(3R)-2-[(9H-fluoren-9-ylmethoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

• ChemBase ID: 39016
• Molecular Formular: C25H21NO4
• Molecular Mass: 399.43854
• Monoisotopic Mass: 399.14705816
• SMILES: c1ccc2c(c1)C[C@@H](N(C2)C(=O)OCC1c2c(c3c1cccc3)cccc2)C(=O)O
• Canonical SMILES: OC(=O)[C@H]1Cc2ccccc2CN1C(=O)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C25H21NO4/c27-24(28)23-13-16-7-1-2-8-17(16)14-26(23)25(29)30-15-22-20-11-5-3-9-18(20)19-10-4-6-12-21(19)22/h1-12,22-23H,13-15H2,(H,27,28)/t23-/m1/s1
• InChIKey: LIRBCUNCXDZOOU-HSZRJFAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-2-[(9H-fluoren-9-ylmethoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• IUPAC Traditional name: (3R)-2-[(9H-fluoren-9-ylmethoxy)carbonyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
• Synonyms: Fmoc-L-Tic-OH; (S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, N-FMOC protected; (R)-N-Fmoc-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; Fmoc-D-Tic-OH; Fmoc-D-Tic-OH; (R)-N-芴甲氧羰基-1,2,3,4-四氢异喹啉-3-羧酸

Database IDs

• CAS Number: 136030-33-6; 130309-33-0
• MDL Number: MFCD00144345; MFCD00144368
• Beilstein Number: 7499344
• PubChem SID: 24870995; 161002323
• PubChem CID: 978342

CALCULATED PROPERTIES

• Acid pKa: 3.7727962
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.9480731
• LogD (pH = 7.4): 1.4018823
• Log P: 4.676547
• Molar Refractivity: 112.6474 cm^3
• Polarizability: 44.70569 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -25.0±2°, c = 0.6% in methanol

Safety Information

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

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C25H21NO4

DETAILS

Sigma Aldrich - 47437

Other Notes
FMOC-D-Tic is employed e.g. for the solid-phase synthesis of Bradykinin antagonists1,2