Fmoc-dopa(acetonide)-oh

C₂₇H₂₅NO₆CAS 852288-18-7459.50 g/mol

Open in Covalent MOL file

Acetal Carbamate Carboxylic acid Ether

Properties

Molecular formula: C₂₇H₂₅NO₆
Molar mass: 459.50 g/mol
Exact mass: 459.1682 Da
logP: 4.73Crippen estimate
Polar surface area: 94.1 Å²
H-bond donors / acceptors: 2 / 5
Rotatable bonds: 6
Stereocentres: Sin SMILES atom order

Hazards

Warning

H315 Causes skin irritation100% of notifiers
H319 Causes serious eye irritation100% of notifiers
H335 May cause respiratory irritation100% of notifiers

Aggregated from the ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501

Identifiers

CAS number

852288-18-7

SMILES

CC1(OC2=C(O1)C=C(C=C2)C[C@@H](C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)C

InChIKey

SHZLOTJPHMTVDI-QFIPXVFZSA-N

InChI

InChI=1S/C27H25NO6/c1-27(2)33-23-12-11-16(14-24(23)34-27)13-22(25(29)30)28-26(31)32-15-21-19-9-5-3-7-17(19)18-8-4-6-10-20(18)21/h3-12,14,21-22H,13,15H2,1-2H3,(H,28,31)(H,29,30)/t22-/m0/s1

Characterization data

Calculated from the structure, in the form journals print them.

¹H NMR

Predicted ¹H NMR (400 MHz, CDCl₃) δ 11.50 (br s, 1H), 7.65 (dd, J = 7.7, 1.6 Hz, 2H), 7.43 (m, J = 7.7, 1.6 Hz, 2H), 7.38 (m, J = 7.7, 1.6 Hz, 2H), 7.38 (m, J = 7.7, 1.6 Hz, 2H), 6.73 (m, J = 7.7 Hz, 1H), 6.69 (m, J = 7.7, 1.6 Hz, 1H), 6.65 (d, J = 1.6 Hz, 1H), 5.22 (td, J = 7.0, 5.0 Hz, 1H), 4.80 (br d, J = 5.0 Hz, 1H), 4.78 (d, J = 7.0 Hz, 2H), 3.31 (t, J = 7.0 Hz, 1H), 3.21 (d, J = 7.0 Hz, 2H), 1.86 (s, 6H).

¹³C NMR

Predicted ¹³C NMR (101 MHz, CDCl₃) δ 178.0, 156.3, 147.4, 145.3, 142.6, 139.4, 137.4, 127.4, 127.3, 126.9, 126.4, 121.8, 121.1, 114.9, 114.4, 79.4, 57.8, 43.9, 39.7, 27.8.

[M + H]+

[M + H]+ Calcd for C27H26NO6 460.1755

[M + Na]+

[M + Na]+ Calcd for C27H25NNaO6 482.1574

[M − H]−

[M − H]− Calcd for C27H24NO6 458.1609

Elemental analysis

Anal. Calcd for C27H25NO6: C, 70.58; H, 5.48; N, 3.05.