29671-29-2

Usage

InChI:InChI=1/C6H11ClO2/c1-4(2)3-5(7)6(8)9/h4-5H,3H2,1-2H3,(H,8,9)

Upstream product

• 61-90-5 L-leucine 
• 328-39-2 LEUCINE 
• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 
• 646-07-1 4-Methylpentanoic acid 
• 4361-06-2 isobutylmalonic Acid 
• 123488-97-1 2-chloro-4-methyl-pent-2-enoic acid methyl ester 
• 7071-13-8 Ethyl (Z)-2-Chloro-4-Methylpent-2-Enoate 
• 319-78-8 isoleucine 
• 7632-00-0 sodium nitrite 
• 161661-14-9 1-<1,2;5,6-di-O-(1-methylethylidene)-α-D-glucofuranosyloxy>-1-trimethylsilyloxy-4-methyl-pent-1-ene 
• 139193-63-8 1,2;5,6-di-O-(1-methylethylidene)-α-D-glucofuranosyl 4-methyl pentanoate 

Downstream Products

• 541-46-8 isobutylamide 
• 111505-48-7 4-Nitro-benzoic acid (R)-1-tert-butoxycarbonyl-ethyl ester 
• 76379-09-4 benzyl 2-acetamido-4,6-O-benzylidene-3-O-<1-(R)-carboxyisopentyl>-2-deoxy-α-D-glucopyranoside 
• 143238-70-4 2'-<6'-((2''S-2''-chloro-4''-methylpentanoyl)oxy)>naphthyl 4-decyloxybenzoate 
• 111505-51-2 4-Nitro-benzoic acid (R)-1-tert-butoxycarbonyl-3-methyl-butyl ester 
• 1190832-59-7 C₁₂H₁₇ClN₂O 
• 1599459-87-6 (2S)-2-(2′-chloro-4′-methylpentanamido)-4-chlorobenzoic acid 
• 1599459-89-8 (2S)-2-(2′-chloro-4′-methylpentanamido)-5-bromobenzoic acid 
• 83120-46-1 α-(2,3-dichloro-4-methoxyphenylthio)-γ-methyl-n-valeric acid 

Relevant academic research and scientific papers

A facile microwave assisted synthesis and structure elucidation of (3R)-3-alkyl-4,1-benzoxazepine-2,5-diones by crystallographic, spectroscopic and DFT studies

The use of microwave (MW) irradiation in organic synthesis has become increasingly popular within the pharmaceutical and academic arenas because it is a new enabling technology for drug discovery and development. It is a rapid way of synthesis, which involves faster reaction rates and high selectivity to conventional heating method of syntheses. The MW-assisted 7-exo-tet cyclization of N-acylanthranilic acids afforded (3R)-3-alkyl-4,1-benzoxazepines-2,5-diones in very short duration (20 min) with extraordinary high yields in comparison to conventional heating mode of synthesis. The method development, comparative yields of MW-assisted and thermal method of syntheses, crystallographic, spectroscopic and density functional theory (DFT) studies are reported herein. Four novel compounds with chemical formulas C10H9BrClNO3 5m, C19H19NO3 6e, C13H14ClNO3 6h and C12H11Br2NO3 6h were synthesized, validated by 1HNMR, 13CNMR, FT-IR, UVVis, EIMS spectroscopic techniques and confirmed by using single crystal X-ray diffraction (SC-XRD) study. The DFT and TDDFT calculations at B3LYP/6-311 + G(d,p) level of theory were performed for comparative analysis of spectroscopic data, optimized geometries, frontier molecular orbitals (FMOs), natural bond orbital (NBO) analysis and nonlinear optical (NLO) properties of 5m, 6e, 6h and 6o. Overall, experimental findings were supported nicely by corresponding DFT computed results. The NBO analysis confirmed that the presence of non-covalent interactions, hydrogen bonding and hyper- conjugative interactions are pivotal cause for the existence of 5m, 6e, 6h and 6o in the solid-state. NLO analysis showed that 5m, 6e, 6h and 6o have significant NLO properties as compared to prototype standard compound which disclosed their potential for technology related applications.

Chiral Pool-Based Synthesis of Naphtho-Fused Isocoumarins

A variety of chiral derivatives of benzo[d]naphtho[1,2-b]pyran-6-one were prepared in a single step by Et3N-mediated condensation of homophthalic anhydride with different derivatives of (S)-amino acid chlorides at -5 °C by employing a chiral pool methodology. Chirality 27:951-957, 2015.

