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[ CAS No. 166591-85-1 ] {[proInfo.proName]}

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Chemical Structure| 166591-85-1
Chemical Structure| 166591-85-1
Structure of 166591-85-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 166591-85-1 ]

CAS No. :166591-85-1 MDL No. :MFCD08274995
Formula : C15H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :KMTRFKAFNRHBCH-UHFFFAOYSA-N
M.W : 277.32 Pubchem ID :15280723
Synonyms :

Calculated chemistry of [ 166591-85-1 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.47
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 78.2
TPSA : 66.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 1.9
Log Po/w (MLOGP) : 1.83
Log Po/w (SILICOS-IT) : 1.47
Consensus Log Po/w : 2.02

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.05
Solubility : 0.245 mg/ml ; 0.000882 mol/l
Class : Soluble
Log S (Ali) : -3.49
Solubility : 0.0904 mg/ml ; 0.000326 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.6
Solubility : 0.689 mg/ml ; 0.00248 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.0

Safety of [ 166591-85-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 166591-85-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 166591-85-1 ]
  • Downstream synthetic route of [ 166591-85-1 ]

[ 166591-85-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 41034-52-0 ]
  • [ 24424-99-5 ]
  • [ 166591-85-1 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 0 - 20℃; To a stirring mixture of (±)-l,2,3,4-tetrahydroisoquinoline-l-carboxylic acid (150 mg, 0.85 mmol) and CH2C12 (1.69 mL) at 0 °C, add di-tert-butyldicarbonate (185 mg, 0.85 mmol) and triethylamine (177 xL, 1.27 mmol). Allow the mixture to warm to room temperature with stirring overnight. Add an aqueous solution of HCl (1.0 N) until the pH reaches 3.0, then extract the mixture with EtOAc (3 x 25 mL). Wash the combined organic phases with saturated aqueous NaCl (50 mL), dry over MgS04, filter, and concentrate the filtrate under reduced pressure to furnish the title compound (235 mg, 100percent yield). Mass spectrum (m/z): 222 (M + 2H - t-Bu)+, 300 (M + Na)+, 577 (2M + Na)+.
85% With triethylamine In tetrahydrofuran; water STEP A
N-[(1,1-Dimethylethoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
Di-tert-Butyldicarbonate (Boc2 O, 8.2 g, 37.6 mmol, 1.1 eq.) was added to a stirred solution of 1,2,3,4-tetrahydroisoquinaldic acid [prepared from isoquinoline-1carboxylic acid according to W. Solomon, J. Chem. Soc., 1947, 129), 6.0 g, 33.8 mmol]and NEt3 (5.2 ml, 37.6 mmol, 1.1 eq.) in 50 ml of tetrahydrofuran and 50 ml of water.
The mixture was stirred at room temperature for 16 hours, when tetrahydrofuran was evaporated.
The residual aqueous phase was acidified (solid citric acid) and the protected amino acid extracted with AcOEt (three times).
The combined organic layers were washed with brine, dried over MgSO4 and evaporated (20 Torr, 30° C. and 0.01 Torr, 20° C.) to afford 8.0 g (85percent) of the protected amino acid.
Reference: [1] Patent: WO2015/94902, 2015, A1, . Location in patent: Page/Page column 22
[2] European Journal of Medicinal Chemistry, 2001, vol. 36, # 3, p. 265 - 286
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 314 - 319
[4] Patent: US5391705, 1995, A,
  • 2
  • [ 486-73-7 ]
  • [ 166591-85-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 2001, vol. 36, # 3, p. 265 - 286
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 314 - 319
  • 3
  • [ 124-38-9 ]
  • [ 1359987-43-1 ]
  • [ 166591-85-1 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 5, p. 2159 - 2168
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