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[ CAS No. 2987-06-6 ] {[proInfo.proName]}

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Chemical Structure| 2987-06-6
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Product Details of [ 2987-06-6 ]

CAS No. :2987-06-6 MDL No. :MFCD10697867
Formula : C13H16O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FFGVIYUANJAFJS-UHFFFAOYSA-N
M.W : 204.27 Pubchem ID :10987369
Synonyms :

Calculated chemistry of [ 2987-06-6 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 59.42
TPSA : 26.3 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) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 1.81
Log Po/w (WLOGP) : 2.56
Log Po/w (MLOGP) : 1.93
Log Po/w (SILICOS-IT) : 3.19
Consensus Log Po/w : 2.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 0.924 mg/ml ; 0.00452 mol/l
Class : Soluble
Log S (Ali) : -1.98
Solubility : 2.13 mg/ml ; 0.0104 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.87
Solubility : 0.0274 mg/ml ; 0.000134 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 2987-06-6 ]

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 [ 2987-06-6 ]

* 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 [ 2987-06-6 ]
  • Downstream synthetic route of [ 2987-06-6 ]

[ 2987-06-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 92829-83-9 ]
  • [ 2987-06-6 ]
YieldReaction ConditionsOperation in experiment
95.2% With hydrogenchloride In tetrahydrofuran; water at 20℃; To a solution of 1-ethylene acetal-4-benzyloxy-cyclohexane (17) (3.13 g, 12.6 mmol) in 50 ml THF, aqueous hydrochloric acid (1N, 30 ml) was added at rt. The reaction was stirred overnight and neutralized with sodium bicarbonate (sat.). The product was extracted with ethyl acetate and the organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by the silica gel chromatography (20percent ethyl acetate in hexane) yielded 2.45 g (95.2percent) of the title ketone. 1H NMR (CDCl3) δ: 1.95-2.62 (8H, m, 4.x.-CH2-), 3.82 (1H, m, -CH-), 4.59 (2H, s, Ph-CH2-), 7.28-7.36 (5H, m, Ph-H).
19.2 g With hydrogenchloride In tetrahydrofuran; water at 20℃; for 18 h; Inert atmosphere [532] Into a 1 -L round-bottom flask, was placed 8-(benzyloxy)-l,4-dioxaspiro[4.5]decane (40 g, 161.08 mmol, 1.00 equiv), HC1 (6N, 400 mL, 2.50 equiv), tetrahydrofuran (300 mL). The resulting solution was stirred for 18 h at room temperature. The resulting solution was extracted with ethyl acetate (200mL x 3) and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/hexane (1 : 10). This resulted in 19.2 g (58percent) of 4-(benzyloxy)cyclohexan-l - one as yellow oil. MS (ES, m/z) [M+H]+: 205.
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 9, p. 1799 - 1802
[2] Tetrahedron, 2003, vol. 59, # 45, p. 8989 - 8999
[3] Journal of the American Chemical Society, 2017, vol. 139, # 7, p. 2577 - 2580
[4] Patent: US2006/292073, 2006, A1, . Location in patent: Page/Page column 12
[5] Canadian Journal of Chemistry, 2003, vol. 81, # 1, p. 81 - 108
[6] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7706 - 7719
[7] New Journal of Chemistry, 2017, vol. 41, # 4, p. 1421 - 1424
[8] Angewandte Chemie - International Edition, 2016, vol. 55, # 5, p. 1816 - 1819[9] Angew. Chem., 2016, vol. 128, # 5, p. 1848 - 1851,4
[10] Journal of the Chemical Society - Series Chemical Communications, 1984, vol. NO. 11, p. 721 - 723
[11] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 3881 - 3886
[12] Canadian Journal of Chemistry, 1994, vol. 72, # 7, p. 1699 - 1704
[13] Patent: US5808146, 1998, A,
[14] Patent: US5817776, 1998, A,
[15] Patent: WO2011/7146, 2011, A1, . Location in patent: Page/Page column 61
[16] Patent: WO2012/151343, 2012, A1, . Location in patent: Page/Page column 33
[17] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 851 - 856
[18] Patent: WO2015/138220, 2015, A1, . Location in patent: Page/Page column 78
[19] Patent: WO2017/205296, 2017, A1, . Location in patent: Paragraph 532
[20] Patent: KR101905722, 2018, B1, . Location in patent: Paragraph 0122; 0126
  • 2
  • [ 2976-80-9 ]
  • [ 2987-06-6 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 18, p. 6851 - 6858
[2] Synthetic Communications, 1996, vol. 26, # 9, p. 1789 - 1792
[3] Journal of the American Chemical Society, [4] Journal of the American Chemical Society, 2009, vol. 131, p. 251 - 262
[5] Organic Syntheses, 2012, vol. 89, p. 105 - 114
[6] Journal of the American Chemical Society, 1995, vol. 117, # 23, p. 6210 - 6217
[7] Chemistry - A European Journal, 2017, vol. 23, # 65, p. 16574 - 16585
[8] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1973, p. 2165 - 2173
[9] Gazzetta Chimica Italiana, 1965, vol. 95, p. 438 - 447
[10] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 46 - 47
