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[ CAS No. 4242-18-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 4242-18-6
Chemical Structure| 4242-18-6
Chemical Structure| 4242-18-6
Structure of 4242-18-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4242-18-6 ]

CAS No. :4242-18-6 MDL No. :MFCD01464030
Formula : C11H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GCFQXKYHWFWGSB-UHFFFAOYSA-N
M.W : 176.21 Pubchem ID :239604
Synonyms :

Calculated chemistry of [ 4242-18-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.83
TPSA : 37.3 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) : -5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 2.83
Log Po/w (WLOGP) : 2.26
Log Po/w (MLOGP) : 2.45
Log Po/w (SILICOS-IT) : 2.7
Consensus Log Po/w : 2.39

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.18 mg/ml ; 0.00102 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.0944 mg/ml ; 0.000536 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.88
Solubility : 0.234 mg/ml ; 0.00133 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 4242-18-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4242-18-6 ]

* 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 [ 4242-18-6 ]
  • Downstream synthetic route of [ 4242-18-6 ]

[ 4242-18-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 4242-18-6 ]
  • [ 41828-13-1 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 47, p. 15969 - 15982
[2] Patent: CN103864754, 2016, B,
[3] Patent: WO2017/156181, 2017, A1,
  • 2
  • [ 4242-18-6 ]
  • [ 917-54-4 ]
  • [ 13577-40-7 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 905,907
[2] Journal of Medicinal Chemistry, 1979, vol. 22, # 11, p. 1336 - 1340
  • 3
  • [ 4242-18-6 ]
  • [ 41790-30-1 ]
YieldReaction ConditionsOperation in experiment
100% With borane-THF In tetrahydrofuran at 0 - 20℃; for 16 h; 5,6,7,8-tetrahydronaphthalene 1-carboxylic acid (2.0 g, 11mmol) was dissolved in the tetrahydrofuran (following, THF) (30 mL), borane.THF (23 mL, a 0.98M THF solution, 23mmol) were added at 0 degree C, and it agitated at the room temperature for 16 hours. Water was added to the reaction solution at 0 degree C, and ethyl acetate extracted. The saturated sodium chloride solution washed the organic layer, and it condensed after drying with anhydrous sodium sulfate, and obtained the rough product. silica gel column chromatography (n-hexane -> n-hexane/ethyl acetate =3/1) refined the obtained rough product, and it obtained the title compound (1.9 g and colourless oil, quantitive)
99% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 24.5 h; To a solution of 1-tetrahydronaphthoic acid (5.70 g, 32.3 mmol) in THF (100 mL, dist. Na) at 0 °C was added lithium aluminium hydride (2.46 g, 64.7 mmol) in small portions. The reaction mixture was stirred at 0 °C for 30 min and then stirred for further 24 h at r.t. The reaction mixture was washed with water (100 mL) and extracted with EtOAc (3 x 50 mL). The organic phase was dried with Na2S04 and concentrated under reduced pressure to obtain 44 as colourless oil (5.23 g, 99percent). 1H NMR (CDC13) δ 7.18 (d, J = 7.4 Hz, 1H), 7.11 (d, J = 7.5 Hz, 1H), 7.05 (d, J = 7.6 Hz, 1H), 4.67 (s, 2H), 2.80 (t, J = 6.2 Hz, 2H), 2.76 (t, J = 6.4 Hz, 2H), 1.88- 1.77 (m, 4H). Found: [M+H-18]=145.5
98% With potassium hydrogensulfate; LiAlH4 In tetrahydrofuran; diethyl ether b
5,6,7,8-Tetrahydro-1-hydroxymethylnaphthalene
A solution of 20 mL (0.019 mol) of 1.0M LiAlH4 in Et2 O was cooled to -78° C. and treated dropwise with a solution of 3.42 g (0.019 mol) of 5,6,7,8-tetrahydro-1-naphthoic acid in 20 mL THF.
The solution was allowed to warm to room temperature and stirred overnight.
The solution was cooled to 0° C. and decomposed with 40 mL of a 0.43M solution of KHSO4.
The mixture was filtered through Celite and washed with EtOAc.
The organic phase was washed with 1N HCl and saturated NaCl.
Drying over MgSO4 and removal of the solvent under reduced pressure left 3.02 g (98percent yield) of the product.
The structure was confirmed by NMR spectroscopy.
Reference: [1] Patent: JP2016/222570, 2016, A, . Location in patent: Paragraph 0034
[2] Patent: WO2017/155909, 2017, A1, . Location in patent: Paragraph 0099
[3] Patent: US5610177, 1997, A,
[4] Tetrahedron, 1997, vol. 53, # 47, p. 15969 - 15982
[5] Patent: WO2017/156181, 2017, A1, . Location in patent: Paragraph 00349
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