unsaturated carboxylic acids with Grignard reagents in the presence of CuBr-SMe2 in THF to give, after hydrolysis, the β,β-disubstituted carboxylic acids (5) with predictable absolute configuration and high enantiomeric excess.