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Chemical Structure| 18927-05-4
Chemical Structure| 18927-05-4
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Product Details of [ 18927-05-4 ]

CAS No. :18927-05-4 MDL No. :MFCD00017205
Formula : C10H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :BSVIOYCZTJRBDB-UHFFFAOYSA-N
M.W : 180.20 Pubchem ID :519609
Synonyms :

Calculated chemistry of [ 18927-05-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.8
TPSA : 35.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.35
Log Po/w (XLOGP3) : 1.83
Log Po/w (WLOGP) : 1.41
Log Po/w (MLOGP) : 1.67
Log Po/w (SILICOS-IT) : 2.06
Consensus Log Po/w : 1.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.19
Solubility : 1.17 mg/ml ; 0.00649 mol/l
Class : Soluble
Log S (Ali) : -2.2
Solubility : 1.15 mg/ml ; 0.00636 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.178 mg/ml ; 0.000989 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 18927-05-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 18927-05-4 ]

* 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 [ 18927-05-4 ]
  • Downstream synthetic route of [ 18927-05-4 ]

[ 18927-05-4 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 18927-05-4 ]
  • [ 5020-41-7 ]
YieldReaction ConditionsOperation in experiment
80% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1 h; Step 1 : Synthesis of 2-(3-methoxyphenyl)ethan-l-ol: [0980] To a stirred solution of methyl 2-(3-methoxyphenyl)acetate (5 g, 27.77 mmol) in dry THF (50 mL) at 0 °C, LAH 1M in THF (42 mL, 41.66 mmol) was added and the reaction was stirred at 0 °C for 1 h. The progress of the reaction was monitored by TLC. Upon completion the reaction mass was quenched with aqueous saturated aqueous sodium sulphate solution and filtered. The filtrate was concentrated to dryness under reduced pressure. The residue obtained was diluted with water and extracted with DCM. The combined organic layers were dried over Na2S04 and concentrated under reduced pressure. The crude compound was purified by column chromatography to afford the title compound (3.4 g, 80percent).
68% With sodium tetrahydroborate; calcium chloride In ethanol; water for 1.5 h; (3-Methoxy-phenyl)-acetic acid methyl ester (2.5 g, 13.9 mmol) was dissolved in EtOH/H2O (40/10 mL), and CaCl2 (1.5 g, 13.9 mmol) was added thereto. Thereafter, when the solids were completely dissolved, NaBH4 (1.1 g, 27.8 mmol) was slowly added. The resulting mixture was stirred for 1 hour and a half, and water and 2 N HCl were added to be adjusted to pH 3 to 4, and then concentrated. The mixture was diluted with water, and extracted with dichloromethane. An organic layer was dried over sodium sulfate, and concentrated under reduced pressure. Then, the residue was purified using silica gel chromatography to obtain the title compound (colorless oil, 1.44 g, and 68percent yield). (0101) 1H NMR (300 MHz, CDCl3) δ 7.24 (t, 1H), 6.78 - 6.84 (m, 3H), 3.85 (m, 2H), 3.79 (s, 3H), 2.85 (t, 2H), 1.52 (br s, 1H).
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 7, p. 2785 - 2788
[2] Chemistry - A European Journal, 2015, vol. 21, # 42, p. 14737 - 14741
[3] Patent: WO2015/10049, 2015, A1, . Location in patent: Paragraph 0979; 0980
[4] Patent: EP2963027, 2016, A1, . Location in patent: Paragraph 0099; 0100; 0101
[5] Synthesis, 1999, # 5, p. 885 - 897
[6] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3719 - 3735
  • 2
  • [ 18927-05-4 ]
  • [ 74-88-4 ]
  • [ 32454-33-4 ]
Reference: [1] Helvetica Chimica Acta, 1971, vol. 54, p. 868 - 897
[2] Patent: WO2009/42694, 2009, A1, . Location in patent: Page/Page column 118-119
[3] Patent: WO2007/56497, 2007, A1, . Location in patent: Page/Page column 51-52
  • 3
  • [ 18927-05-4 ]
  • [ 1798-09-0 ]
Reference: [1] Synthesis, 1981, # 2, p. 126 - 127
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 11, p. 2575 - 2582
  • 4
  • [ 67-56-1 ]
  • [ 1798-09-0 ]
  • [ 18927-05-4 ]
YieldReaction ConditionsOperation in experiment
100% for 16 h; Heating / reflux Methyl (3-methoxyphenyl)acetate; A solution of 25.0 g (150 ml) of (3-methoxyphenyl)acetic acid in dry methanol (250 ml) was mixed with 2 ml of cone, sulfuric acid and heated under reflux for 16 h. The cooled reaction solution was concentrated in vacuo, added to ice-water and extracted four times with 70 ml of ethyl acetate each time. The combined organic extracts were washed with saturated NaCI solution and dried over magnesium sulfate, and the solvent was removed in vacuo. Yield: 28.3 g (100percent) of colorless oil 1H-NMR (DMSOd6): 3.61 (s, 3H), 3.64 (s, 2H), 3.74 (s, 3H), 6.80-6.86 (m, 3H), 7.19- 7.25 (m, 1 H). MS (API-ES,pos) m/z = 181 [M+H]+
