2,3,4,5,6-Pentafluoro-D-phenylalanine
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2,3,4,5,6-Pentafluoro-D-phenylalanine

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Category
Fluorinated amino acids
Catalog number
BAT-006705
CAS number
40332-58-9
Molecular Formula
C9H6F5NO2
Molecular Weight
255.15
2,3,4,5,6-Pentafluoro-D-phenylalanine
IUPAC Name
(2R)-2-amino-3-(2,3,4,5,6-pentafluorophenyl)propanoic acid
Synonyms
H-D-Phe(F5)-OH; (R)-2-Amino-3-(perfluorophenyl)propanoic acid
Appearance
White Powder
Purity
≥ 98%
Density
1.609g/cm3
Boiling Point
286.3°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C9H6F5NO2/c10-4-2(1-3(15)9(16)17)5(11)7(13)8(14)6(4)12/h3H,1,15H2,(H,16,17)/t3-/m1/s1
InChI Key
YYTDJPUFAVPHQA-GSVOUGTGSA-N
Canonical SMILES
C(C1=C(C(=C(C(=C1F)F)F)F)F)C(C(=O)O)N
1. 3,3,6,6-Tetra-methyl-9-[6-(3,3,6,6-tetra-methyl-1,8-dioxo-2,3,4,5,6,7,8,9-octa-hydro-1H-xanthen-9-yl)pyridin-2-yl]-2,3,4,5,6,7,8,9-octa-hydro-1H-xanthene-1,8-dione
Antar A Abdelhamid, Shaaban Kamel Mohamed, Mirze A Allahverdiyev, Atash V Gurbanov, Seik Weng Ng Acta Crystallogr Sect E Struct Rep Online. 2011 Apr 1;67(Pt 4):o785. doi: 10.1107/S1600536811007318. Epub 2011 Mar 5.
In the title mol-ecule, C(39)H(45)NO(6), the two tetra-methyl-octa-hydroxanthen-1,8-dione substituents are arranged approximately parallel to each other and approximately perpendicular to the plane of the pyridine ring. The six-membered xanthene rings adopt flattened boat conformations with the O and methine C atoms deviating from the plane of the other four atoms.
2. (Carbazol-9-ido-κ N)di-chlorido-(η5:η1-2,3,4,5-tetra-methyl-penta-fulvene)tantalum(V)
Simon de Graaff, Aylişa Elma, Marc Schmidtmann, Rüdiger Beckhaus IUCrdata. 2022 Dec 23;7(Pt 12):x221201. doi: 10.1107/S2414314622012019. eCollection 2022 Dec.
The reaction of (η5:η1-2,3,4,5-tetra-methyl-penta-fulvene)tantalum(V) dicarbazolide chloride (1) with etheric HCl results in the formation of the title compound (2), [Ta(C10H14)(C12H8N)Cl2]. The TaV atom has a distorted tetra-hedral coordination environment in a three-legged piano-stool fashion. The conformation of the penta-fulvene exocyclic C atom to the three other ligands is staggered and not eclipsed, as found in the crystal structure of 1. Inter-molecular inter-actions include π-π stacking, H⋯π inter-actions and weak C-H⋯Cl hydrogen bonds.
3. 1,5-ethano-2,3,4,5-tetrahydro-1H-3-benzazepines
L A Walter, W K Chang J Med Chem. 1975 Feb;18(2):206-8. doi: 10.1021/jm00236a022.
1,5-Ethano-2,3,4,5-tetrahydro-1H-3-benzazepine, from the LiA1H4 reduction of 2-benzyloxy-1,5-ethano-4-oxo-2,3,4,5-tetrahydro-1H-3-benzazepine, was converted to N-alkyl, aralkyl, cycloalkyl, and alkenyl derivatives which were inactive as morphine type analgetics in mice. The LiA1H4 reduction of 2-benzyloxy-1,5-etheno-4-oxo-2,3,4,5-tetrahydro-1H-3-benzazepine gave unstable products from which only the skeletally rearranged dihydro- and tetrahydrobenzo[e]isoindolines, were isolated.
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