(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetic acid

• ChemBase ID: 151155
• Molecular Formular: C8H11NO2
• Molecular Mass: 153.17844
• Monoisotopic Mass: 153.0789786
• SMILES: C1C=CCC(=C1)[C@H](C(=O)O)N
• Canonical SMILES: N[C@H](C1=CCC=CC1)C(=O)O
• InChI: InChI=1S/C8H11NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-2,5,7H,3-4,9H2,(H,10,11)/t7-/m1/s1
• InChIKey: JBJJTCGQCRGNOL-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetic acid
• IUPAC Traditional name: (R)-amino(cyclohexa-1,4-dien-1-yl)acetic acid
• Synonyms: (R)-α-Amino-1,4-cyclohexadiene-1-acetic acid; (R)-(-)-2-(2,5-Dihydrophenyl)glycine; (R)-alpha-Amino-1-(1,4-cyclohexadienyl)acetic acid; (-)-2,5-Dihydro-D-phenylglycine; (R)-2-Amino-2-(cyclohexa-1,4-dien-1-yl)acetic acid; (R)-α-氨基-1,4-环己二烯-1-乙酸; (R)-(-)-2-(2,5-二氢苯基)甘氨酸; D-(-)-二氢苯基甘氨酸

Database IDs

• CAS Number: 26774-88-9
• EC Number: 247-999-1
• MDL Number: MFCD00137746
• Beilstein Number: 2091420
• PubChem SID: 24870728; 162245313
• PubChem CID: 1268102

CALCULATED PROPERTIES

• Acid pKa: 2.456461
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.7716335
• LogD (pH = 7.4): -1.7817342
• Log P: -1.7717015
• Molar Refractivity: 43.3833 cm^3
• Polarizability: 16.29506 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 280 °C (dec.)(lit.); 288-290°C subl.
• Optical Rotation: [α]20/D -154°, c = 1 in H2O; -160 (c=1 in 1N HCl)

Safety Information

• German water hazard class: 3
• TSCA Listed: 否

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C8H11NO2

DETAILS

Sigma Aldrich - 471380

Packaging
5 g in glass bottle

REFERENCES

• ?-Lactam antibiotic side-chain.