9H-fluoren-9-ylmethyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate

• ChemBase ID: 137242
• Molecular Formular: C20H23NO3
• Molecular Mass: 325.40152
• Monoisotopic Mass: 325.1677936
• SMILES: CC(C)[C@@H](CO)NC(=O)OCC1c2ccccc2c2c1cccc2
• Canonical SMILES: OC[C@H](C(C)C)NC(=O)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C20H23NO3/c1-13(2)19(11-22)21-20(23)24-12-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h3-10,13,18-19,22H,11-12H2,1-2H3,(H,21,23)/t19-/m1/s1
• InChIKey: MYMGENAMKAPEMT-LJQANCHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9H-fluoren-9-ylmethyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate
• IUPAC Traditional name: 9H-fluoren-9-ylmethyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate
• Synonyms: (S)-2-(Fmoc-amino)-3-methyl-1-butanol; N-(9-Fluorenylmethoxycarbonyl)-L-valinol; N-Fmoc-L-valinol; (S)-2-(Fmoc-氨基)-3-甲基-1-丁醇; N-(9-芴甲氧羰基)-L-缬氨醇; N-Fmoc-L-缬氨醇

Database IDs

• CAS Number: 160885-98-3
• MDL Number: MFCD00235961
• Beilstein Number: 7041232
• PubChem SID: 24871364; 162231507
• PubChem CID: 688273

CALCULATED PROPERTIES

• Acid pKa: 14.41964
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.6125379
• LogD (pH = 7.4): 3.6125376
• Log P: 3.6125379
• Molar Refractivity: 93.7053 cm^3
• Polarizability: 37.808975 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 129-133 °C; 129-133 °C(lit.)
• Optical Rotation: [α]20/D -20±1°, c = 1% in chloroform; [α]20/D -20°, c = 1 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0%; 97%
• Empirical Formula (Hill Notation): C20H23NO3

DETAILS

Sigma Aldrich - 445673

Application
Starting material for the synthesis of enantiopure homo-β-amino acids.1,2 Used in the efficient synthesis of enantiopure tetrahydroisoquinolines.3 Intermediate in the one-pot conversion of amino acid carbamates to N-derivatized 2-oxazolidinones.4