[11] Tetrahedron, 2000, vol. 56, # 38, p. 7513 - 7524
[12] Macromolecules, 2013, vol. 46, # 12, p. 4829 - 4838
  • 3
  • [ 22428-87-1 ]
  • [ 100-39-0 ]
  • [ 2987-06-6 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 6 h;
Stage #2: at 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran; water; mineral oil at 20℃; for 6 h;
4-(Benzyloxy)cyclohexanone (14-2): A 60percent dispersion of sodium hydride in mineral oil (760 mg, 23 mmol, 1.2 equiv) was added to a solution of l ,4-Dioxaspiro[4.5]decan-8-ol (14-1) (3.0 g, 19 mmol, 1.0 equiv) in anhydrous THF (50 mL) at 0 °C. After 6 hours benzyl bromide (2.5 mL, 21.3 mmol, 1.1 equiv) was added to the mixture. The mixture was stirred at room temperature overnight. A 4N HCl solution (30 mL) was added and the reaction was stirred at room temperature for an additional 6 hours. The reaction was neutralized to pH ~7 with 4N sodium hydroxide and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on an AnaLogix automated column chromatography system eluting with gradient of 0 to 30percent ethyl acetate in heptanes to give 14-2 (3.0 g, 77percent yield) as a light yellow oil.
Reference: [1] Patent: WO2012/151343, 2012, A1, . Location in patent: Page/Page column 36
[2] Journal of Organic Chemistry, 1970, vol. 35, # 5, p. 1525 - 1534
  • 4
  • [ 13482-22-9 ]
  • [ 100-44-7 ]
  • [ 2987-06-6 ]
Reference: [1] Patent: US2005/208093, 2005, A1, . Location in patent: Page/Page column 8
  • 5
  • [ 154410-53-4 ]
  • [ 2987-06-6 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 1, p. 57 - 60
  • 6
  • [ 556-48-9 ]
  • [ 2987-06-6 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 18, p. 6851 - 6858
[2] Tetrahedron, 2000, vol. 56, # 38, p. 7513 - 7524
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 46 - 47
[4] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1973, p. 2165 - 2173
[5] Gazzetta Chimica Italiana, 1965, vol. 95, p. 438 - 447
[6] Chemistry - A European Journal, 2017, vol. 23, # 65, p. 16574 - 16585
  • 7
  • [ 22428-87-1 ]
  • [ 2987-06-6 ]
Reference: [1] Canadian Journal of Chemistry, 2003, vol. 81, # 1, p. 81 - 108
[2] Canadian Journal of Chemistry, 1994, vol. 72, # 7, p. 1699 - 1704
[3] Journal of the Chemical Society - Series Chemical Communications, 1984, vol. NO. 11, p. 721 - 723
[4] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 3881 - 3886
[5] Patent: WO2011/7146, 2011, A1,
[6] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7706 - 7719
[7] Patent: WO2012/151343, 2012, A1,
[8] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 851 - 856
[9] Patent: WO2015/138220, 2015, A1,
[10] Angewandte Chemie - International Edition, 2016, vol. 55, # 5, p. 1816 - 1819[11] Angew. Chem., 2016, vol. 128, # 5, p. 1848 - 1851,4
[12] Journal of the American Chemical Society, 2017, vol. 139, # 7, p. 2577 - 2580
[13] Patent: WO2017/205296, 2017, A1,
[14] Patent: KR101905722, 2018, B1,
  • 8
  • [ 100-39-0 ]
  • [ 2987-06-6 ]
Reference: [1] Journal of the Chemical Society - Series Chemical Communications, 1984, vol. NO. 11, p. 721 - 723
[2] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 3881 - 3886
[3] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7706 - 7719
[4] Patent: WO2015/138220, 2015, A1,
[5] Journal of the American Chemical Society, 2017, vol. 139, # 7, p. 2577 - 2580
[6] Chemistry - A European Journal, 2017, vol. 23, # 65, p. 16574 - 16585
[7] Patent: WO2017/205296, 2017, A1,
  • 9
  • [ 4746-97-8 ]
  • [ 2987-06-6 ]
Reference: [1] Canadian Journal of Chemistry, 2003, vol. 81, # 1, p. 81 - 108
[2] Canadian Journal of Chemistry, 1994, vol. 72, # 7, p. 1699 - 1704
[3] Patent: WO2011/7146, 2011, A1,
[4] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7706 - 7719
[5] Patent: WO2012/151343, 2012, A1,
[6] Patent: WO2012/151343, 2012, A1,
[7] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 851 - 856
[8] Patent: WO2015/138220, 2015, A1,
[9] Angewandte Chemie - International Edition, 2016, vol. 55, # 5, p. 1816 - 1819[10] Angew. Chem., 2016, vol. 128, # 5, p. 1848 - 1851,4
[11] Patent: KR101905722, 2018, B1,
  • 10
  • [ 445481-11-8 ]
  • [ 2987-06-6 ]
  • [ 123990-98-7 ]
Reference: [1] Tetrahedron, 2000, vol. 56, # 38, p. 7513 - 7524
  • 11
  • [ 69125-55-9 ]
  • [ 2987-06-6 ]
Reference: [1] Journal of the Chemical Society - Series Chemical Communications, 1984, vol. NO. 11, p. 721 - 723
  • 12
  • [ 67-56-1 ]
  • [ 84029-18-5 ]
  • [ 2987-06-6 ]
  • [ 123990-98-7 ]
  • [ 127383-54-4 ]
  • [ 127383-53-3 ]
Reference: [1] Tetrahedron, 2000, vol. 56, # 38, p. 7513 - 7524
  • 13
  • [ 67-56-1 ]
  • [ 84049-33-2 ]
  • [ 2987-06-6 ]
  • [ 123990-98-7 ]
  • [ 127383-55-5 ]
  • [ 127383-54-4 ]
Reference: [1] Tetrahedron, 2000, vol. 56, # 38, p. 7513 - 7524
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