L-β-Homoalaninol hydrochloride
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L-β-Homoalaninol hydrochloride

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Category
Amino Alcohol
Catalog number
BAT-002643
CAS number
863304-89-6
Molecular Formula
C4H12ClNO
Molecular Weight
125.60
L-β-Homoalaninol hydrochloride
IUPAC Name
(3S)-3-aminobutan-1-ol;hydrochloride
Synonyms
H-β-homoAla-ol HCl; H-β-Hal-ol HCl; (S)-3-Amino-1-butanol hydrochloride; (3S)-3-aminobutan-1-ol hydrochloride
Purity
≥ 95%
InChI
InChI=1S/C4H11NO.ClH/c1-4(5)2-3-6;/h4,6H,2-3,5H2,1H3;1H/t4-;/m0./s1
InChI Key
FMMFLYBTRIVTPX-WCCKRBBISA-N
Canonical SMILES
CC(CCO)N.Cl

L-β-Homoalaninol hydrochloride, a versatile compound with diverse applications in research and pharmaceutical domains, boasts varied utility. Here are the key applications presented with a high degree of perplexity and burstiness:

Synthetic Organic Chemistry: Positioned as a cornerstone in the realm of synthetic organic chemistry, L-β-Homoalaninol hydrochloride serves as a fundamental building block in crafting intricate organic molecules and pharmaceutical agents. Chemists employ this compound adeptly to incorporate hydroxyl and alkyl groups with precision into target molecules harnessing its reactive nature to forge novel chemical entities for drug development and advancements in material science.

Peptide Synthesis: In the intricate world of peptide synthesis, L-β-Homoalaninol hydrochloride plays a pivotal role in fashioning modified peptides and peptidomimetics. The artistry of peptide synthesis necessitates the utilization of specific amino alcohols like this compound to fabricate stable biologically active peptides with enhanced characteristics. These synthetic peptides emerge as potent therapeutic agents formidable enzyme inhibitors and invaluable molecular probes shaping the landscape of bioactive compounds.

Pharmaceutical Development: Unveiling its significance in the spectrum of pharmaceutical development, L-β-Homoalaninol hydrochloride emerges as a crucial intermediate in drug discovery particularly in the realm of medications targeting metabolic disorders or possessing antimicrobial properties. Its unique structural composition enables its integration into the formulation of novel drug candidates through meticulous structure-activity relationship investigations. This endeavor catalyzes the unveiling of efficacious and safer pharmaceutical modalities heralding breakthroughs in therapeutic interventions.

Chiral Auxiliary: Embarking on the frontier of asymmetric synthesis, L-β-Homoalaninol hydrochloride assumes the role of a distinguished chiral auxiliary orchestrating stereochemistry in chemical reactions with finesse. Through the strategic deployment of this compound, chemists unlock the door to high enantioselectivity in the synthesis of chiral molecules essential building blocks in the development of pharmaceuticals agrochemicals and fine chemicals endowed with precise biological activities.

1. 1-Haloacylpiperazines
S Groszkowski, J Sienkiewicz, L Korzycka Pol J Pharmacol Pharm. 1975 Apr-Jun;27(2):183-6.
By direct acylation of piperazine with halogenocarboxylic acid chlorides in acid medium, the hydrochlorides of 1-haloacylpiperazines were obtained.
2. Metal-free and regiospecific synthesis of 3-arylindoles
Chuangchuang Xu, Wenlai Xie, Jiaxi Xu Org Biomol Chem. 2020 Apr 8;18(14):2661-2671. doi: 10.1039/d0ob00317d.
A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid-base co-catalysis, and broad substrate scope.
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