3-Fluoro-L-β-homophenylalanine hydrochloride
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3-Fluoro-L-β-homophenylalanine hydrochloride

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Category
Fluorinated amino acids
Catalog number
BAT-006789
CAS number
331763-64-5
Molecular Formula
C10H13ClFNO2
Molecular Weight
233.67
3-Fluoro-L-β-homophenylalanine hydrochloride
IUPAC Name
(3S)-3-amino-4-(3-fluorophenyl)butanoic acid;hydrochloride
Synonyms
H-Phe(3-F)-(C#CH2)OH HCl; (S)-3-Amino-4-(3-fluorophenyl)butanoic acid hydrochloride
Related CAS
270596-50-4 (free base)
Purity
95%
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H12FNO2.ClH/c11-8-3-1-2-7(4-8)5-9(12)6-10(13)14;/h1-4,9H,5-6,12H2,(H,13,14);1H/t9-;/m0./s1
InChI Key
HLJRPTAKNOUJAW-FVGYRXGTSA-N
Canonical SMILES
C1=CC(=CC(=C1)F)CC(CC(=O)O)N.Cl
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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