Iron-Catalyzed Enantioselective Cross-Coupling Reactions of α-Chloroesters with Aryl Grignard Reagents

The first iron-catalyzed enantioselective cross-coupling reaction between an organometallic compound and an organic electrophile is reported. Synthetically versatile racemic α-chloro- and α-bromoalkanoates were coupled with aryl Grignard reagents in the presence of catalytic amounts of an iron salt and a chiral bisphosphine ligand, giving the products in high yields with acceptable and synthetically useful enantioselectivities (er up to 91:9). The produced α-arylalkanoates were readily converted to the corresponding α-arylalkanoic acids with high optical enrichment (er up to >99:1) via simple deprotections/recrystallizations. The results of radical probe experiments are consistent with a mechanism that involves the formation of an alkyl radical intermediate, which undergoes subsequent enantioconvergent arylation in an intermolecular manner. The developed asymmetric coupling offers not only facile and practical access to various chiral α-arylalkanoic acid derivatives, which are of significant pharmaceutical importance, but also a basis of controlling enantioselectivity in an iron-catalyzed organometallic transformation. (Chemical Equation Presented).

Chiron based synthesis of isocoumarins: Reactivity of α-substituted carboxylic acids

The asymmetric synthesis of a novel (S)-isocoumarin has been attempted in a single step by the coupling of homophthalic acid with (S)-N-protected amino acids and α-chloroacids at high temperature by exploiting a chiral pool methodology. The coupling of homophthalic acid with N-protected (S)-amino acids gave exclusion of the carboxyl/alkyl group. However, coupling of homophthalic acid with α-chloroacids afforded asymmetric isocoumarins in high yield.

Stereoselective synthesis of (3r)-3-alkyl-4,1-benzoxazepine-2,5-diones

Novel 3-alkyl-4,1-benzoxazepine-2,5-diones were synthesized in good ee exploiting the chiral pool methodology, an economical way of asymmetric synthesis. Various anthranilic acids are coupled with different α-haloacids to afford N-acylated anthranilic aci

Enantioselective CC bond reduction of unsaturated α-chloro esters by old yellow enzymes

The reduction of the CC double bond of some unsaturated α-chloro esters was investigated by means of cloned and overexpressed enoate reductases. The results were compared with those obtained by employing baker's yeast whole cells. The anti stereochemistry of hydrogen additions was confirmed by deuterium labeling experiments.

Synthesis of azide-alkyne fragments for "Click" chemical applications. Part 2. Formation of oligomers from orthogonally protected chiral trialkylsilylhomopropargyl azides and homopropargyl alcohols

(Chemical Equation Presented) A small library of chiral, β3-substituted homopropargyl alcohols and chiral β3-substituted trimethylsilylhomopropargyl azides were generated starting from natural L-amino acids. The free alkynes and azides were then coupled, using a Huisgen 1,3-dipolar cycloaddition, to provide chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as potential peptidomimetic compounds. The work is an extension to the previous synthesis of racemic, orthogonally protected 1,4-disubstituted-1,2,3-triazoles from the corresponding α-substituted propargyl alcohols and α-substituted trialkylsilylpropargyl azides.

Stereoselective synthesis of chiral 4-(1-Chloroalkyl)-β-lactams starting from amino acids and their transformation into functionalized chiral azetidines and pyrrolidines

Chiral short-chain α-chloroaldehydes were prepared starting from enantiomerically pure amino acids in a three-step approach, thus providing a practical synthetic alternative for known organocatalytic α-chlorination procedures. The latter aldehydes proved

An unusual conformation of α-haloamides due to cooperative binding with zincated porphyrins

CD and NMR spectroscopic evidence of cooperative binding between an α-halogen atom and a carboxamide group with a zinc porphyrin leads to an unprecedented conformation for the determination of the absolute stereochemistry of α-haloamides (α-halocarboxylic acids derivatized with 1,4-phenylenediamine) through the use of exciton-coupled circular dichroism (ECCD). With the use of chiral lactams, whose rotomeric contributions are minimized, both ECCD and NMR spectroscopy demonstrate that the porphyrin favors binding to the side of the sterically more demanding halogen atom as compared to the smaller hydrogen atom. In all, the data is strongly suggestive of an unusual conformation not observed before for α-chiral amides. A mnemonic for determining the absolute stereochemistry of α-halogenated carboxylic acids is provided.

Liquid crystal dimers derived from naturally occurring chiral moieties: synthesis and characterization

Naturally occurring cholesterol and α-chloroalkanoyl units derived from natural α-amino acids (l-valine, l-leucine, and l-isoleucine) have been utilized to prepare three different series of nonsymmetric liquid crystal dimers. Tolane (diphenylacetylene), w