100% Reflux General procedure: To an appropriately substituted phenylacetic acid (10 mmol) dissolved in dried methanol (50 mL), concentrated sulfuric acid (0.5 mL) was added dropwise.The mixture was refluxed from 7 to 9 h. Next, the solvent was evaporated, and residue was dissolved in 40 mL of ethyl acetate, washed with 0.5percent NaOH andbrine. Organic layer was dried over anhydrous Na2SO4 and filtered. The solvent was evaporated to give the products as colorless oils.
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 13, p. 2843 - 2866
[2] Patent: WO2008/25736, 2008, A1, . Location in patent: Page/Page column 64
[3] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 117 - 124
[4] Organic Letters, 2017, vol. 19, # 17, p. 4632 - 4635
[5] Tetrahedron Letters, 2001, vol. 42, # 24, p. 3959 - 3961
[6] Journal of Physical Chemistry B, 2010, vol. 114, # 20, p. 6968 - 6972
[7] Tetrahedron, 1995, vol. 51, # 45, p. 12211 - 12216
[8] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 7, p. 1757 - 1766
[9] Tetrahedron Letters, 2003, vol. 44, # 2, p. 331 - 334
[10] Journal fuer Praktische Chemie/Chemiker-Zeitung, 1998, vol. 340, # 6, p. 530 - 535
[11] Helvetica Chimica Acta, 1971, vol. 54, p. 868 - 897
[12] Tetrahedron, 2009, vol. 65, # 33, p. 6600 - 6610
[13] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1130 - 1135
[14] Journal of the Brazilian Chemical Society, 2012, vol. 23, # 5, p. 854 - 860
[15] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 8, p. 2741 - 2747
[16] Medicinal Chemistry Research, 2012, vol. 21, # 11, p. 3885 - 3896
[17] Russian Journal of Bioorganic Chemistry, 2015, vol. 41, # 2, p. 170 - 177
[18] Australian Journal of Chemistry, 2012, vol. 65, # 10, p. 1413 - 1419,7
[19] Australian Journal of Chemistry, 2012, vol. 65, # 10, p. 1413 - 1419
[20] CrystEngComm, 2014, vol. 16, # 2, p. 164 - 174
[21] Chemistry - A European Journal, 2015, vol. 21, # 7, p. 2785 - 2788
[22] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3719 - 3735
  • 5
  • [ 1798-09-0 ]
  • [ 18927-05-4 ]
YieldReaction ConditionsOperation in experiment
97% With chloro-trimethyl-silane In methanol; ethyl acetate Step 1.
Preparation of Methyl 3-methoxyphenylacetate
Trimethylsilyl chloride (182 g, 1.68 mol) was added dropwise to a solution of 3-methoxyphenylacetic acid (127 g, 0.77 mol) in methanol (1.0 L) over 1.1 hours.
The reaction was stirred at room temperature for 17.25 hours, concentrated in vacuo, dissolved in ethyl acetate, dried over MgSO4, and concentrated in vacuo, to give a brown oil (133 g, 97percent): 1 H NMR (CDCl3 /300 MHz) 7.24 (t, 1H, J=7.5 Hz), 6.83 (m, 3H), 3.80 (s, 3H), 3.69 (s, 3H), 3.60 (s, 2H).
Reference: [1] Patent: US6077850, 2000, A,
  • 6
  • [ 67-56-1 ]
  • [ 586-37-8 ]
  • [ 18927-05-4 ]
Reference: [1] Synthesis, 1981, # 2, p. 126 - 127
  • 7
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 6971-51-3 ]
  • [ 616-38-6 ]
  • [ 18927-05-4 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 5, p. 969 - 972
  • 8
  • [ 84508-57-6 ]
  • [ 18927-05-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 11, p. 2575 - 2582
  • 9
  • [ 100-84-5 ]
  • [ 18927-05-4 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 12, p. 2763 - 2770
[2] Tetrahedron, 1998, vol. 54, # 12, p. 2763 - 2770
  • 10
  • [ 66947-60-2 ]
  • [ 124-41-4 ]
  • [ 18927-05-4 ]
Reference: [1] Helvetica Chimica Acta, 1998, vol. 81, # 2, p. 251 - 267
  • 11
  • [ 5000-65-7 ]
  • [ 18927-05-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 11, p. 2575 - 2582
  • 12
  • [ 22246-27-1 ]
  • [ 124-41-4 ]
  • [ 18927-05-4 ]
  • [ 35598-05-1 ]
Reference: [1] Helvetica Chimica Acta, 1998, vol. 81, # 2, p. 251 - 267
  • 13
  • [ 186581-53-3 ]
  • [ 1798-09-0 ]
  • [ 18927-05-4 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 12, p. 2763 - 2770
  • 14
  • [ 67-56-1 ]
  • [ 1360789-10-1 ]
  • [ 18927-05-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 548 - 551
  • 15
  • [ 22246-27-1 ]
  • [ 124-41-4 ]
  • [ 18927-05-4 ]
  • [ 35598-05-1 ]
Reference: [1] Helvetica Chimica Acta, 1998, vol. 81, # 2, p. 251 - 267
  • 16
  • [ 18927-05-4 ]
  • [ 33543-62-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 7, p. 1757 - 1766
  • 17
  • [ 18927-05-4 ]
  • [ 75534-35-9 ]
Reference: [1] Patent: EP2963027, 2016, A1,
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