(1R,4r)-4-[(1R)-1-{[(tert-butoxy)carbonyl]amino}ethyl]cyclohexane-1-carboxylic acid

• ChemBase ID: 162505
• Molecular Formular: C14H25NO4
• Molecular Mass: 271.3526
• Monoisotopic Mass: 271.17835829
• SMILES: [C@@H]1(CC[C@@H](CC1)[C@H](NC(=O)OC(C)(C)C)C)C(=O)O
• Canonical SMILES: C[C@H]([C@@H]1CC[C@H](CC1)C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C14H25NO4/c1-9(15-13(18)19-14(2,3)4)10-5-7-11(8-6-10)12(16)17/h9-11H,5-8H2,1-4H3,(H,15,18)(H,16,17)/t9-,10-,11-/m1/s1
• InChIKey: KLCGIONZGDCLMV-GMTAPVOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4r)-4-[(1R)-1-{[(tert-butoxy)carbonyl]amino}ethyl]cyclohexane-1-carboxylic acid
• IUPAC Traditional name: (1R,4r)-4-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]cyclohexane-1-carboxylic acid
• Synonyms: trans-4-[(1R)-1-[[(1,1-Dimethylethoxy)carbonyl]amino]ethyl]cyclohexanecarboxylic Acid; trans-4-[(R)-1-[(tert-Butyloxycarbonyl)amino]ethyl]cyclohexanecarboxylic Acid; (1R)-trans-4-[N-Boc-1-aminoethyl]cyclohexanecarboxylic Acid (~90% R)

Database IDs

• CAS Number: 671815-99-9
• PubChem SID: 162256640
• PubChem CID: 54589769

CALCULATED PROPERTIES

• Acid pKa: 4.259586
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.3577778
• LogD (pH = 7.4): -0.3718013
• Log P: 2.6202414
• Molar Refractivity: 71.1955 cm^3
• Polarizability: 28.24244 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 125-128°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B618690

Intermediate in the production of Rho kinase inhibitors and neurite outgrowth promoters.

REFERENCES

• Gingras, K., et al.: Bioorg. Med. Chem. Lett., 14, 4931 (2004)